Showing metabocard for Oxoadipic acid (BMDB0000225)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:02 UTC
Update Date2020-05-21 16:28:33 UTC
BMDB IDBMDB0000225
Secondary Accession Numbers
  • BMDB00225
Metabolite Identification
Common NameOxoadipic acid
DescriptionOxoadipic acid, also known as Oxoadipic acid or oxoadipic acid, 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oxoadipic acid exists in all living species, ranging from bacteria to humans. Oxoadipic acid participates in a number of enzymatic reactions, within cattle. In particular, Oxoadipic acid and L-glutamic acid can be biosynthesized from aminoadipic acid and oxoglutaric acid; which is catalyzed by the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In addition, Oxoadipic acid can be converted into carbon dioxide through its interaction with the enzyme oxoglutarate dehydrogenase complex. In cattle, oxoadipic acid is involved in the metabolic pathway called the lysine degradation pathway. Oxoadipic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC6H8O5
Average Molecular Weight160.1247
Monoisotopic Molecular Weight160.037173366
IUPAC Name2-oxohexanedioic acid
Traditional Nameoxoadipate
CAS Registry Number3184-35-8
SMILES
OC(=O)CCCC(=O)C(O)=O
InChI Identifier
InChI=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
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
  • 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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point127 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000225
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003362
KNApSAcK IDC00000770
Chemspider ID70
KEGG Compound IDC00322
BioCyc ID2K-ADIPATE
BiGG ID1485244
Wikipedia LinkNot Available
METLIN ID5234
PubChem Compound71
PDB IDNot Available
ChEBI ID15753
References
Synthesis ReferenceNelson, Randall B.; Gribble, Gordon W. Preparation of a-ketoadipic acid. Organic Preparations and Procedures International (1973), 5(2), 55-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial
General function:
Transcription
Specific function:
Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro) (By similarity).
Gene Name:
AADAT
Uniprot ID:
Q5E9N4
Molecular weight:
47901.0
Reactions
Aminoadipic acid + Oxoglutaric acid → Oxoadipic acid + L-Glutamic aciddetails
Enzyme Details
2. Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial
General function:
Energy production and conversion
Specific function:
Dihydrolipoamide succinyltransferase (E2) component of the 2-oxoglutarate dehydrogenase complex (By similarity). The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2) (By similarity). The 2-oxoglutarate dehydrogenase complex is mainly active in the mitochondrion. A fraction of the 2-oxoglutarate dehydrogenase complex also localizes in the nucleus and is required for lysine succinylation of histones: associates with KAT2A on chromatin and provides succinyl-CoA to histone succinyltransferase KAT2A (By similarity).
Gene Name:
DLST
Uniprot ID:
P11179
Molecular weight:
48973.0
Reactions
Oxoadipic acid + Coenzyme A → Glutaryl-CoA + Carbon dioxidedetails
Enzyme Details
3. 2-oxoglutarate dehydrogenase, mitochondrial
General function:
Energy production and conversion
Specific function:
2-oxoglutarate dehydrogenase (E1) component of the 2-oxoglutarate dehydrogenase complex, which mediates the decarboxylation of alpha-ketoglutarate. The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). The 2-oxoglutarate dehydrogenase complex is mainly active in the mitochondrion. A fraction of the 2-oxoglutarate dehydrogenase complex also localizes in the nucleus and is required for lysine succinylation of histones: associates with KAT2A on chromatin and provides succinyl-CoA to histone succinyltransferase KAT2A.
Gene Name:
OGDH
Uniprot ID:
Q148N0
Molecular weight:
115808.0
Reactions
Oxoadipic acid + Coenzyme A → Glutaryl-CoA + Carbon dioxidedetails
Enzyme Details
4. Dihydrolipoyl dehydrogenase
General function:
Not Available
Specific function:
Not Available
Gene Name:
DLD
Uniprot ID:
F1N206
Molecular weight:
54187.0
Reactions
Oxoadipic acid + Coenzyme A → Glutaryl-CoA + Carbon dioxidedetails