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Showing metabocard for Acetoacetic acid (HMDB0000060)

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enzymes (10) Show 10 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:29 UTC
HMDB IDHMDB0000060
Secondary Accession Numbers
  • HMDB00060
Metabolite Identification
Common NameAcetoacetic acid
DescriptionAcetoacetic acid (AcAc) is a weak organic acid that can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis). It is then partially converted into acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first two weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391 ). The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected.
Structure
Data?1676999669
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000060 (Acetoacetic acid)

            
  Mrv1652309032023512D          

  7  6  0  0  0  0            999 V2000
    2.0480    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    1.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101    0.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for HMDB0000060 (Acetoacetic acid)

HMDB0000060
     RDKit          3D
Acetoacetic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.6992    0.3663   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827    0.0218    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8466    0.4764    1.8564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5028   -0.8131    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161   -0.2493   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -1.0467   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    1.1154   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    1.4525   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.2860   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    0.1410   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -0.8730    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -1.8617    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    1.5565    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  4 12  1  0
  7 13  1  0
M  END
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3D SDF for HMDB0000060 (Acetoacetic acid)

            
  Mrv1652309032023512D          

  7  6  0  0  0  0            999 V2000
    2.0480    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    1.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101    0.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955    1.3334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000060

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)

> <INCHI_KEY>
WDJHALXBUFZDSR-UHFFFAOYSA-N

> <FORMULA>
C4H6O3

> <MOLECULAR_WEIGHT>
102.0886

> <EXACT_MASS>
102.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.179267520270244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxobutanoic acid

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-0.0014917456666668494

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.223356862546826

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.024917062647246

> <JCHEM_PKA_STRONGEST_BASIC>
-7.473176600242656

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
22.5389

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetoacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000060 (Acetoacetic acid)

HMDB0000060
     RDKit          3D
Acetoacetic acid
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.6992    0.3663   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827    0.0218    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8466    0.4764    1.8564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5028   -0.8131    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161   -0.2493   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617   -1.0467   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    1.1154   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    1.4525   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.2860   -0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    0.1410   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -0.8730    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -1.8617    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    1.5565    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  4 12  1  0
  7 13  1  0
M  END
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PDB for HMDB0000060 (Acetoacetic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       3.823   0.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.489   0.949   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.489   2.489   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.155   0.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.178   0.949   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.512   0.179   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.178   2.489   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0000060 (Acetoacetic acid)

COMPND    HMDB0000060
HETATM    1  C1  UNL     1      -1.699   0.366  -0.276  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.683   0.022   0.731  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.847   0.476   1.856  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.503  -0.813   0.487  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.416  -0.249  -0.532  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.962  -1.047  -1.328  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.605   1.115  -0.539  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.955   1.452  -0.306  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.575  -0.286  -0.108  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.323   0.141  -1.320  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.122  -0.873   1.430  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.221  -1.862   0.283  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.253   1.556   0.126  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    4
CONECT    4    5   11   12
CONECT    5    6    6    7
CONECT    7   13
END
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SMILES for HMDB0000060 (Acetoacetic acid)

CC(=O)CC(O)=O
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INCHI for HMDB0000060 (Acetoacetic acid)

InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Ketobutanoic acidChEBI
3-Ketobutyric acidChEBI
3-Oxobutanoic acidChEBI
3-Oxobutyric acidChEBI
beta-Ketobutyric acidChEBI
3-KetobutanoateGenerator
3-KetobutyrateGenerator
3-OxobutanoateGenerator
3-OxobutyrateGenerator
b-KetobutyrateGenerator
b-Ketobutyric acidGenerator
beta-KetobutyrateGenerator
Β-ketobutyrateGenerator
Β-ketobutyric acidGenerator
AcetoacetateGenerator
Acetoacetic acid, calcium saltMeSH
Acetoacetic acid, lithium saltMeSH
Acetoacetic acid, sodium saltMeSH
OxobutyrateMeSH
Sodium acetoacetateMeSH
3-oxo-ButanoateHMDB
3-oxo-Butanoic acidHMDB
DiacetateHMDB
Diacetic acidHMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name3-oxobutanoic acid
Traditional Nameacetoacetic acid
CAS Registry Number541-50-4
SMILES
CC(=O)CC(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
InChI KeyWDJHALXBUFZDSR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Beta-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point36.5 °CNot Available
Boiling Point237.00 to 239.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.467 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility240 g/LALOGPS
logP-0.47ALOGPS
logP-0.0015ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.54 m³·mol⁻¹ChemAxon
Polarizability9.18 ųChemAxon
Number of Rings0ChemAxon
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]+120.95131661259
DarkChem[M-H]-113.61931661259
AllCCS[M+H]+124.91832859911
AllCCS[M-H]-122.76732859911
DeepCCS[M+H]+128.03130932474
DeepCCS[M-H]-125.26930932474
DeepCCS[M-2H]-161.59230932474
DeepCCS[M+Na]+136.45330932474
AllCCS[M+H]+124.932859911
AllCCS[M+H-H2O]+120.632859911
AllCCS[M+NH4]+129.032859911
AllCCS[M+Na]+130.232859911
AllCCS[M-H]-122.832859911
AllCCS[M+Na-2H]-126.632859911
AllCCS[M+HCOO]-130.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetoacetic acidCC(=O)CC(O)=O1962.1Standard polar33892256
Acetoacetic acidCC(=O)CC(O)=O859.8Standard non polar33892256
Acetoacetic acidCC(=O)CC(O)=O972.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetoacetic acid,1TMS,isomer #1CC(=O)CC(=O)O[Si](C)(C)C1039.7Semi standard non polar33892256
Acetoacetic acid,1TMS,isomer #2CC(=CC(=O)O)O[Si](C)(C)C1168.5Semi standard non polar33892256
Acetoacetic acid,1TMS,isomer #3C=C(CC(=O)O)O[Si](C)(C)C1143.1Semi standard non polar33892256
Acetoacetic acid,2TMS,isomer #1CC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1234.5Semi standard non polar33892256
Acetoacetic acid,2TMS,isomer #1CC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1195.5Standard non polar33892256
Acetoacetic acid,2TMS,isomer #1CC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1227.9Standard polar33892256
Acetoacetic acid,2TMS,isomer #2C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1187.7Semi standard non polar33892256
Acetoacetic acid,2TMS,isomer #2C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1207.9Standard non polar33892256
Acetoacetic acid,2TMS,isomer #2C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1275.0Standard polar33892256
Acetoacetic acid,1TBDMS,isomer #1CC(=O)CC(=O)O[Si](C)(C)C(C)(C)C1256.0Semi standard non polar33892256
Acetoacetic acid,1TBDMS,isomer #2CC(=CC(=O)O)O[Si](C)(C)C(C)(C)C1396.0Semi standard non polar33892256
Acetoacetic acid,1TBDMS,isomer #3C=C(CC(=O)O)O[Si](C)(C)C(C)(C)C1350.4Semi standard non polar33892256
Acetoacetic acid,2TBDMS,isomer #1CC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1638.4Semi standard non polar33892256
Acetoacetic acid,2TBDMS,isomer #1CC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1637.3Standard non polar33892256
Acetoacetic acid,2TBDMS,isomer #1CC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1558.1Standard polar33892256
Acetoacetic acid,2TBDMS,isomer #2C=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1617.7Semi standard non polar33892256
Acetoacetic acid,2TBDMS,isomer #2C=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1620.4Standard non polar33892256
Acetoacetic acid,2TBDMS,isomer #2C=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1584.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kk-3940000000-008eb78d2ba3cfa053b42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (1 MEOX; 1 TMS)splash10-000i-9500000000-c3940e591f8aef9d6aac2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (1 MEOX; 1 TMS)splash10-000i-9800000000-67a95675672c3f5447a72014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (2 TMS)splash10-001i-4950000000-1778836b3908a79b814f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (2 TMS)splash10-001i-4950000000-4039bb48c98ec17b5c0c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-EI-TOF (Non-derivatized)splash10-00kk-3940000000-008eb78d2ba3cfa053b42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (Non-derivatized)splash10-000i-9500000000-c3940e591f8aef9d6aac2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (Non-derivatized)splash10-000i-9800000000-67a95675672c3f5447a72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (Non-derivatized)splash10-001i-4950000000-1778836b3908a79b814f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoacetic acid GC-MS (Non-derivatized)splash10-001i-4950000000-4039bb48c98ec17b5c0c2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9f6c0d100736f4d183c92016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0100-9600000000-470bf0676151478bca3e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoacetic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8cc2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba282012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid , positive-QTOFsplash10-000i-9100000000-869e2338bbadb32272d42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid n/a 7V, negative-QTOFsplash10-0a4i-9000000000-3f979a5a82ec557199d22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid 20V, Negative-QTOFsplash10-000f-9000000000-2b35e5493fb76f714c222021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid 10V, Negative-QTOFsplash10-05fr-9000000000-d2734268ae2c1230e50f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetoacetic acid 40V, Negative-QTOFsplash10-00di-9000000000-0d73b25163774c0d1eb12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 10V, Positive-QTOFsplash10-0f79-9400000000-081c4a1a05f5581a5ffb2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 20V, Positive-QTOFsplash10-000l-9100000000-960a06fd90db43d3e0f62016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 40V, Positive-QTOFsplash10-0006-9000000000-bd091454ccc8f532b42e2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 10V, Negative-QTOFsplash10-0zfr-9700000000-b01f47bb6cd4f10439832016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 20V, Negative-QTOFsplash10-0a4i-9100000000-d2649829e8a79045e73b2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-1486ce68d51ba83ed4992016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 10V, Negative-QTOFsplash10-0pb9-9400000000-2f187d15e3b22b7629d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 20V, Negative-QTOFsplash10-0a4i-9100000000-1e5e193606848f9d64b42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 40V, Negative-QTOFsplash10-0a4l-9000000000-73a6b61cfeb4b8ae96122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 10V, Positive-QTOFsplash10-0006-9000000000-de86214ccec455e1860b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 20V, Positive-QTOFsplash10-0006-9000000000-42af30a03d7e2d4c22fc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoacetic acid 40V, Positive-QTOFsplash10-0006-9000000000-6aa1f4078505fa3b09712021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H 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)2012-12-04Wishart 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
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
  • Leukocyte
  • Liver
  • Neuron
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified21.0 (0.0-86.0) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified37.75(25.96) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified30-1400 uMNot SpecifiedNot SpecifiedNormal details
BloodDetected and Quantified0.0-86.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<150 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified20-90 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified40.6 +/- 36.5 uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified1700 (1500-1900) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified26.2 +/- 12.3 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified12.0 +/- 14.0 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified6.0 +/- 6.0 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified26.2 +/- 12.3 uMNot SpecifiedNot SpecifiedNormal
    • Geigy Scientific ...
 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 QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified10.70 +/- 4.33 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified0.15 (0.01-0.58) umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.20 (0.020-0.82) umol/mmol creatinineAdult (>18 years old)Female
Normal		 details
UrineDetected and Quantified11.1 (2.2-24.9) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified18.64 +/- 20.321 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified33.0(0.00-67.0) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified5-28 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified27.3 +/- 14.4 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected and Quantified19.56 +/- 10.63 uMAdult (>18 years old)Female
Pregnancy with fetuses with trisomy 18		 details
BloodDetected and Quantified16.15 +/- 9.18 uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified14.5 (5.1) uMAdult (>18 years old)FemaleEarly preeclampsia details
BloodDetected and Quantified18.8 (9.7) uMAdult (>18 years old)FemalePregnancy details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia		 details
BloodDetected and Quantified3030.0 +/- 20.0 uMAdult (>18 years old)Both
Diabetes		 details
BloodDetected and Quantified14.33 (10.92) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified12.64 (8.21) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified18.9 (9.8) uMAdult (>18 years old)FemaleLate-onset preeclampsia details
BloodDetected and Quantified16.5 (9.6) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified26.27(34.57) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified100 uMNewborn (0-30 days old)Male2-Ketoglutarate dehydrogenase complex deficiency details
BloodDetected and Quantified50-1280 uMChildren (1-13 years old)Male2-Ketoglutarate dehydrogenase complex deficiency details
BloodDetected and Quantified910 uMChildren (1-13 years old)Male
Succinyl CoA: 3-ketoacid CoA transferase deficiency		 details
BloodDetected and Quantified1540 uMChildren (1-13 years old)Male
Succinyl CoA: 3-ketoacid CoA transferase deficiency		 details
BloodDetected and Quantified360 uMInfant (0-1 year old)MalePyruvate dehydrogenase phosphatase deficiency details
BloodDetected and Quantified23.5 (24.3) uMAdult (>18 years old)FemaleDown syndrome pregnancy details
BloodDetected and Quantified13.9 (7.3) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified<30 uMChildren (1-13 years old)Male
3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency		 details
Cellular CytoplasmDetected and Quantified1000 (800-1200) uMAdult (>18 years old)BothAnoxia details
Cerebrospinal Fluid (CSF)Detected and Quantified248 +/- 179 uMChildren (1-13 years old)Not SpecifiedGlucose transporter type 1 deficiency syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified322.0 (240.0-404.0) uMAdult (>18 years old)Both
Meningitis		 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 QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable Bowel Syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified1.6 (0.2-5.8) umol/mmol creatinineChildren (1-13 years old)BothKetosis
    • Physician's Guide...
 details
UrineDetected and Quantified0.1 (0-1.5) umol/mmol creatinineInfant (0-1 year old)BothKetosis
    • Physician's Guide...
 details
UrineDetected and Quantified0.08 (0-1.5) umol/mmol creatinineNewborn (0-30 days old)BothKetosis
    • Physician's Guide...
 details
UrineDetected and Quantified22.37 +/- 14.614 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified237.0 umol/mmol creatinineAdult (>18 years old)BothDiabetes details
UrineDetected and Quantified1.00 (0.00-2.00) umol/mmol creatinineAdult (>18 years old)Both
Ketosis
    • MetaGene: Metabol...
 details
UrineDetected and Quantified10025.00 (50.00-20000.00) umol/mmol creatinineChildren (1-13 years old)BothKetosis
    • MetaGene: Metabol...
 details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Tasker RC, Lutman D, Peters MJ: Hyperventilation in severe diabetic ketoacidosis. Pediatr Crit Care Med. 2005 Jul;6(4):405-11. [PubMed:15982426 ]
  2. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
Schizophrenia
  1. Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
  2. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
  3. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
  4. Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
  5. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Late-onset preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
2-Ketoglutarate dehydrogenase complex deficiency
  1. Guffon N, Lopez-Mediavilla C, Dumoulin R, Mousson B, Godinot C, Carrier H, Collombet JM, Divry P, Mathieu M, Guibaud P: 2-Ketoglutarate dehydrogenase deficiency, a rare cause of primary hyperlactataemia: report of a new case. J Inherit Metab Dis. 1993;16(5):821-30. [PubMed:8295396 ]
3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency
  1. Morris AA, Lascelles CV, Olpin SE, Lake BD, Leonard JV, Quant PA: Hepatic mitochondrial 3-hydroxy-3-methylglutaryl-coenzyme a synthase deficiency. Pediatr Res. 1998 Sep;44(3):392-6. doi: 10.1203/00006450-199809000-00021. [PubMed:9727719 ]
Ketoacidosis
  1. Snyderman SE, Sansaricq C, Middleton B: Succinyl-CoA:3-ketoacid CoA-transferase deficiency. Pediatrics. 1998 Apr;101(4 Pt 1):709-11. [PubMed:9521962 ]
Pyruvate dehydrogenase phosphatase deficiency
  1. Robinson BH, Sherwood WG: Pyruvate dehydrogenase phosphatase deficiency: a cause of congenital chronic lactic acidosis in infancy. Pediatr Res. 1975 Dec;9(12):935-9. doi: 10.1203/00006450-197512000-00015. [PubMed:172850 ]
Anoxia
  1. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
Glucose transporter type 1 deficiency syndrome
  1. Klepper J, Diefenbach S, Kohlschutter A, Voit T: Effects of the ketogenic diet in the glucose transporter 1 deficiency syndrome. Prostaglandins Leukot Essent Fatty Acids. 2004 Mar;70(3):321-7. [PubMed:14769490 ]
Meningitis
  1. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [PubMed:15627241 ]
Irritable bowel syndrome
  1. Hong YS, Hong KS, Park MH, Ahn YT, Lee JH, Huh CS, Lee J, Kim IK, Hwang GS, Kim JS: Metabonomic understanding of probiotic effects in humans with irritable bowel syndrome. J Clin Gastroenterol. 2011 May-Jun;45(5):415-25. doi: 10.1097/MCG.0b013e318207f76c. [PubMed:21494186 ]
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 ]
Ulcerative colitis
  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 ]
Colorectal cancer
  1. 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 ]
  2. 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 ]
Ketosis
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
  2. Blau N, Duran M, Blaskovics ME, Gibson KM (2003). Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003. Springer.
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 125853 (Diabetes mellitus type 2)
  • 181500 (Schizophrenia)
  • 203740 (2-Ketoglutarate dehydrogenase complex deficiency)
  • 605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
  • 245050 (Ketoacidosis)
  • 608782 (Pyruvate dehydrogenase phosphatase deficiency)
  • 606777 (Glucose transporter type 1 deficiency syndrome)
  • 266600 (Crohn's disease)
  • 114500 (Colorectal cancer)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDDB01762
Phenol Explorer Compound IDNot Available
FooDB IDFDB112157
KNApSAcK IDC00007458
Chemspider ID94
KEGG Compound IDC00164
BioCyc ID3-KETOBUTYRATE
BiGG IDNot Available
Wikipedia LinkAcetoacetic_acid
METLIN IDNot Available
PubChem Compound96
PDB IDNot Available
ChEBI ID15344
Food Biomarker OntologyNot Available
VMH IDACAC
MarkerDB IDMDB00000030
Good Scents IDrw1468691
References
Synthesis ReferenceLopez-Soriano, F. J.; Argiles, J. M. A simple method for the preparation of acetoacetate. Analytical Letters (1985), 18(B5), 589-92.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  2. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  3. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [PubMed:15627241 ]
  4. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
  5. Heller MJ, Adams PW, Orosz CG: Evaluation of an automated method of percent reactive antibody determination. Hum Immunol. 1992 Nov;35(3):179-87. [PubMed:1293081 ]
  6. Tasker RC, Lutman D, Peters MJ: Hyperventilation in severe diabetic ketoacidosis. Pediatr Crit Care Med. 2005 Jul;6(4):405-11. [PubMed:15982426 ]
  7. Oligny LL, Lough J: Hepatic sinusoidal ectasia. Hum Pathol. 1992 Aug;23(8):953-6. [PubMed:1644440 ]
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Enzymes

Enzyme Details
1. Hydroxymethylglutaryl-CoA lyase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Key enzyme in ketogenesis (ketone body formation). Terminal step in leucine catabolism.
Gene Name:
HMGCL
Uniprot ID:
P35914
Molecular weight:
34359.84
Reactions
3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoA + Acetoacetic aciddetails
Enzyme Details
2. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Enzyme Details
3. D-beta-hydroxybutyrate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
BDH1
Uniprot ID:
Q02338
Molecular weight:
38156.77
Reactions
3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADHdetails
3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
4. Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial
General function:
Involved in CoA-transferase activity
Specific function:
Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate.
Gene Name:
OXCT1
Uniprot ID:
P55809
Molecular weight:
56157.175
Reactions
Succinyl-CoA + Acetoacetic acid → Succinic acid + Acetoacetyl-CoAdetails
Enzyme Details
5. Fumarylacetoacetase
General function:
Involved in fumarylacetoacetase activity
Specific function:
Not Available
Gene Name:
FAH
Uniprot ID:
P16930
Molecular weight:
46373.97
Reactions
4-Fumarylacetoacetic acid + Water → Acetoacetic acid + Fumaric aciddetails
Acetoacetic acid + Fumaric acid → 4-Fumarylacetoacetic acid + Waterdetails
Enzyme Details
6. Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrial
General function:
Involved in CoA-transferase activity
Specific function:
Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate (By similarity).
Gene Name:
OXCT2
Uniprot ID:
Q9BYC2
Molecular weight:
56139.41
Reactions
Succinyl-CoA + Acetoacetic acid → Succinic acid + Acetoacetyl-CoAdetails
Enzyme Details
7. Hydroxyacid-oxoacid transhydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
Gene Name:
ADHFE1
Uniprot ID:
Q8IWW8
Molecular weight:
50307.42
Reactions
(S)-3-Hydroxybutyric acid + Oxoglutaric acid → Acetoacetic acid + D-2-Hydroxyglutaric aciddetails
Enzyme Details
8. Acetoacetyl-CoA synthetase
General function:
Involved in acetoacetate-CoA ligase activity
Specific function:
Activates acetoacetate to acetoacetyl-CoA. May be involved in utilizing ketone body for the fatty acid-synthesis during adipose tissue development (By similarity).
Gene Name:
AACS
Uniprot ID:
Q86V21
Molecular weight:
75143.645
Reactions
Adenosine triphosphate + Acetoacetic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Acetoacetyl-CoAdetails
Enzyme Details
9. 3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmic
General function:
Involved in catalytic activity
Specific function:
Non-mitochondrial 3-hydroxymethyl-3-methylglutaryl-CoA lyase that catalyzes a cation-dependent cleavage of (S)-3-hydroxy-3-methylglutaryl-CoA into acetyl-CoA and acetoacetate, a key step in ketogenesis, the products of which support energy production in nonhepatic animal tissues.
Gene Name:
HMGCLL1
Uniprot ID:
Q8TB92
Molecular weight:
36327.465
Reactions
3-Hydroxy-3-methylglutaryl-CoA → Acetyl-CoA + Acetoacetic aciddetails
Enzyme Details
10. 3-hydroxybutyrate dehydrogenase type 2
General function:
Involved in oxidoreductase activity
Specific function:
Dehydrogenase that mediates the formation of 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderophore that shares structural similarities with bacterial enterobactin and associates with LCN2, thereby playing a key role in iron homeostasis and transport. Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
Gene Name:
BDH2
Uniprot ID:
Q9BUT1
Molecular weight:
26723.57
Reactions
3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADHdetails
3-Hydroxybutyric acid + NAD → Acetoacetic acid + NADH + Hydrogen Iondetails