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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (2) Show 11 proteins XML

enzymes (9)transporters (2) Show 11 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014339

Secondary Accession Numbers

HMDB14339

Metabolite Identification

Common Name

Tramadol

Description

Tramadol is only found in individuals that have used or taken this drug. It is a narcotic analgesic proposed for moderate to severe pain. It may be habituating (PubChem). Tramadol and its O-desmethyl metabolite (M1) are selective, weak OP3-receptor agonists. Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. As the effector system is adenylate cyclase and cAMP is located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. The analgesic properties of tramadol can be attributed to norepinephrine and serotonin reuptake blockade in the CNS, which inhibits pain transmission in the spinal cord. The (+) enantiomer has a higher affinity for the OP3 receptor and preferentially inhibits serotonin uptake and enhances serotonin release. The (-) enantiomer preferentially inhibits norepinephrine reuptake by stimulating alpha(2)-adrenergic receptors.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014339
     RDKit          3D
Tramadol
 44 45  0  0  0  0  0  0  0  0999 V2000
    5.0034    2.5250   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299    1.9046   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.9399   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.4675    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340   -0.5057    1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786   -1.0170    1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108   -0.5637    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037   -1.1117   -0.5888 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0695   -0.8775   -1.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -2.6223   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -3.1229    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -2.7332   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549   -1.2609   -0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843   -0.5450   -0.0185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3181    0.9332   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682    1.6167    0.3619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589    1.5350   -0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576    2.9975    0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676    0.4077   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2131    2.4021    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    3.6481   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8886    2.1071   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    0.8511    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785   -0.8696    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947   -1.7842    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9854   -1.0376   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.9368   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -3.1480   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0510   -2.8556    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0530   -4.2495    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392   -3.0491    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -3.3387   -1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -0.8903   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5899   -1.1672   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2478   -0.8809    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4470    1.3096    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.2792   -1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535    2.5680   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871    1.0198   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5177    1.1262    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0330    3.6223   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094    3.4389    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    3.0788    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203    0.7886   -1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  7 19  2  0
 19  3  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
M  END


  Mrv1652305091822472D          

 19 20  0  0  0  0            999 V2000
10005.128310004.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.700910005.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.986010006.1502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.267110005.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.986010006.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.274310004.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.990310004.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.699510004.9117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.985010004.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.985010003.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.699510003.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.413910003.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.413910004.4992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10005.842910006.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.128610005.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.128610004.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.842910004.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.557310004.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.557310005.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8  2  1  6  0  0  0
 13  1  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 18  6  1  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014339

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3/t14-,16+/m1/s1

> <INCHI_KEY>
TVYLLZQTGLZFBW-ZBFHGGJFSA-N

> <FORMULA>
C16H25NO2

> <MOLECULAR_WEIGHT>
263.3752

> <EXACT_MASS>
263.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.452983864104386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.4498614993333323

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.79521779464169

> <JCHEM_PKA_STRONGEST_BASIC>
9.231111081713522

> <JCHEM_POLAR_SURFACE_AREA>
32.7

> <JCHEM_REFRACTIVITY>
78.26920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tramadol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014339
     RDKit          3D
Tramadol
 44 45  0  0  0  0  0  0  0  0999 V2000
    5.0034    2.5250   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299    1.9046   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.9399   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.4675    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340   -0.5057    1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786   -1.0170    1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108   -0.5637    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037   -1.1117   -0.5888 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0695   -0.8775   -1.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -2.6223   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -3.1229    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -2.7332   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549   -1.2609   -0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843   -0.5450   -0.0185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3181    0.9332   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682    1.6167    0.3619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589    1.5350   -0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576    2.9975    0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676    0.4077   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2131    2.4021    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    3.6481   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8886    2.1071   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    0.8511    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785   -0.8696    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947   -1.7842    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9854   -1.0376   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.9368   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -3.1480   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0510   -2.8556    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0530   -4.2495    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392   -3.0491    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -3.3387   -1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -0.8903   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5899   -1.1672   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2478   -0.8809    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4470    1.3096    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.2792   -1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535    2.5680   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871    1.0198   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5177    1.1262    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0330    3.6223   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094    3.4389    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    3.0788    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203    0.7886   -1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  7 19  2  0
 19  3  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 09-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-18         0                                  
HETATM    1  O   UNK     0    8676.2398674.296   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8673.5758677.377   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8672.2418678.147   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8670.8998677.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8672.2418679.688   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8680.2458675.065   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8681.5828675.837   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8673.5728675.835   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.2398675.065   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.2398673.525   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8673.5728672.755   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8674.9068673.525   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8674.9068675.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8677.5738678.147   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8676.2408677.376   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8676.2408675.836   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8677.5738675.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8678.9078675.836   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8678.9078677.376   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2    3    8                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   18                                                       
CONECT    7    6                                                            
CONECT    8    9   13    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    8   12    1   16                                             
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   13                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19    6                                                  
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014339
HETATM    1  C1  UNL     1       5.003   2.525  -0.292  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.830   1.905  -0.706  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.150   0.940  -0.016  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.576   0.467   1.200  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.834  -0.506   1.829  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.679  -1.017   1.277  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.211  -0.564   0.040  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.004  -1.112  -0.589  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.070  -0.877  -1.981  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.012  -2.622  -0.434  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.105  -3.123   0.425  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.395  -2.733  -0.260  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.455  -1.261  -0.594  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.284  -0.545  -0.019  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.318   0.933  -0.104  1.00  0.00           C  
HETATM   16  N1  UNL     1      -2.468   1.617   0.362  1.00  0.00           N  
HETATM   17  C14 UNL     1      -3.659   1.535  -0.398  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.158   2.998   0.647  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.968   0.408  -0.572  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.213   2.402   0.786  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.953   3.648  -0.458  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.889   2.107  -0.860  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.494   0.851   1.671  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.178  -0.870   2.784  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.095  -1.784   1.776  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.985  -1.038  -2.250  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.029  -2.937  -0.056  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.088  -3.148  -1.429  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.051  -2.856   1.479  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.053  -4.249   0.353  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.239  -3.049   0.420  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.448  -3.339  -1.183  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.370  -0.890  -0.070  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.590  -1.167  -1.667  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.248  -0.881   1.077  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.447   1.310   0.527  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.012   1.279  -1.137  1.00  0.00           H  
HETATM   38  H19 UNL     1      -4.054   2.568  -0.699  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.587   1.020  -1.370  1.00  0.00           H  
HETATM   40  H21 UNL     1      -4.518   1.126   0.193  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.033   3.622  -0.254  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.009   3.439   1.214  1.00  0.00           H  
HETATM   43  H24 UNL     1      -1.202   3.079   1.215  1.00  0.00           H  
HETATM   44  H25 UNL     1       1.620   0.789  -1.524  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   25
CONECT    7    8   19   19
CONECT    8    9   10   14
CONECT    9   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   15   35
CONECT   15   16   36   37
CONECT   16   17   18
CONECT   17   38   39   40
CONECT   18   41   42   43
CONECT   19   44
END

HMDB0014339
     RDKit          3D
Tramadol
 44 45  0  0  0  0  0  0  0  0999 V2000
    5.0034    2.5250   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299    1.9046   -0.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.9399   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5763    0.4675    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340   -0.5057    1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786   -1.0170    1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108   -0.5637    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037   -1.1117   -0.5888 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0695   -0.8775   -1.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -2.6223   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -3.1229    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953   -2.7332   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549   -1.2609   -0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843   -0.5450   -0.0185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3181    0.9332   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682    1.6167    0.3619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589    1.5350   -0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576    2.9975    0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676    0.4077   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2131    2.4021    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    3.6481   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8886    2.1071   -0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    0.8511    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785   -0.8696    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947   -1.7842    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9854   -1.0376   -2.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.9368   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -3.1480   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0510   -2.8556    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0530   -4.2495    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2392   -3.0491    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -3.3387   -1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -0.8903   -0.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5899   -1.1672   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2478   -0.8809    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4470    1.3096    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    1.2792   -1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535    2.5680   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871    1.0198   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5177    1.1262    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0330    3.6223   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0094    3.4389    1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    3.0788    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203    0.7886   -1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  7 19  2  0
 19  3  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Tramadol	ChEBI
(+)-trans-2-(Dimethylaminomethyl)-1-(m-methoxyphenyl)cyclohexanol	ChEBI
Amanda	Kegg
1a Brand OF tramadol hydrochloride	HMDB
ASTA medica brand OF tramadol hydrochloride	HMDB
AbZ brand OF tramadol hydrochloride	HMDB
Adolonta	HMDB
Bayvit brand OF tramadol hydrochloride	HMDB
Bexal brand OF tramadol hydrochloride	HMDB
Dolorgiet brand OF tramadol hydrochloride	HMDB
Edigen brand OF tramadol hydrochloride	HMDB
Hexal brand OF tramadol hydrochloride	HMDB
Lindopharm brand OF tramadol hydrochloride	HMDB
MTW Brand OF tramadol hydrochloride	HMDB
MTW Tramadol	HMDB
Mabo brand OF tramadol hydrochloride	HMDB
Q-Pharm brand OF tramadol hydrochloride	HMDB
Rowa brand OF tramadol hydrochloride	HMDB
Theraplix brand OF tramadol hydrochloride	HMDB
Tradol-puren	HMDB
TradolPuren	HMDB
Trama 1a pharma	HMDB
Trama KD	HMDB
Tramadol asta medica	HMDB
Tramadol bexal	HMDB
Tramadol edigen	HMDB
Tramadol ratiopharm	HMDB
TramadolHameln	HMDB
Ultram	HMDB
Zydol	HMDB
Alpharma brand OF tramadol hydrochloride	HMDB
Biodalgic	HMDB
Byk brand OF tramadol hydrochloride	HMDB
Ciclum brand OF tramadol hydrochloride	HMDB
Cinfa brand OF tramadol hydrochloride	HMDB
Clonmel brand OF tramadol hydrochloride	HMDB
Contramal	HMDB
Elerte brand OF tramadol hydrochloride	HMDB
Expanscience brand OF tramadol hydrochloride	HMDB
Hameln brand OF tramadol hydrochloride	HMDB
Jutadol	HMDB
Knoll brand OF tramadol hydrochloride	HMDB
Krewel brand OF tramadol hydrochloride	HMDB
MTWTramadol	HMDB
Medix brand OF tramadol hydrochloride	HMDB
TAD brand OF tramadol hydrochloride	HMDB
Theradol	HMDB
Tiral	HMDB
Tradol puren	HMDB
Tradonal	HMDB
Trama-dorsch	HMDB
TramaDorsch	HMDB
Tramadin	HMDB
Tramadoc	HMDB
Tramadol 1a	HMDB
Tramadol al	HMDB
Tramadol bayvit	HMDB
Tramadol mabo	HMDB
Tramadol PB	HMDB
Tramadol acis	HMDB
TramadolDolgit	HMDB
Tramadolor	HMDB
Tramagetic	HMDB
Tramagit	HMDB
Zambon brand OF tramadol hydrochloride	HMDB
Zamudol	HMDB
Zytram	HMDB
Betapharm brand OF tramadol hydrochloride	HMDB
Aliud brand OF tramadol hydrochloride	HMDB
Amadol	HMDB
CSL Brand OF tramadol hydrochloride	HMDB
Christiaens brand OF tramadol hydrochloride	HMDB
Erempharma brand OF tramadol hydrochloride	HMDB
Grunenthal brand OF tramadol hydrochloride	HMDB
Heumann brand OF tramadol hydrochloride	HMDB
Juta brand OF tramadol hydrochloride	HMDB
Kern brand OF tramadol hydrochloride	HMDB
Lakeside brand OF tramadol hydrochloride	HMDB
Lichtenstein brand OF tramadol hydrochloride	HMDB
Mundipharma brand OF tramadol hydrochloride	HMDB
Nobligan	HMDB
Ortho brand OF tramadol hydrochloride	HMDB
Ranitidin 1a pharma	HMDB
Ratiopharm brand OF tramadol hydrochloride	HMDB
Searle brand OF tramadol hydrochloride	HMDB
Stadapharm brand OF tramadol hydrochloride	HMDB
Takadol	HMDB
Topalgic	HMDB
Tradol	HMDB
Tralgiol	HMDB
Trama abz	HMDB
Tramadol hydrochloride	HMDB
Tramadol normon	HMDB
Tramadol-hameln	HMDB
Tramadol-ratiopharm	HMDB
Tramadolratiopharm	HMDB
Tramake	HMDB
Trasedal	HMDB
Viatris brand OF tramadol	HMDB
Acis brand OF tramadol hydrochloride	HMDB
Allphar brand OF tramadol hydrochloride	HMDB
Antigen brand OF tramadol hydrochloride	HMDB
Azupharma brand OF tramadol hydrochloride	HMDB
Basics brand OF tramadol hydrochloride	HMDB
Biocodex brand OF tramadol hydrochloride	HMDB
Biokanol	HMDB
Docpharm brand OF tramadol hydrochloride	HMDB
Janssen brand OF tramadol hydrochloride	HMDB
Kade brand OF tramadol hydrochloride	HMDB
MTW-Tramadol	HMDB
Merck dura brand OF tramadol hydrochloride	HMDB
Normon brand OF tramadol hydrochloride	HMDB
Prontofort	HMDB
Q Pharm brand OF tramadol hydrochloride	HMDB
Trama dorsch	HMDB
Tramabeta	HMDB
Tramadol basics	HMDB
Tramadol cinfa	HMDB
Tramadol dolgit	HMDB
Tramadol hameln	HMDB
Tramadol heumann	HMDB
Tramadol kern	HMDB
Tramadol lichtenstein	HMDB
Tramadol lindo	HMDB
Tramadol stada	HMDB
Tramadol viatris brand	HMDB
Tramadol-dolgit	HMDB
Tramadura	HMDB
Tramal	HMDB
Tramex	HMDB
Tramundin	HMDB
Xymel 50	HMDB
Zumalgic	HMDB

Chemical Formula

C₁₆H₂₅NO₂

Average Molecular Weight

263.3752

Monoisotopic Molecular Weight

263.188529049

IUPAC Name

(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol

Traditional Name

tramadol

CAS Registry Number

27203-92-5

SMILES

COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C

InChI Identifier

InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3/t14-,16+/m1/s1

InChI Key

TVYLLZQTGLZFBW-ZBFHGGJFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Cyclohexanol
Aralkylamine
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Ether
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol (CHEBI:75725 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014339)

Source

Exogenous

Exogenous (HMDB: HMDB0014339)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tramadol Metabolism Pathway (PathBank: SMP0000637)

Drug action pathway

Tramadol Action Action Pathway (PathBank: SMP0000671)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180 - 181 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.75 g/L	Not Available
LogP	2.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	161.4	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.75 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.45	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.27 m³·mol⁻¹	ChemAxon
Polarizability	30.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.051	31661259
DarkChem	[M-H]-	162.94	31661259
DeepCCS	[M+H]+	167.481	30932474
DeepCCS	[M-H]-	165.123	30932474
DeepCCS	[M-2H]-	198.889	30932474
DeepCCS	[M+Na]+	174.115	30932474
AllCCS	[M+H]+	163.3	32859911
AllCCS	[M+H-H2O]+	159.7	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	169.3	32859911
AllCCS	[M+Na-2H]-	169.7	32859911
AllCCS	[M+HCOO]-	170.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tramadol	COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C	2579.4	Standard polar	33892256
Tramadol	COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C	1988.6	Standard non polar	33892256
Tramadol	COC1=CC=CC(=C1)[C@@]1(O)CCCC[C@@H]1CN(C)C	1966.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tramadol,1TMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN(C)C)=C1	1946.0	Semi standard non polar	33892256
Tramadol,1TBDMS,isomer #1	COC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN(C)C)=C1	2191.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tramadol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9650000000-250d842ef06233328170	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tramadol GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-5193000000-dd2e84f70a47d0634c43	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tramadol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tramadol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9010000000-ffea37e400f0860f2e7f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-qTof , Positive-QTOF	splash10-03di-0090000000-1550dc2447717d7d8728	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-QTOF , positive-QTOF	splash10-03di-0090000000-7850be0ba78033f1f677	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-QTOF , positive-QTOF	splash10-03di-0090000000-62a3c5cb6717bff20e2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-QTOF , positive-QTOF	splash10-05fs-0930000000-b8297a71c45e9630f6c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-QTOF , positive-QTOF	splash10-05fr-0900000000-f650c49b70db20869d0f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-QTOF , positive-QTOF	splash10-0adl-0900000000-b17dfc32e2eb57efaf42	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0002-0090000000-c35bec467cfec28511fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-03di-1090000000-9ca08dcdc5a2027bcb03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9030000000-469467d2583e7202d89f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-89f055b497c88cdc5e79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-1922068301c6d3b4f457	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-1922068301c6d3b4f457	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-5a9396f20ce15b9c08ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-03di-1090000000-e040861e9fa18a8f44a5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9030000000-fa1522b6a491e6da41c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-8ab0ebc3ceff7c5e5ce5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-7645dc9b29d8b2867495	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-70cad0a31ff2d57bab81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tramadol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9000000000-bf1b2c15c6511355c9e1	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramadol 10V, Positive-QTOF	splash10-01ot-0090000000-7fe9a41fb060355ba0c0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramadol 20V, Positive-QTOF	splash10-0hft-1190000000-8c3c0de6df7ced23802a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramadol 40V, Positive-QTOF	splash10-0pbc-9120000000-4f0e74f6721de4ccf067	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramadol 10V, Negative-QTOF	splash10-03di-0090000000-24bef5bd2510914bee83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramadol 20V, Negative-QTOF	splash10-03di-1490000000-3314217686d7d48bff0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramadol 40V, Negative-QTOF	splash10-0a4l-9380000000-76c818434cc5aeed5aca	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tramadol Metabolism Pathway		Not Available
Tramadol Action Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00193	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00193	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00193

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31105

KEGG Compound ID

C07153

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tramadol

METLIN ID

Not Available

PubChem Compound

33741

PDB ID

Not Available

ChEBI ID

75725

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Dayer P, Desmeules J, Collart L: [Pharmacology of tramadol]. Drugs. 1997;53 Suppl 2:18-24. [PubMed:9190321 ]
Gobel H, Stadler T: [Treatment of post-herpes zoster pain with tramadol. Results of an open pilot study versus clomipramine with or without levomepromazine]. Drugs. 1997;53 Suppl 2:34-9. [PubMed:9190323 ]
Harati Y, Gooch C, Swenson M, Edelman S, Greene D, Raskin P, Donofrio P, Cornblath D, Sachdeo R, Siu CO, Kamin M: Double-blind randomized trial of tramadol for the treatment of the pain of diabetic neuropathy. Neurology. 1998 Jun;50(6):1842-6. [PubMed:9633738 ]
Harati Y, Gooch C, Swenson M, Edelman SV, Greene D, Raskin P, Donofrio P, Cornblath D, Olson WH, Kamin M: Maintenance of the long-term effectiveness of tramadol in treatment of the pain of diabetic neuropathy. J Diabetes Complications. 2000 Mar-Apr;14(2):65-70. [PubMed:10959067 ]
Boureau F, Legallicier P, Kabir-Ahmadi M: Tramadol in post-herpetic neuralgia: a randomized, double-blind, placebo-controlled trial. Pain. 2003 Jul;104(1-2):323-31. [PubMed:12855342 ]
(). FDA label . .

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Delta-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:: OPRD1
Uniprot ID:: P41143
Molecular weight:: 40412.3

References

Wentland MP, Lou R, Lu Q, Bu Y, VanAlstine MA, Cohen DJ, Bidlack JM: Syntheses and opioid receptor binding properties of carboxamido-substituted opioids. Bioorg Med Chem Lett. 2009 Jan 1;19(1):203-8. doi: 10.1016/j.bmcl.2008.10.134. Epub 2008 Nov 7. [PubMed:19027293 ]

Enzyme Details

5. Mu-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:: OPRM1
Uniprot ID:: P35372
Molecular weight:: 44778.9

References

Gillen C, Haurand M, Kobelt DJ, Wnendt S: Affinity, potency and efficacy of tramadol and its metabolites at the cloned human mu-opioid receptor. Naunyn Schmiedebergs Arch Pharmacol. 2000 Aug;362(2):116-21. [PubMed:10961373 ]
Potschka H, Friderichs E, Loscher W: Anticonvulsant and proconvulsant effects of tramadol, its enantiomers and its M1 metabolite in the rat kindling model of epilepsy. Br J Pharmacol. 2000 Sep;131(2):203-12. [PubMed:10991912 ]
Raffa RB, Friderichs E, Reimann W, Shank RP, Codd EE, Vaught JL: Opioid and nonopioid components independently contribute to the mechanism of action of tramadol, an 'atypical' opioid analgesic. J Pharmacol Exp Ther. 1992 Jan;260(1):275-85. [PubMed:1309873 ]
Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [PubMed:15509185 ]
Ide S, Minami M, Ishihara K, Uhl GR, Sora I, Ikeda K: Mu opioid receptor-dependent and independent components in effects of tramadol. Neuropharmacology. 2006 Sep;51(3):651-8. Epub 2006 Jun 21. [PubMed:16793069 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Minami K, Uezono Y, Ueta Y: Pharmacological aspects of the effects of tramadol on G-protein coupled receptors. J Pharmacol Sci. 2007 Mar;103(3):253-60. [PubMed:17380034 ]
Frink MC, Hennies HH, Englberger W, Haurand M, Wilffert B: Influence of tramadol on neurotransmitter systems of the rat brain. Arzneimittelforschung. 1996 Nov;46(11):1029-36. [PubMed:8955860 ]

Enzyme Details

6. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Ogata J, Minami K, Uezono Y, Okamoto T, Shiraishi M, Shigematsu A, Ueta Y: The inhibitory effects of tramadol on 5-hydroxytryptamine type 2C receptors expressed in Xenopus oocytes. Anesth Analg. 2004 May;98(5):1401-6, table of contents. [PubMed:15105221 ]
Horishita T, Minami K, Uezono Y, Shiraishi M, Ogata J, Okamoto T, Shigematsu A: The tramadol metabolite, O-desmethyl tramadol, inhibits 5-hydroxytryptamine type 2C receptors expressed in Xenopus Oocytes. Pharmacology. 2006;77(2):93-9. Epub 2006 May 5. [PubMed:16679816 ]

Enzyme Details

7. Glutamate [NMDA] receptor subunit 3A

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:: GRIN3A
Uniprot ID:: Q8TCU5
Molecular weight:: 125464.1

References

Hara K, Minami K, Sata T: The effects of tramadol and its metabolite on glycine, gamma-aminobutyric acidA, and N-methyl-D-aspartate receptors expressed in Xenopus oocytes. Anesth Analg. 2005 May;100(5):1400-5, table of contents. [PubMed:15845694 ]

Enzyme Details

8. Kappa-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:: OPRK1
Uniprot ID:: P41145
Molecular weight:: 42644.7

References

Sun HL, Zheng JW, Wang K, Liu RK, Liang JH: Tramadol reduces the 5-HTP-induced head-twitch response in mice via the activation of mu and kappa opioid receptors. Life Sci. 2003 Jan 31;72(11):1221-30. [PubMed:12570923 ]

Enzyme Details

9. Muscarinic acetylcholine receptor M3

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular weight:: 66127.4

References

Shiraishi M, Minami K, Uezono Y, Yanagihara N, Shigematsu A: Inhibition by tramadol of muscarinic receptor-induced responses in cultured adrenal medullary cells and in Xenopus laevis oocytes expressing cloned M1 receptors. J Pharmacol Exp Ther. 2001 Oct;299(1):255-60. [PubMed:11561087 ]
Shiga Y, Minami K, Shiraishi M, Uezono Y, Murasaki O, Kaibara M, Shigematsu A: The inhibitory effects of tramadol on muscarinic receptor-induced responses in Xenopus oocytes expressing cloned M(3) receptors. Anesth Analg. 2002 Nov;95(5):1269-73, table of contents. [PubMed:12401609 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Sagata K, Minami K, Yanagihara N, Shiraishi M, Toyohira Y, Ueno S, Shigematsu A: Tramadol inhibits norepinephrine transporter function at desipramine-binding sites in cultured bovine adrenal medullary cells. Anesth Analg. 2002 Apr;94(4):901-6, table of contents. [PubMed:11916794 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Berrocoso E, Mico JA: Cooperative opioid and serotonergic mechanisms generate superior antidepressant-like effects in a mice model of depression. Int J Neuropsychopharmacol. 2009 Sep;12(8):1033-44. doi: 10.1017/S1461145709000236. Epub 2009 Apr 3. [PubMed:19341511 ]
Frink MC, Hennies HH, Englberger W, Haurand M, Wilffert B: Influence of tramadol on neurotransmitter systems of the rat brain. Arzneimittelforschung. 1996 Nov;46(11):1029-36. [PubMed:8955860 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Barann M, Urban B, Stamer U, Dorner Z, Bonisch H, Bruss M: Effects of tramadol and O-demethyl-tramadol on human 5-HT reuptake carriers and human 5-HT3A receptors: a possible mechanism for tramadol-induced early emesis. Eur J Pharmacol. 2006 Feb 15;531(1-3):54-8. Epub 2006 Jan 19. [PubMed:16427041 ]
Driessen B, Reimann W: Interaction of the central analgesic, tramadol, with the uptake and release of 5-hydroxytryptamine in the rat brain in vitro. Br J Pharmacol. 1992 Jan;105(1):147-51. [PubMed:1596676 ]
Frink MC, Hennies HH, Englberger W, Haurand M, Wilffert B: Influence of tramadol on neurotransmitter systems of the rat brain. Arzneimittelforschung. 1996 Nov;46(11):1029-36. [PubMed:8955860 ]

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

Show all enzymes and transporters

Showing metabocard for Tramadol (HMDB0014339)

MOL for HMDB0014339 (Tramadol)

3D MOL for HMDB0014339 (Tramadol)

3D SDF for HMDB0014339 (Tramadol)

3D-SDF for HMDB0014339 (Tramadol)

PDB for HMDB0014339 (Tramadol)

3D PDB for HMDB0014339 (Tramadol)

SMILES for HMDB0014339 (Tramadol)

INCHI for HMDB0014339 (Tramadol)

Structure for HMDB0014339 (Tramadol)

3D Structure for HMDB0014339 (Tramadol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

Transporters

References

References