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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:08 UTC
HMDB IDHMDB0000398
Secondary Accession Numbers
  • HMDB00398
Metabolite Identification
Common Name3-Oxoadipic acid
Description3-Oxoadipic acid, also known as 3-keto-adipate or b-oxoadipate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 3-Oxoadipic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Oxoadipic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752128
Synonyms
ValueSource
3-Keto-adipateChEBI
beta-Ketoadipic acidChEBI
beta-Oxoadipic acidChEBI
3-Keto-adipic acidGenerator
b-KetoadipateGenerator
b-Ketoadipic acidGenerator
beta-KetoadipateGenerator
Β-ketoadipateGenerator
Β-ketoadipic acidGenerator
b-OxoadipateGenerator
b-Oxoadipic acidGenerator
beta-OxoadipateGenerator
Β-oxoadipateGenerator
Β-oxoadipic acidGenerator
3-OxoadipateGenerator
3-KetoadipateHMDB
3-Ketoadipic acidHMDB
3-OxohexanedioateHMDB
3-Oxohexanedioic acidHMDB
3-Oxoadipic acid, disodium saltHMDB
3-KetoadipicHMDB
3-oxo-AdipateHMDB
3-Oxoadipic acidKEGG
Chemical FormulaC6H8O5
Average Molecular Weight160.1247
Monoisotopic Molecular Weight160.037173366
IUPAC Name3-oxohexanedioic acid
Traditional Name3-oxoadipic acid
CAS Registry Number689-31-6
SMILES
OC(=O)CCC(=O)CC(O)=O
InChI Identifier
InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChI KeyRTGHRDFWYQHVFW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Gamma-keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Beta-hydroxy ketone
  • Ketone
  • 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
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point124 - 126 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility37.1 g/LALOGPS
logP-0.64ALOGPS
logP-0.18ChemAxon
logS-0.64ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity33.43 m³·mol⁻¹ChemAxon
Polarizability13.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00fr-9300000000-72c6f8e091fde59fcc6dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00di-9300000000-e16f3c7e8cbd3eecdd53Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00fr-9300000000-72c6f8e091fde59fcc6dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9300000000-e16f3c7e8cbd3eecdd53Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9200000000-edd79fa9b71a6b08c581Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-9260000000-e0e8f0b98c96b6e1fdd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-96c5f05fc6b878ab1851Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-d66b7b214be6f5603f36Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0900000000-90f1b6b3fb1700353565Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-bc4f5be039aaafe91dd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ke-9800000000-8e8faa9566cb5d032186Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aov-9000000000-a3065ccf178062c46321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aou-1900000000-fbef6dc5f8198d5bd637Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066s-9800000000-4882dffcd1d4aaccb3bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mn-9100000000-7fb63533f517e56117f8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022015
KNApSAcK IDNot Available
Chemspider ID91
KEGG Compound IDC00846
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5387
PubChem Compound93
PDB IDNot Available
ChEBI ID37440
Food Biomarker OntologyNot Available
VMH ID3OXOADP
MarkerDB ID
References
Synthesis ReferenceDarrah, Josephine A.; Cain, Ronald B. Convenient biological method for preparing beta-ketoadipic acid. Laboratory Practice (1967), 16(8), 989-90.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Svendsen JS, Sydnes LK, Whist JE: Identification of 3-oxodicarboxylic acids in human urine. J Chromatogr. 1988 Nov 18;432:13-9. [PubMed:3220884 ]