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Showing Compound 2-Oxohexanedioic acid (FDB003362)

Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2020-09-17 15:38:29 UTC
Primary IDFDB003362
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Oxohexanedioic acid
DescriptionOxoadipic acid, also known as 2-oxoadipate or a-ketoadipate, 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. Oxoadipic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oxoadipic acid exists in all living species, ranging from bacteria to humans. Within humans, oxoadipic acid participates in a number of enzymatic reactions. In particular, oxoadipic acid and L-glutamic acid can be biosynthesized from aminoadipic acid and oxoglutaric acid through its interaction with the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In addition, oxoadipic acid can be converted into carbon dioxide through the action of the enzyme oxoglutarate dehydrogenase complex. In humans, oxoadipic acid is involved in the metabolic disorder called 2-aminoadipic 2-oxoadipic aciduria. Outside of the human body, Oxoadipic acid has been detected, but not quantified in, pulses. This could make oxoadipic acid a potential biomarker for the consumption of these foods. Oxoadipic acid is a potentially toxic compound. Oxoadipic acid, with regard to humans, has been linked to several inborn metabolic disorders including 2-aminoadipic aciduria, alpha-aminoadipic aciduria, and 2-ketoadipic acidemia. An oxo dicarboxylic acid that is adipic acid substituted by an oxo group at position 2.
CAS Number3184-35-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-OxoadipateChEBI
2-Oxoadipic acidKegg
OxoadipateGenerator
2-Keto-adipateHMDB
2-KetoadipateHMDB
2-Ketoadipic acidHMDB
2-oxo-HexanedioateHMDB
2-oxo-Hexanedioic acidHMDB
2-OxohexanedioateHMDB
2-Oxohexanedioic acidHMDB
2-Oxohexanedionic acidHMDB
a-KetoadipateHMDB
a-Ketoadipic acidHMDB
a-OxoadipateHMDB
a-Oxoadipic acidHMDB
alpha-KetoadipateHMDB
alpha-Ketoadipic acidHMDB
alpha-OxoadipateHMDB
alpha-Oxoadipic acidHMDB
α-Ketoadipic acidHMDB
α-Oxoadipic acidHMDB
2-keto-adipatebiospider
2-ketoadipatebiospider
2-Oxo-hexanedioatebiospider
2-Oxo-hexanedioic acidbiospider
2-oxoadipatebiospider
2-oxohexanedionic acidbiospider
2K-ADIPATEbiospider
A-ketoadipatebiospider
A-ketoadipic acidbiospider
A-oxoadipatebiospider
A-oxoadipic acidbiospider
Alpha-ketoadipatebiospider
Alpha-ketoadipic acidbiospider
Alpha-ketodipatebiospider
Alpha-oxoadipatebiospider
Alpha-oxoadipic acidbiospider
hexanedioic acid, 2-oxo-biospider
Hexanedioic acid, 2-oxo- (7CI,8CI,9CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility23.4 g/LALOGPS
logP-0.37ALOGPS
logP0.34ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity33.48 m³·mol⁻¹ChemAxon
Polarizability14.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H8O5
IUPAC name2-oxohexanedioic acid
InChI IdentifierInChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChI KeyFGSBNBBHOZHUBO-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCC(=O)C(O)=O
Average Molecular Weight160.1247
Monoisotopic Molecular Weight160.037173366
Classification
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
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-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 effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 45.01%; H 5.04%; O 49.96%DFC
Melting PointMp 127°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-002b-3910000000-66f39a8b247786a425e6Spectrum
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-002k-3910000000-977efef811bb47535b80Spectrum
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-0eb27647b831277a2aefSpectrum
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-46cd4d782e3d19030993Spectrum
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-002b-3910000000-66f39a8b247786a425e6Spectrum
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-002k-3910000000-977efef811bb47535b80Spectrum
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-0eb27647b831277a2aefSpectrum
GC-MS2-Oxohexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-46cd4d782e3d19030993Spectrum
Predicted GC-MS2-Oxohexanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r6-9300000000-b3f156c173adabf3f1bbSpectrum
Predicted GC-MS2-Oxohexanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9830000000-a3b1d5e6d378582a6fc2Spectrum
Predicted GC-MS2-Oxohexanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxohexanedioic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-aef94cc19e461712a0972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0bt9-9500000000-9326906313591bb9da1c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-05db676896bb1e3504972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-1e566f572b14692461f22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-527da1c1c271db4d8db42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-9600000000-38ade0e080ecb7a895882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-ea231700b469554fcdb42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9300000000-d69c9552085fc7db91fc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-052f-9000000000-fa207039b6913600e1b42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-dc580b3d8a9e58ea79c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9200000000-f25470d83f4df952958e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c524dfcde428d896e0412021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3e6aec4efdb02abcf8872021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-757eb57780db9df4f78d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016v-9700000000-675e5732632f0a0cabe12015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1da8154067fdb9a274592015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-0e26a52af95eb287809d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066v-7900000000-d898e0593464c13b3f892015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9100000000-34782bad1c8755ac897d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014v-9800000000-1b44ce4709a42734f3842021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9000000000-e16740a0d326b489193c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-99207abec9ffe380ff342021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0295-5900000000-d4320b8980ff5d5a03d32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-9100000000-27e2c4cbbb4945978dc12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-bc42e02ad867f6ce85a42021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)Spectrum
ChemSpider ID70
ChEMBL IDNot Available
KEGG Compound IDC00322
Pubchem Compound ID71
Pubchem Substance IDNot Available
ChEBI ID15753
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00225
CRC / DFC (Dictionary of Food Compounds) IDCWH34-N:CWH34-N
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1485244
KNApSAcK IDC00000770
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
2-oxoglutarate dehydrogenase, mitochondrialOGDHQ02218
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADATQ8N5Z0
Pathways
NameSMPDB LinkKEGG Link
Lysine DegradationSMP00037 map00310
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference