Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2019-11-26 02:59:02 UTC
Primary IDFDB003362
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Oxohexanedioic acid
DescriptionPresent in pea seedlings 2-Oxoadipic acid is produced from lysine in the cytosol of cells via the saccharopine and the pipecolic acid pathways. Catabolites of hydroxylysine and tryptophan enter these pathways as 2-aminoadipic- -semialdehyde and 2-oxoadipate, respectively. In the matrix of mitochondria, 2-oxoadipate is decarboxylated to glutaryl-CoA by the 2-oxoadipate dehydrogenase complex and then converted to acetyl-CoA.; 2-Oxoadipic aciduria is an in-born error of metabolism of lysine, tryptophan, and hydroxylysine, in which abnormal quantities of 2-aminoadipic acid are found in body fluids along with 2-oxoadipic acid. Patients with ; 2-Oxoadipic acidemias are mentally retarded with hypotonia or seizures. 2-Oxoadipic Aciduria can occur in patients with Kearns-Sayre Syndrome, a progressive disorder with onset prior to 20 years of age in which multiple organ systems are affected, including progressive external ophthalmoplegia, retinopathy, and the age of onset, and these are associated classically with abnormalities in cardiac conduction, cerebellar signs, and elevated cerebrospinal fluid protein. (PMID: 10655159, 16183823, 11083877).
CAS Number3184-35-8
Structure
Thumb
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 - Experimental
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002b-3910000000-66f39a8b247786a425e6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002k-3910000000-977efef811bb47535b80JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-6900000000-0eb27647b831277a2aefJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-6900000000-46cd4d782e3d19030993JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002b-3910000000-66f39a8b247786a425e6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002k-3910000000-977efef811bb47535b80JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-6900000000-0eb27647b831277a2aefJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-6900000000-46cd4d782e3d19030993JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r6-9300000000-b3f156c173adabf3f1bbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-9830000000-a3b1d5e6d378582a6fc2JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-aef94cc19e461712a097JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0bt9-9500000000-9326906313591bb9da1cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-05db676896bb1e350497JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-1e566f572b14692461f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-527da1c1c271db4d8db4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-9600000000-38ade0e080ecb7a89588JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-757eb57780db9df4f78dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016v-9700000000-675e5732632f0a0cabe1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1da8154067fdb9a27459JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-0e26a52af95eb287809dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066v-7900000000-d898e0593464c13b3f89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9100000000-34782bad1c8755ac897dJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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