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Showing metabocard for L-Tryptophan (HMDB0000929)

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enzymes (9)transporters (2) Show 11 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:59 UTC
HMDB IDHMDB0000929
Secondary Accession Numbers
  • HMDB00929
Metabolite Identification
Common NameL-Tryptophan
DescriptionTryptophan (Trp) or L-tryptophan is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tryptophan is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tryptophan is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tryptophan is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low-fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). Tryptophan is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Tryptophan is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized by tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn diets or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnup's disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnup's disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnup's disease. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed that consumption of tryptophan or 5-HTP may improve depression symptoms by increasing the level of serotonin in the brain. Tryptophan is sold over the counter in the United States (after being banned to varying extents between 1989 and 2005) and the United Kingdom as a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. It is also marketed as a prescription drug in some European countries for the treatment of major depression. There is evidence that blood tryptophan levels are unlikely to be altered by changing the diet, but consuming purified tryptophan increases the serotonin level in the brain, whereas eating foods containing tryptophan does not. This is because the transport system that brings tryptophan across the blood-brain barrier also transports other amino acids which are contained in protein food sources. Under certain situations, tryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of tryptophan can be found in glutaric aciduria type I (glutaric acidemia type I or GA1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan due to a deficiency of mitochondrial glutaryl-CoA dehydrogenase (EC 1.3.99.7, GCDH). Excessive levels of their intermediate breakdown products (e.g. glutaric acid, glutaryl-CoA, 3-hydroxyglutaric acid, glutaconic acid) can accumulate and cause damage to the brain (and also other organs), but particularly the basal ganglia. Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Other symptoms include spasticity (increased muscle tone/stiffness) and dystonia (involuntary muscle contractions resulting in abnormal movement or posture), but many affected individuals are asymptomatic. High levels of tryptophan have also been implicated in eosinophilia-myalgia syndrome (EMS), an incurable and sometimes fatal flu-like neurological condition linked to the ingestion of large amounts of L-tryptophan. The risk of developing EMS increases with larger doses of tryptophan and increasing age. Some research suggests that certain genetic polymorphisms may be related to the development of EMS. The presence of eosinophilia is a core feature of EMS, along with unusually severe myalgia (muscle pain). It is thought that both tryptophan and certain unidentified tryptophan contaminants may contribute to EMS (PMID: 1763543 ). It has also been suggested that excessive tryptophan or elevation of its metabolites could play a role in amplifying some of the pathological features of EMS (PMID: 10721094 ). This pathological damage is further augmented by metabolites of the kynurenine pathway (a tryptophan degradation pathway). Reduced levels of tryptophan in the blood are typically seen when individuals are fighting chronic infections, suffering from traumatic injuries (burns or wounds) or experiencing sepsis (PMID: 26309411 ). Tryptophan is mainly catabolized through the enzymatic activity of two enzymes: indoleamine-2,3-dioxygenase (IDO) 1 and IDO2, both of which are expressed widely in human tissues, and both of which are induced by interferon gamma (IFN-gamma or IFNG). IDO1 and IDO2 generate tryptophan catabolites such as kynurenine and kynurenic acid.  These tryptophan catabolites activate the aryl hydrocarbon receptor (AhR), which plays a key role immune regulation. The role of IDO1 and IDO2 is to effectively deplete tryptophan levels to starve infectious organisms (bacteria and parasites), thereby killing them or slowing their growth.  On the other hand, the AhR activation leads to a state of immunosuppression and is intended to serve as a brake on the immune (overexpression of IFNG and IL-1B) response to the infectious organisms.  Unfortunately, tryptophan starvation is often not effective against viruses or even all infectious microbes. As a result, this AhR activation by tryptophan catabolites can lead to a situation where viruses (or certain pathogens) continue to survive and multiply even while the immune system is effectively turning off. As a result, high levels of kynurenine and low levels of tryptophan (a high kynurenine to tryptophan ratio) can lead to or even be symptomatic of chronic viral or pathogenic infections or, at worse, sepsis and septic shock (PMID: 33338598 ; PMID: 21731667 ).
Structure
Data?1676999718
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000929 (L-Tryptophan)


  Mrv1652309042000142D          

 15 16  0  0  1  0            999 V2000
    0.0032   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -1.2545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -0.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4321   -1.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000929 (L-Tryptophan)

HMDB0000929
     RDKit          3D
L-Tryptophan
 27 28  0  0  0  0  0  0  0  0999 V2000
    2.9229   -1.8923    0.9590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0337   -0.9132    0.3555 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8356   -0.8118    1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    0.1406    0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    1.3963    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    1.9677    0.6301 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8532    1.0751   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    1.1611   -1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0884    0.0777   -2.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -1.0673   -1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417   -1.1227   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -0.0636   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    0.3671    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    0.4580    0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097    1.4627   -0.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259   -1.6078    0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239   -2.0377    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -1.2624   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452   -0.5671    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132   -1.8595    1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101    1.8689    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    2.9092    0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    2.0627   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.1991   -2.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.8770   -2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -2.0454   -0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.9815   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 12  4  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 15 27  1  0
M  END
Download

3D SDF for HMDB0000929 (L-Tryptophan)


  Mrv1652309042000142D          

 15 16  0  0  1  0            999 V2000
    0.0032   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -1.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900   -1.2545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -0.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644    0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124    1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -0.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4321   -1.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000929

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1

> <INCHI_KEY>
QIVBCDIJIAJPQS-VIFPVBQESA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.2252

> <EXACT_MASS>
204.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.047414013171778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-1.0854569138833579

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.1565885064574

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5439286383469866

> <JCHEM_PKA_STRONGEST_BASIC>
9.396082567807317

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
56.20280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-tryptophan

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000929 (L-Tryptophan)

HMDB0000929
     RDKit          3D
L-Tryptophan
 27 28  0  0  0  0  0  0  0  0999 V2000
    2.9229   -1.8923    0.9590 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0337   -0.9132    0.3555 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8356   -0.8118    1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    0.1406    0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    1.3963    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    1.9677    0.6301 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8532    1.0751   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8569    1.1611   -1.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0884    0.0777   -2.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -1.0673   -1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417   -1.1227   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -0.0636   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7470    0.3671    0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    0.4580    0.6640 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097    1.4627   -0.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259   -1.6078    0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239   -2.0377    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146   -1.2624   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452   -0.5671    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4132   -1.8595    1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101    1.8689    2.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    2.9092    0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    2.0627   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.1991   -2.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.8770   -2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -2.0454   -0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.9815   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 12  4  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  6
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 15 27  1  0
M  END
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PDB for HMDB0000929 (L-Tryptophan)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.006  -0.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.155  -2.022   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.661  -2.342   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.431  -1.008   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.401   0.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.877   1.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.938  -0.688   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.414   0.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.383   1.921   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.007   1.820   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.007   0.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.341  -0.490   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.673  -0.490   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.673  -2.030   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.340   0.280   0.000  0.00  0.00           C+0
CONECT    1    2    5   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    9                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8                                                       
CONECT   10   11                                                            
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    1                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
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3D PDB for HMDB0000929 (L-Tryptophan)

COMPND    HMDB0000929
HETATM    1  N1  UNL     1       2.923  -1.892   0.959  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.034  -0.913   0.356  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.836  -0.812   1.287  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.177   0.141   0.832  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.424   1.396   1.308  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.442   1.968   0.630  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.853   1.075  -0.288  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.857   1.161  -1.231  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.088   0.078  -2.082  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.333  -1.067  -1.991  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.342  -1.123  -1.044  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.086  -0.064  -0.183  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.747   0.367   0.262  1.00  0.00           C  
HETATM   14  O1  UNL     1       3.918   0.458   0.664  1.00  0.00           O  
HETATM   15  O2  UNL     1       2.110   1.463  -0.275  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.926  -1.608   0.900  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.724  -2.038   1.978  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.715  -1.262  -0.655  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.245  -0.567   2.294  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.413  -1.859   1.328  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.110   1.869   2.106  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.865   2.909   0.751  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.464   2.063  -1.313  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.891   0.199  -2.804  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.552  -1.877  -2.675  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.758  -2.045  -0.994  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.430   1.981  -1.084  1.00  0.00           H  
CONECT    1    2   16   17
CONECT    2    3   13   18
CONECT    3    4   19   20
CONECT    4    5    5   12
CONECT    5    6   21
CONECT    6    7   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   13   14   14   15
CONECT   15   27
END
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SMILES for HMDB0000929 (L-Tryptophan)

N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
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INCHI for HMDB0000929 (L-Tryptophan)

InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acidChEBI
(S)-alpha-Amino-1H-indole-3-propanoic acidChEBI
(S)-alpha-Amino-beta-(3-indolyl)-propionic acidChEBI
(S)-TryptophanChEBI
L-(-)-TryptophanChEBI
L-beta-3-IndolylalanineChEBI
TrpChEBI
TryptophanChEBI
WChEBI
(2S)-2-Amino-3-(1H-indol-3-yl)propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoic acidGenerator
(S)-alpha-Amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoic acidGenerator
(S)-a-Amino-b-(3-indolyl)-propionateGenerator
(S)-a-Amino-b-(3-indolyl)-propionic acidGenerator
(S)-alpha-Amino-beta-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionic acidGenerator
L-b-3-IndolylalanineGenerator
L-Β-3-indolylalanineGenerator
(-)-TryptophanHMDB
(L)-TryptophanHMDB
(S)-1H-Indole-3-alanineHMDB
(S)-2-Amino-3-(3-indolyl)propionic acidHMDB
(S)-a-Amino-b-indolepropionateHMDB
(S)-a-Amino-b-indolepropionic acidHMDB
(S)-a-Aminoindole-3-propionateHMDB
(S)-a-Aminoindole-3-propionic acidHMDB
(S)-alpha-Amino-beta-indolepropionateHMDB
(S)-alpha-Amino-beta-indolepropionic acidHMDB
(S)-alpha-Aminoindole-3-propionateHMDB
(S)-alpha-Aminoindole-3-propionic acidHMDB
1-beta-3-IndolylalanineHMDB
1beta-3-IndolylalanineHMDB
1H-Indole-3-alanineHMDB
2-Amino-3-indolylpropanoateHMDB
2-Amino-3-indolylpropanoic acidHMDB
3-(1H-indol-3-yl)-L-AlanineHMDB
3-indol-3-YlalanineHMDB
Alpha'-amino-3-indolepropionic acidHMDB
alpha-Aminoindole-3-propionic acidHMDB
ArdeytropinHMDB
H-TRP-OHHMDB
Indole-3-alanineHMDB
KalmaHMDB
L-alpha-Amino-3-indolepropionic acidHMDB
L-alpha-Aminoindole-3-propionic acidHMDB
L-TryptofanHMDB
L-TryptophaneHMDB
Lopac-T-0254HMDB
LyphanHMDB
OptimaxHMDB
PacitronHMDB
SedanoctHMDB
TriptofanoHMDB
TrofanHMDB
TryptacinHMDB
TryptanHMDB
TryptophaneHMDB
TryptophanumHMDB
ArdeydormHMDB
L TryptophanHMDB
L-Tryptophan-ratiopharmHMDB
Merck brand OF tryptophanHMDB
Niddapharm brand OF tryptophanHMDB
ICN brand OF tryptophanHMDB
LevotryptophanHMDB
PMS TryptophanHMDB
PMS-TryptophanHMDB
Ratiopharm brand OF tryptophanHMDB
Esparma brand OF tryptophanHMDB
Ratio-tryptophanHMDB
L Tryptophan ratiopharmHMDB
NaturruheHMDB
Tryptophan metabolism alterationsHMDB
Ardeypharm brand OF tryptophanHMDB
Kalma brand OF tryptophanHMDB
Pharmascience brand OF tryptophanHMDB
Upsher-smith brand OF tryptophanHMDB
Ratio tryptophanHMDB
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Traditional NameL-tryptophan
CAS Registry Number73-22-3
SMILES
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
InChI Identifier
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
InChI KeyQIVBCDIJIAJPQS-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationIndirect biological roleBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point230 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13.4 mg/mL at 25 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP-1.06HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker158.58130932474
[M-H]-Astarita_neg146.330932474
[M+H]+Astarita_pos145.030932474
[M+H]+Baker154.22530932474
[M-H]-Not Available158.581http://allccs.zhulab.cn/database/detail?ID=AllCCS00001785
[M+H]+Not Available152.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00001785
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP-1.1ALOGPS
logP-1.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m³·mol⁻¹ChemAxon
Polarizability21.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+147.62331661259
DarkChem[M-H]-146.23231661259
AllCCS[M+H]+146.28432859911
AllCCS[M-H]-146.6632859911
DeepCCS[M+H]+143.14830932474
DeepCCS[M-H]-140.75230932474
DeepCCS[M-2H]-174.60730932474
DeepCCS[M+Na]+149.28630932474
AllCCS[M+H]+146.332859911
AllCCS[M+H-H2O]+142.232859911
AllCCS[M+NH4]+150.132859911
AllCCS[M+Na]+151.232859911
AllCCS[M-H]-146.732859911
AllCCS[M+Na-2H]-146.832859911
AllCCS[M+HCOO]-147.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-TryptophanN[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O3444.1Standard polar33892256
L-TryptophanN[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O1998.1Standard non polar33892256
L-TryptophanN[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O2307.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Tryptophan,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=CC=C122197.3Semi standard non polar33892256
L-Tryptophan,1TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O2255.2Semi standard non polar33892256
L-Tryptophan,1TMS,isomer #3C[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC=CC=C212272.6Semi standard non polar33892256
L-Tryptophan,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C2210.1Semi standard non polar33892256
L-Tryptophan,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C2179.7Standard non polar33892256
L-Tryptophan,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C2633.2Standard polar33892256
L-Tryptophan,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C122225.1Semi standard non polar33892256
L-Tryptophan,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C122195.8Standard non polar33892256
L-Tryptophan,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C)C2=CC=CC=C122721.9Standard polar33892256
L-Tryptophan,2TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C2414.6Semi standard non polar33892256
L-Tryptophan,2TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C2259.1Standard non polar33892256
L-Tryptophan,2TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C2831.1Standard polar33892256
L-Tryptophan,2TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O2278.7Semi standard non polar33892256
L-Tryptophan,2TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O2218.2Standard non polar33892256
L-Tryptophan,2TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O2736.2Standard polar33892256
L-Tryptophan,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C2411.1Semi standard non polar33892256
L-Tryptophan,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C2329.2Standard non polar33892256
L-Tryptophan,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C2530.5Standard polar33892256
L-Tryptophan,3TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C2249.5Semi standard non polar33892256
L-Tryptophan,3TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C2250.8Standard non polar33892256
L-Tryptophan,3TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C2472.1Standard polar33892256
L-Tryptophan,3TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C2443.5Semi standard non polar33892256
L-Tryptophan,3TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C2353.1Standard non polar33892256
L-Tryptophan,3TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C2606.2Standard polar33892256
L-Tryptophan,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C2469.8Semi standard non polar33892256
L-Tryptophan,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C2388.7Standard non polar33892256
L-Tryptophan,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C2421.3Standard polar33892256
L-Tryptophan,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=C[NH]C2=CC=CC=C122475.2Semi standard non polar33892256
L-Tryptophan,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O2522.1Semi standard non polar33892256
L-Tryptophan,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(C[C@H](N)C(=O)O)C2=CC=CC=C212534.0Semi standard non polar33892256
L-Tryptophan,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C2710.2Semi standard non polar33892256
L-Tryptophan,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C2627.5Standard non polar33892256
L-Tryptophan,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C2814.8Standard polar33892256
L-Tryptophan,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122688.6Semi standard non polar33892256
L-Tryptophan,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122620.7Standard non polar33892256
L-Tryptophan,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122859.2Standard polar33892256
L-Tryptophan,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C2907.0Semi standard non polar33892256
L-Tryptophan,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C2700.5Standard non polar33892256
L-Tryptophan,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=C[NH]C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C2902.6Standard polar33892256
L-Tryptophan,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O2750.2Semi standard non polar33892256
L-Tryptophan,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O2650.4Standard non polar33892256
L-Tryptophan,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O2880.6Standard polar33892256
L-Tryptophan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3104.4Semi standard non polar33892256
L-Tryptophan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2971.5Standard non polar33892256
L-Tryptophan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=C[NH]C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2818.8Standard polar33892256
L-Tryptophan,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C2870.3Semi standard non polar33892256
L-Tryptophan,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C2877.8Standard non polar33892256
L-Tryptophan,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O[Si](C)(C)C(C)(C)C2789.6Standard polar33892256
L-Tryptophan,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C3094.8Semi standard non polar33892256
L-Tryptophan,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C2954.5Standard non polar33892256
L-Tryptophan,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O)[Si](C)(C)C(C)(C)C2853.8Standard polar33892256
L-Tryptophan,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3278.2Semi standard non polar33892256
L-Tryptophan,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3154.7Standard non polar33892256
L-Tryptophan,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2786.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0190000000-feaec8547634dddcad8c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0390000000-45a6c4fd79081597d44a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-9270000000-9761607cbe821f87f1722014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-MS (1 TMS)splash10-001i-0900000000-3faeed7ad32e1755c03c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-MS (3 TMS)splash10-0udi-0290000000-9c57a732e337fade3cb62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan EI-B (Non-derivatized)splash10-001i-0900000000-d054a214c1717940989f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan EI-B (Non-derivatized)splash10-0udi-0290000000-9860799c854e5c9ac1c72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)splash10-0udi-0190000000-feaec8547634dddcad8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)splash10-0udi-0390000000-45a6c4fd79081597d44a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-QQ (Non-derivatized)splash10-0udi-3729000000-86129db57aaf1a245f932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-EI-TOF (Non-derivatized)splash10-0fk9-9270000000-9761607cbe821f87f1722017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized)splash10-001i-0900000000-3faeed7ad32e1755c03c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized)splash10-0udi-0290000000-9c57a732e337fade3cb62017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b72016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9560000000-6829a8b2a2096883999f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Tryptophan GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0udi-0290602010-c09c931538bff74ac4002012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0a4i-0900000000-0fed327c2a56f556e04c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0udi-0090000000-98ec1c2c012e58eab9242012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00di-0090000000-fc77784da5d9b288d7512012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0udi-0290601010-d6f94902c0cf639cb7bc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0a4i-0900000000-27633a4f7ecfac45c7302012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0udi-0090000000-ee6cb8392b2e8d644bc12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0090000000-d81c86eceee1c9824b022012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0udi-0190000000-0e8b883dc8ab06c89d772012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0uxu-2940000000-cb35b9680612e19d8b3a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-014i-2900000000-7cc592351cc616b1d75f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-014i-1900000000-987615a0add5eb2c31692012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-014i-1900000000-f150d9d1e19c72d337a82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0uxr-2960000000-f4c878f3abb1609bb5c52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOFsplash10-0udi-0090000000-c73c9b49139319c80b182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOFsplash10-0gb9-0930000000-da94834297fcc5b3d3c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-94061fd1f6b08445cdf32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-e78172f4f27df232466e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-93406e2cdb79770abc7d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOFsplash10-0udi-0190000000-0e8b883dc8ab06c89d772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOFsplash10-0uxu-2940000000-cb35b9680612e19d8b3a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOFsplash10-014i-2900000000-5187dac98dbd6834d6ba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOFsplash10-014i-1900000000-987615a0add5eb2c31692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-QQ , negative-QTOFsplash10-014i-1900000000-174bb4d4390c75ae9a092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Tryptophan LC-ESI-ITFT , negative-QTOFsplash10-0a4i-0900000000-0fed327c2a56f556e04c2017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Fibroblasts
  • Neuron
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified54.5 +/- 9.7 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified78.4 +/- 15.5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified18-55 uMNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified25-80 uMInfant (1 - 3 months old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified21-80 uMChildren (3 months - 6 years old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified25-70 uMChildren (6 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified44.0 (37.0-51.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified81.3 +/- 3.36 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified87.4 (75.6-98.6) uMNewborn (0-30 days old)Not Available
Normal		 details
BloodDetected and Quantified48.7 +/- 11.6 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified101.5 +/- 27.2 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified45.0 +/- 9.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified73.9 (63-87) uMInfant (0-1 year old)Not Available
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified69.71 +/- 0.99 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified63.0 +/- 10.7 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified36.5(20.6-51.8) uMChildren (1-13 uears old)Both
Normal		 details
BloodDetected and Quantified40.0-95.0 uMAdult (>18 years old)Both
Normal		 details
Breast MilkDetected and Quantified3.2 +/- 1.3 uMAdult (>18 years old)Female
Normal		 details
Cerebrospinal Fluid (CSF)Detected and Quantified5 +/- 3 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.3 +/- 0.4 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.96 +/- 8.83 uMChildren (1 - 13 years old)FemaleNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified1.18 +/- 1.15 uMChildren (1 - 13 years old)MaleNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified2.32 +/- 0.09 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.25 +/- 0.95 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified20.4 +/- 8.2 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 +/- 0.53 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 (1.2-2.5) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified15.9 +/- 4.1 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.64 +/- 0.52 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.5-8 uMChildren (0 - 10 years old)Both
Normal
    • BC Children's Hos...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.5-9 uMAdolescent (>11 years old)Both
Normal
    • BC Children's Hos...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified2.3 uMChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected and Quantified170 +/- 110 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not SpecifiedNormal details
FecesDetected and Quantified20 +/- 20 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal		 details
SalivaDetected and Quantified0.5 +/- 0.5 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.46 +/- 0.31 uMAdult (>18 years old)FemaleNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified4.80 +/- 3.41 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SweatDetected and Quantified< 10 uMAdult (60 years old)Male
Normal		 details
SweatDetected and Quantified< 10 uMAdult (40 years old)Male
Normal		 details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected and Quantified2.04 - 21.03 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified4.97 - 46.02 umol/mmol creatinineInfant (1 - 6 months old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified4.97 - 46.02 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified4.97 - 46.02 umol/mmol creatinineChildren (1 - 2 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified2.04 - 27.02 umol/mmol creatinineChildren (2 - 4 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified2.04 - 27.02 umol/mmol creatinineChildren (4 - 13 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified2.04 - 27.02 umol/mmol creatinineAdolescent (13 - 21 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified2.04 - 14.02 umol/mmol creatinineAdult (>21 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified1.13-34.27 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified20.35 +/- 22.61 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified23.74 +/- 31.66 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified26.00 +/- 32.79 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified7.8 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.70-25.90 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified7.377 (3.917-12.274) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.45-29.40 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
 details
UrineDetected and Quantified13.52 +/- 7.37 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified1.86-6.03 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified3.22 +/- 0.97 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified3.44 +/- 0.99 umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified3.6-6.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified2.036-12.90 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.62 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Shaykhutdinov RA,...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified1.58-35.63 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified11.931 +/- 6.642 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.21-72.48 umol/mmol creatinineNewborn (0-30 days old)Female
Normal		 details
UrineDetected and Quantified0.45-15.92 umol/mmol creatinineNewborn (0-30 days old)Male
Normal		 details
UrineDetected and Quantified11.48 +/- 16.66 umol/mmol creatinineNewborn (0-30 days old)Female
Normal		 details
UrineDetected and Quantified4.0 +/- 3.9 umol/mmol creatinineNewborn (0-30 days old)Male
Normal		 details
UrineDetected and Quantified9.57 +/- 7.27 umol/mmol creatinineChildren (0-2 years old)Male
Normal		 details
UrineDetected and Quantified9.85 +/- 6.69 umol/mmol creatinineChildren (0-2 years old)Female
Normal		 details
UrineDetected and Quantified5.6 (2.1-9.3) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified1.58-35.63 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified3.82 (2.59-6.49) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
UrineDetected and Quantified6.3 (3.4-11.1) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified10-40 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified4.4-6.9 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.9 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.263 (1.316-9.211) umol/mmol creatinineAdult (>18 years old)BothNormal
      Not Available
 details
UrineDetected and Quantified1.13-34.27 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia		 details
BloodDetected and Quantified63.6 uMInfant (0-1 year old)FemaleNicotinamide Adenine Dinucleotide Deficiency details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Ovarian cancer		 details
BloodDetected and Quantified83.3 +/- 26.0 uMAdult (>18 years old)MaleSchizophrenia details
BloodDetected and Quantified80.2 +/- 22.0 uMAdult (>18 years old)FemaleSchizophrenia details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Oesophageal cancer		 details
BloodDetected and Quantified76.2 +/- 15.4 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
 details
BloodDetected and Quantified84.6 +/- 16.7 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
 details
BloodDetected and Quantified31.6 (29.6-33.6) uMAdult (>18 years old)Both
Epilepsy		 details
BloodDetected and Quantified37.2 (34.3-40.1) uMAdult (>18 years old)Both
Epilepsy		 details
BloodDetected and Quantified53.3 (50.3-56.3) uMAdult (>18 years old)Both
Epilepsy		 details
BloodDetected and Quantified27.2(8.3-35) uMAdult (>18 years old)BothSepsis details
BloodDetected and Quantified101 +/- 4.48 uMAdult (>18 years old)Both
Schizophrenia		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
BloodDetected and Quantified63.51 +/- 2.04 uMAdult (>18 years old)Both
Schizophrenia		 details
BloodDetected and Quantified33.06 +/- 8.99 uMAdult (>18 years old)BothAlzheimer's disease details
BloodDetected and Quantified36.7(25.2-50.8) uMChildren (1-13 uears old)Both
Environmental enteric dysfunction		 details
Cerebrospinal Fluid (CSF)Detected and Quantified2.035 +/- 0.649 uMAdult (>18 years old)Not Specifiedceliac disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0018 +/- 0.0003 uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified1.6 +/- 0.3 uMAdult (>18 years old)BothHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified1.0 +/- 0.2 uMChildren (1-13 years old)BothHartnup Disease details
Cerebrospinal Fluid (CSF)Detected and Quantified1.7 +/- 0.27 uMAdult (>18 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified1.6+/- 0.57 uMAdult (>18 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified1.7 +/- 0.4 uMAdult (>18 years old)Not SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified1.68 +/- 0.52 uMAdult (>18 years old)BothEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified14.3 +/- 12.5 uMAdult (>18 years old)Not SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified11.5 +/- 8.2 uMAdult (>18 years old)Not SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified13.0 +/- 5.2 uMChildren (1-13 years old)Not SpecifiedLeukemia details
Cerebrospinal Fluid (CSF)Detected and Quantified12.8 +/- 3.5 uMChildren (1-13 years old)Not Specified
Leukemia		 details
Cerebrospinal Fluid (CSF)Detected and Quantified2.42 +/- 0.14 uMAdult (>18 years old)Not SpecifiedOlivopontocerebellar atrophy (OPCA) details
Cerebrospinal Fluid (CSF)Detected and Quantified1.80 +/- 0.2 uMAdult (>18 years old)Not SpecifiedAutosomal recessive spastic ataxia of Charlevoix-Saguena details
Cerebrospinal Fluid (CSF)Detected and Quantified1.8 +/- 0.3 uMAdult (>18 years old)Not SpecifiedHypothyroidism details
Cerebrospinal Fluid (CSF)Detected and Quantified1.3 +/- 0.32 uMAdult (>18 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified2.4 +/- 0.13 uMNot SpecifiedNot SpecifiedFriedreich's ataxia details
Cerebrospinal Fluid (CSF)Detected and Quantified2.67 +/- 0.6 uMAdult (>18 years old)BothSchizophrenia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCCD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothIleal Crohn's disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Bothceliac disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Femaleankylosing spondylitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Femalerheumatoid arthritis details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specifiedceliac disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease		 details
SalivaDetected and Quantified0.22 +/- 0.16 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPeriodontal diseases details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected and Quantified0.40 +/- 0.21 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected and Quantified0.60 +/- 0.49 uMAdult (>18 years old)BothLewy body disease details
UrineDetected and Quantified10.707-21.382 umol/mmol creatinineChildren (1-13 years old)FemaleTryptophanuria with dwarfism details
UrineDetected and Quantified7.83 +/- 7.48 umol/mmol creatinineAdult (>18 years old)BothCachexia details
UrineDetected and Quantified12.011 +/- 6.328 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.19 +/- 0.23 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease References
Epilepsy
  1. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
  2. Botez MI, Young SN: Effects of anticonvulsant treatment and low levels of folate and thiamine on amine metabolites in cerebrospinal fluid. Brain. 1991 Feb;114 ( Pt 1A):333-48. [PubMed:1705463 ]
Schizophrenia
  1. Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. [PubMed:2480613 ]
  2. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
  3. Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
  4. Kim YK, Myint AM, Verkerk R, Scharpe S, Steinbusch H, Leonard B: Cytokine changes and tryptophan metabolites in medication-naive and medication-free schizophrenic patients. Neuropsychobiology. 2009;59(2):123-9. doi: 10.1159/000213565. Epub 2009 Apr 22. [PubMed:19390223 ]
  5. Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Alzheimer's disease
  1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
  2. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Colorectal cancer
  1. Qiu Y, Cai G, Su M, Chen T, Zheng X, Xu Y, Ni Y, Zhao A, Xu LX, Cai S, Jia W: Serum metabolite profiling of human colorectal cancer using GC-TOFMS and UPLC-QTOFMS. J Proteome Res. 2009 Oct;8(10):4844-50. doi: 10.1021/pr9004162. [PubMed:19678709 ]
  2. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  4. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  5. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ovarian cancer
  1. Zhang T, Wu X, Yin M, Fan L, Zhang H, Zhao F, Zhang W, Ke C, Zhang G, Hou Y, Zhou X, Lou G, Li K: Discrimination between malignant and benign ovarian tumors by plasma metabolomic profiling using ultra performance liquid chromatography/mass spectrometry. Clin Chim Acta. 2012 May 18;413(9-10):861-8. doi: 10.1016/j.cca.2012.01.026. Epub 2012 Jan 30. [PubMed:22309680 ]
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Nicotinamide Adenine Dinucleotide Deficiency
  1. Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]
Sepsis
  1. Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Hartnup disease
  1. Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. [PubMed:2472426 ]
Leukemia
  1. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
Olivopontocerebral atrophy
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hereditary spastic paraplegia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hypothyroidism
  1. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Friedreich's ataxia
  1. Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Celiac disease
  1. Hallert C, Allenmark S, Larsson-Cohn U, Sedvall G: High level of pyridoxal 5'-phosphate in the cerebrospinal fluid of adult celiac patients. Am J Clin Nutr. 1982 Nov;36(5):851-4. [PubMed:6182788 ]
  2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
  3. De Angelis M, Vannini L, Di Cagno R, Cavallo N, Minervini F, Francavilla R, Ercolini D, Gobbetti M: Salivary and fecal microbiota and metabolome of celiac children under gluten-free diet. Int J Food Microbiol. 2016 Dec 19;239:125-132. doi: 10.1016/j.ijfoodmicro.2016.07.025. Epub 2016 Jul 19. [PubMed:27452636 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  2. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Rheumatoid arthritis
  1. Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Cachexia
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Tryptophanuria with dwarfism
  1. TADA K, ITO H, WADA Y, ARAKAWA T: CONGENITAL TRYPTOPHANURIA WITH DWARFISM ("H" DISEASE-LIKE CLINICAL FEATURES WITHOUT INDICANURIA AND GENERALIZED AMINOACIDURIA):--A PROBABLY NEW INBORN ERROR OF TRYPTOPHAN METABOLISM. Tohoku J Exp Med. 1963 Jul 25;80:118-34. [PubMed:14055140 ]
Associated OMIM IDs
DrugBank IDDB00150
Phenol Explorer Compound IDNot Available
FooDB IDFDB002250
KNApSAcK IDC00001396
Chemspider ID6066
KEGG Compound IDC00078
BioCyc IDTRP
BiGG ID33772
Wikipedia LinkTryptophan
METLIN ID5879
PubChem Compound6305
PDB IDNot Available
ChEBI ID16828
Food Biomarker OntologyNot Available
VMH IDTRP_L
MarkerDB IDMDB00000284
Good Scents IDNot Available
References
Synthesis ReferenceAmir-Heidari, Bagher; Thirlway, Jenny; Micklefield, Jason. Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics. Organic Letters (2007), 9(8), 1513-1516.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
  3. Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
  4. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
  5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
  6. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
  7. Buczko W, Cylwik D, Stokowska W: [Metabolism of tryptophan via the kynurenine pathway in saliva]. Postepy Hig Med Dosw (Online). 2005;59:283-9. [PubMed:15995595 ]
  8. Heyes MP, Saito K, Crowley JS, Davis LE, Demitrack MA, Der M, Dilling LA, Elia J, Kruesi MJ, Lackner A, et al.: Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Brain. 1992 Oct;115 ( Pt 5):1249-73. [PubMed:1422788 ]
  9. Koskiniemi M, Laakso J, Kuurne T, Laipio M, Harkonen M: Indole levels in human lumbar and ventricular cerebrospinal fluid and the effect of L-tryptophan administration. Acta Neurol Scand. 1985 Feb;71(2):127-32. [PubMed:2580417 ]
  10. Jonas AJ, Butler IJ: Circumvention of defective neutral amino acid transport in Hartnup disease using tryptophan ethyl ester. J Clin Invest. 1989 Jul;84(1):200-4. [PubMed:2472426 ]
  11. Guchhait RB, Janson C, Price WH: Validity of plasma factor in schizophrenia as measured by tryptophan uptake. Biol Psychiatry. 1975 Jun;10(3):303-14. [PubMed:49200 ]
  12. Kennedy JS, Gwirtsman HE, Schmidt DE, Johnson BW, Fielstein E, Salomon RM, Shiavi RG, Ebert MH, Parris WC, Loosen PT: Serial cerebrospinal fluid tryptophan and 5-hydroxy indoleacetic acid concentrations in healthy human subjects. Life Sci. 2002 Aug 23;71(14):1703-15. [PubMed:12137916 ]
  13. Bender KI, Lutsevich NF, Lutsevich AN, Kupchikov VV: [Endogenous metabolites as modulators of the transport of drugs by serum albumin]. Farmakol Toksikol. 1990 May-Jun;53(3):72-80. [PubMed:2201566 ]
  14. Heiman-Patterson TD, Bird SJ, Parry GJ, Varga J, Shy ME, Culligan NW, Edelsohn L, Tatarian GT, Heyes MP, Garcia CA, et al.: Peripheral neuropathy associated with eosinophilia-myalgia syndrome. Ann Neurol. 1990 Oct;28(4):522-8. [PubMed:2174666 ]
  15. Talbert AM, Tranter GE, Holmes E, Francis PL: Determination of drug-plasma protein binding kinetics and equilibria by chromatographic profiling: exemplification of the method using L-tryptophan and albumin. Anal Chem. 2002 Jan 15;74(2):446-52. [PubMed:11811421 ]
  16. Dunner DL, Heiber S, Perel JM: The effect of L-tryptophan administration on the concentration of probenecid in plasma and cerebrospinal fluid in patients. Psychopharmacology (Berl). 1977 Aug 16;53(3):305-8. [PubMed:408860 ]
  17. George CF, Millar TW, Hanly PJ, Kryger MH: The effect of L-tryptophan on daytime sleep latency in normals: correlation with blood levels. Sleep. 1989 Aug;12(4):345-53. [PubMed:2669092 ]
  18. Gutsche B, Grun C, Scheutzow D, Herderich M: Tryptophan glycoconjugates in food and human urine. Biochem J. 1999 Oct 1;343 Pt 1:11-9. [PubMed:10493906 ]
  19. Milburn DS, Myers CW: Tryptophan toxicity: a pharmacoepidemiologic review of eosinophilia-myalgia syndrome. DICP. 1991 Nov;25(11):1259-62. [PubMed:1763543 ]
  20. Gross B, Ronen N, Honigman S, Livne E: Tryptophan toxicity--time and dose response in rats. Adv Exp Med Biol. 1999;467:507-16. [PubMed:10721094 ]
  21. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  22. Mehraj V, Routy JP: Tryptophan Catabolism in Chronic Viral Infections: Handling Uninvited Guests. Int J Tryptophan Res. 2015 Aug 4;8:41-8. doi: 10.4137/IJTR.S26862. eCollection 2015. [PubMed:26309411 ]
  23. Lionetto L, Ulivieri M, Capi M, De Bernardini D, Fazio F, Petrucca A, Pomes LM, De Luca O, Gentile G, Casolla B, Curto M, Salerno G, Schillizzi S, Torre MS, Santino I, Rocco M, Marchetti P, Aceti A, Ricci A, Bonfini R, Nicoletti F, Simmaco M, Borro M: Increased kynurenine-to-tryptophan ratio in the serum of patients infected with SARS-CoV2: An observational cohort study. Biochim Biophys Acta Mol Basis Dis. 2021 Mar 1;1867(3):166042. doi: 10.1016/j.bbadis.2020.166042. Epub 2020 Dec 16. [PubMed:33338598 ]
  24. Darcy CJ, Davis JS, Woodberry T, McNeil YR, Stephens DP, Yeo TW, Anstey NM: An observational cohort study of the kynurenine to tryptophan ratio in sepsis: association with impaired immune and microvascular function. PLoS One. 2011;6(6):e21185. doi: 10.1371/journal.pone.0021185. Epub 2011 Jun 22. [PubMed:21731667 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Aromatic-L-amino-acid decarboxylase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Reactions
L-Tryptophan → Tryptamine + Carbon dioxidedetails
References
  1. Tyce GM: Origin and metabolism of serotonin. J Cardiovasc Pharmacol. 1990;16 Suppl 3:S1-7. [PubMed:1369709 ]
Enzyme Details
2. Indoleamine 2,3-dioxygenase 1
General function:
Involved in heme binding
Specific function:
Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
Gene Name:
IDO1
Uniprot ID:
P14902
Molecular weight:
45325.89
Reactions
L-Tryptophan + Oxygen → L-Formylkynureninedetails
References
  1. Agaugue S, Perrin-Cocon L, Coutant F, Andre P, Lotteau V: 1-Methyl-tryptophan can interfere with TLR signaling in dendritic cells independently of IDO activity. J Immunol. 2006 Aug 15;177(4):2061-71. [PubMed:16887964 ]
  2. Fallarino F, Gizzi S, Mosci P, Grohmann U, Puccetti P: Tryptophan catabolism in IDO+ plasmacytoid dendritic cells. Curr Drug Metab. 2007 Apr;8(3):209-16. [PubMed:17430109 ]
  3. Cozzi A, Zignego AL, Carpendo R, Biagiotti T, Aldinucci A, Monti M, Giannini C, Rosselli M, Laffi G, Moroni F: Low serum tryptophan levels, reduced macrophage IDO activity and high frequency of psychopathology in HCV patients. J Viral Hepat. 2006 Jun;13(6):402-8. [PubMed:16842443 ]
  4. Grohmann U, Volpi C, Fallarino F, Bozza S, Bianchi R, Vacca C, Orabona C, Belladonna ML, Ayroldi E, Nocentini G, Boon L, Bistoni F, Fioretti MC, Romani L, Riccardi C, Puccetti P: Reverse signaling through GITR ligand enables dexamethasone to activate IDO in allergy. Nat Med. 2007 May;13(5):579-86. Epub 2007 Apr 8. [PubMed:17417651 ]
  5. Zheng X, Koropatnick J, Li M, Zhang X, Ling F, Ren X, Hao X, Sun H, Vladau C, Franek JA, Feng B, Urquhart BL, Zhong R, Freeman DJ, Garcia B, Min WP: Reinstalling antitumor immunity by inhibiting tumor-derived immunosuppressive molecule IDO through RNA interference. J Immunol. 2006 Oct 15;177(8):5639-46. [PubMed:17015752 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. doi: 10.1042/BST0370408. [PubMed:19290871 ]
Enzyme Details
3. Tryptophan 5-hydroxylase 1
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH1
Uniprot ID:
P17752
Molecular weight:
50984.725
Reactions
L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterindetails
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
References
  1. Pavon JA, Fitzpatrick PF: Insights into the catalytic mechanisms of phenylalanine and tryptophan hydroxylase from kinetic isotope effects on aromatic hydroxylation. Biochemistry. 2006 Sep 12;45(36):11030-7. [PubMed:16953590 ]
  2. Langfort J, Baranczuk E, Pawlak D, Chalimoniuk M, Lukacova N, Marsala J, Gorski J: The effect of endurance training on regional serotonin metabolism in the brain during early stage of detraining period in the female rat. Cell Mol Neurobiol. 2006 Oct-Nov;26(7-8):1327-42. Epub 2006 Aug 1. [PubMed:16897368 ]
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [PubMed:17519505 ]
  4. Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. [PubMed:17492791 ]
  5. Neckameyer WS, Coleman CM, Eadie S, Goodwin SF: Compartmentalization of neuronal and peripheral serotonin synthesis in Drosophila melanogaster. Genes Brain Behav. 2007 Nov;6(8):756-69. Epub 2007 Mar 21. [PubMed:17376153 ]
Enzyme Details
4. Tryptophan 5-hydroxylase 2
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
TPH2
Uniprot ID:
Q8IWU9
Molecular weight:
56056.295
Reactions
L-Tryptophan + Tetrahydrobiopterin + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Hydroxytetrahydrobiopterindetails
Tetrahydrobiopterin + L-Tryptophan + Oxygen → 5-Hydroxy-L-tryptophan + 4a-Carbinolamine tetrahydrobiopterin + Waterdetails
References
  1. Lopez VA, Detera-Wadleigh S, Cardona I, Kassem L, McMahon FJ: Nested association between genetic variation in tryptophan hydroxylase II, bipolar affective disorder, and suicide attempts. Biol Psychiatry. 2007 Jan 15;61(2):181-6. Epub 2006 Jun 27. [PubMed:16806105 ]
  2. Kraus MR, Al-Taie O, Schafer A, Pfersdorff M, Lesch KP, Scheurlen M: Serotonin-1A receptor gene HTR1A variation predicts interferon-induced depression in chronic hepatitis C. Gastroenterology. 2007 Apr;132(4):1279-86. Epub 2007 Feb 25. [PubMed:17408646 ]
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [PubMed:17519505 ]
  4. Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. [PubMed:17492791 ]
  5. Calcagno E, Canetta A, Guzzetti S, Cervo L, Invernizzi RW: Strain differences in basal and post-citalopram extracellular 5-HT in the mouse medial prefrontal cortex and dorsal hippocampus: relation with tryptophan hydroxylase-2 activity. J Neurochem. 2007 Nov;103(3):1111-20. Epub 2007 Jul 31. [PubMed:17666043 ]
Enzyme Details
5. Tryptophan--tRNA ligase, cytoplasmic
General function:
Involved in nucleotide binding
Specific function:
Isoform 1, isoform 2 and T1-TrpRS have aminoacylation activity while T2-TrpRS lacks it. Isoform 2, T1-TrpRS and T2-TrpRS possess angiostatic activity whereas isoform 1 lacks it. T2-TrpRS inhibits fluid shear stress-activated responses of endothelial cells. Regulates ERK, Akt, and eNOS activation pathways that are associated with angiogenesis, cytoskeletal reorganization and shear stress-responsive gene expression.
Gene Name:
WARS
Uniprot ID:
P23381
Molecular weight:
53164.91
Reactions
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)details
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)details
References
  1. Tsuchiya W, Umehara T, Kuno A, Hasegawa T: Determination of tryptophan tRNA recognition sites for tryptophanyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2004;(48):185-6. [PubMed:17150540 ]
  2. Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [PubMed:17428498 ]
  3. Zhu L, Ji F, Wang Y, Zhang Y, Liu Q, Zhang JZ, Matsushima K, Cao Q, Zhang Y: Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. J Immunol. 2006 Dec 1;177(11):8226-33. [PubMed:17114500 ]
  4. Yadav MC, Burudi EM, Alirezaei M, Flynn CC, Watry DD, Lanigan CM, Fox HS: IFN-gamma-induced IDO and WRS expression in microglia is differentially regulated by IL-4. Glia. 2007 Oct;55(13):1385-96. [PubMed:17661345 ]
  5. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [PubMed:16724112 ]
Enzyme Details
6. Tryptophan--tRNA ligase, mitochondrial
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
WARS2
Uniprot ID:
Q9UGM6
Molecular weight:
40146.265
Reactions
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-tryptophyl-tRNA(Trp)details
Adenosine triphosphate + L-Tryptophan + tRNA(Trp) → Adenosine monophosphate + Pyrophosphate + L-Tryptophanyl-tRNA(Trp)details
References
  1. Paley EL, Denisova G, Sokolova O, Posternak N, Wang X, Brownell AL: Tryptamine induces tryptophanyl-tRNA synthetase-mediated neurodegeneration with neurofibrillary tangles in human cell and mouse models. Neuromolecular Med. 2007;9(1):55-82. [PubMed:17114825 ]
  2. Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [PubMed:17428498 ]
  3. Banin E, Dorrell MI, Aguilar E, Ritter MR, Aderman CM, Smith AC, Friedlander J, Friedlander M: T2-TrpRS inhibits preretinal neovascularization and enhances physiological vascular regrowth in OIR as assessed by a new method of quantification. Invest Ophthalmol Vis Sci. 2006 May;47(5):2125-34. [PubMed:16639024 ]
  4. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [PubMed:16724112 ]
  5. Charriere F, Helgadottir S, Horn EK, Soll D, Schneider A: Dual targeting of a single tRNA(Trp) requires two different tryptophanyl-tRNA synthetases in Trypanosoma brucei. Proc Natl Acad Sci U S A. 2006 May 2;103(18):6847-52. Epub 2006 Apr 24. [PubMed:16636268 ]
Enzyme Details
7. Tryptophan 2,3-dioxygenase
General function:
Involved in tryptophan 2,3-dioxygenase activity
Specific function:
Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
Gene Name:
TDO2
Uniprot ID:
P48775
Molecular weight:
47871.215
Reactions
L-Tryptophan + Oxygen → L-Formylkynureninedetails
References
  1. Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. doi: 10.1042/BST0370408. [PubMed:19290871 ]
Enzyme Details
8. Indoleamine 2,3-dioxygenase 2
General function:
Involved in heme binding
Specific function:
Catalyzes the first and rate-limiting step in the kynurenine pathway of tryptophan catabolism.
Gene Name:
IDO2
Uniprot ID:
Q6ZQW0
Molecular weight:
47074.745
Reactions
L-Tryptophan + Oxygen → L-Formylkynureninedetails
Enzyme Details
9. L-amino-acid oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:
IL4I1
Uniprot ID:
Q96RQ9
Molecular weight:
65327.26
Reactions
L-Tryptophan + Water + Oxygen → Indolepyruvate + Ammonia + Hydrogen peroxidedetails

Transporters

Enzyme Details
1. Monocarboxylate transporter 8
General function:
Involved in transmembrane transport
Specific function:
Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu, Phe, Trp or Tyr
Gene Name:
SLC16A2
Uniprot ID:
P36021
Molecular weight:
59510.9
References
  1. Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. [PubMed:12871948 ]
Enzyme Details
2. Monocarboxylate transporter 10
General function:
Involved in transmembrane transport
Specific function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1
References
  1. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462 ]
  2. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters