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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:37 UTC
HMDB IDHMDB00398
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Oxoadipic acid
Description3-Oxoadipic acid is a regularly occurring Adipic dicarboxylic acid human metabolite found occasionally in biofluids of healthy individuals. (PMIDs 8340451, 1769109, 2338430) Increased amounts of 3-Oxoadipic acid are excreted after ingestion of Sebacic acid, supporting the hypothesis that dicarboxylic acids are degraded by ordinary beta-oxidation. (PMID 3220884 ).
Structure
Thumb
Synonyms
ValueSource
3-keto-AdipateChEBI
beta-Ketoadipic acidChEBI
beta-Oxoadipic acidChEBI
3-keto-Adipic acidGenerator
3-OxoadipateGenerator
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-KetoadipateHMDB
3-Ketoadipic acidHMDB
3-OxohexanedioateHMDB
3-Oxohexanedioic acidHMDB
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 KeyInChIKey=RTGHRDFWYQHVFW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity33.43 m3·mol-1ChemAxon
Polarizability13.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00fr-9300000000-72c6f8e091fde59fcc6dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00di-9300000000-e16f3c7e8cbd3eecdd53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-96c5f05fc6b878ab1851View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-d66b7b214be6f5603f36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0900000000-90f1b6b3fb1700353565View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022015
KNApSAcK IDNot Available
Chemspider ID91
KEGG Compound IDC00846
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00398
Metagene LinkHMDB00398
METLIN ID5387
PubChem Compound93
PDB IDNot Available
ChEBI ID37440
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. [3220884 ]