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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:47 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 exists in all living organisms, ranging from bacteria to humans. 3-Oxoadipic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-oxoadipic acid a potential biomarker for the consumption of these foods. 3-Oxoadipic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 3-Oxoadipic acid.
Structure
Data?1676999687
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-KetoadipicHMDB
3-Oxoadipic acid, disodium saltHMDB
3-KetoadipateHMDB
3-Ketoadipic acidHMDB
3-OxohexanedioateHMDB
3-Oxohexanedioic acidHMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point124 - 126 °CNot Available
Boiling Point412.25 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.688 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.93531661259
DarkChem[M-H]-131.44731661259
AllCCS[M+H]+135.24832859911
AllCCS[M-H]-130.57732859911
DeepCCS[M+H]+129.32330932474
DeepCCS[M-H]-125.49430932474
DeepCCS[M-2H]-162.62230932474
DeepCCS[M+Na]+137.99630932474
AllCCS[M+H]+135.232859911
AllCCS[M+H-H2O]+131.332859911
AllCCS[M+NH4]+138.932859911
AllCCS[M+Na]+140.032859911
AllCCS[M-H]-130.632859911
AllCCS[M+Na-2H]-132.332859911
AllCCS[M+HCOO]-134.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Oxoadipic acidOC(=O)CCC(=O)CC(O)=O2533.9Standard polar33892256
3-Oxoadipic acidOC(=O)CCC(=O)CC(O)=O1175.7Standard non polar33892256
3-Oxoadipic acidOC(=O)CCC(=O)CC(O)=O1504.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Oxoadipic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC(=O)CC(=O)O1480.9Semi standard non polar33892256
3-Oxoadipic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CC(=O)CCC(=O)O1464.4Semi standard non polar33892256
3-Oxoadipic acid,1TMS,isomer #3C[Si](C)(C)OC(=CC(=O)O)CCC(=O)O1678.7Semi standard non polar33892256
3-Oxoadipic acid,1TMS,isomer #4C[Si](C)(C)OC(=CCC(=O)O)CC(=O)O1565.0Semi standard non polar33892256
3-Oxoadipic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCC(=O)CC(=O)O[Si](C)(C)C1600.3Semi standard non polar33892256
3-Oxoadipic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCC(=CC(=O)O)O[Si](C)(C)C1704.6Semi standard non polar33892256
3-Oxoadipic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)CC=C(CC(=O)O)O[Si](C)(C)C1643.4Semi standard non polar33892256
3-Oxoadipic acid,2TMS,isomer #4C[Si](C)(C)OC(=O)CC(=CCC(=O)O)O[Si](C)(C)C1635.8Semi standard non polar33892256
3-Oxoadipic acid,2TMS,isomer #5C[Si](C)(C)OC(=O)C=C(CCC(=O)O)O[Si](C)(C)C1697.1Semi standard non polar33892256
3-Oxoadipic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1712.9Semi standard non polar33892256
3-Oxoadipic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1704.5Standard non polar33892256
3-Oxoadipic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C1742.4Standard polar33892256
3-Oxoadipic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)CC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1689.1Semi standard non polar33892256
3-Oxoadipic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)CC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1692.1Standard non polar33892256
3-Oxoadipic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)CC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1748.7Standard polar33892256
3-Oxoadipic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC(=O)CC(=O)O1753.7Semi standard non polar33892256
3-Oxoadipic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC(=O)CCC(=O)O1737.0Semi standard non polar33892256
3-Oxoadipic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC(=O)O)CCC(=O)O1911.0Semi standard non polar33892256
3-Oxoadipic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CCC(=O)O)CC(=O)O1833.3Semi standard non polar33892256
3-Oxoadipic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC(=O)CC(=O)O[Si](C)(C)C(C)(C)C2044.3Semi standard non polar33892256
3-Oxoadipic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCC(=CC(=O)O)O[Si](C)(C)C(C)(C)C2188.0Semi standard non polar33892256
3-Oxoadipic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CC=C(CC(=O)O)O[Si](C)(C)C(C)(C)C2108.8Semi standard non polar33892256
3-Oxoadipic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C2093.9Semi standard non polar33892256
3-Oxoadipic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C=C(CCC(=O)O)O[Si](C)(C)C(C)(C)C2125.4Semi standard non polar33892256
3-Oxoadipic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2339.5Semi standard non polar33892256
3-Oxoadipic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2294.2Standard non polar33892256
3-Oxoadipic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2164.7Standard polar33892256
3-Oxoadipic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2336.9Semi standard non polar33892256
3-Oxoadipic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2298.6Standard non polar33892256
3-Oxoadipic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2159.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Oxoadipic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00fr-9300000000-72c6f8e091fde59fcc6d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Oxoadipic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00di-9300000000-e16f3c7e8cbd3eecdd532014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Oxoadipic acid GC-EI-TOF (Non-derivatized)splash10-00fr-9300000000-72c6f8e091fde59fcc6d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Oxoadipic acid GC-EI-TOF (Non-derivatized)splash10-00di-9300000000-e16f3c7e8cbd3eecdd532017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9200000000-edd79fa9b71a6b08c5812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0079-9260000000-e0e8f0b98c96b6e1fdd42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxoadipic acid GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Oxoadipic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-0900000000-96c5f05fc6b878ab18512012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Oxoadipic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-03di-0900000000-d66b7b214be6f5603f362012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Oxoadipic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-03di-0900000000-90f1b6b3fb17003535652012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 10V, Positive-QTOFsplash10-0006-1900000000-bc4f5be039aaafe91dd22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 20V, Positive-QTOFsplash10-00ke-9800000000-8e8faa9566cb5d0321862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 40V, Positive-QTOFsplash10-0aov-9000000000-a3065ccf178062c463212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 10V, Negative-QTOFsplash10-0aou-1900000000-fbef6dc5f8198d5bd6372017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 20V, Negative-QTOFsplash10-066s-9800000000-4882dffcd1d4aaccb3bd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 40V, Negative-QTOFsplash10-05mn-9100000000-7fb63533f517e56117f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 10V, Negative-QTOFsplash10-0002-9400000000-832431535450c51b56112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 20V, Negative-QTOFsplash10-0abd-9000000000-28ff6e481b250f18da422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 40V, Negative-QTOFsplash10-0596-9000000000-c496220ba1ebcf4b58f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 10V, Positive-QTOFsplash10-014j-9700000000-e64da48f7f48f62cd9952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 20V, Positive-QTOFsplash10-066v-9000000000-f4dc222564aa0e7745382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxoadipic acid 40V, Positive-QTOFsplash10-0006-9000000000-b5f275a9c00725d5475f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • 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 IDNot Available
Good Scents IDrw1192791
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 ]