You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00142
NameOxoadipic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Oxoadipic acid is produced from lysine in the cytosol of cells via the saccharopine and the pipecolic acid pathways.
Structure
Thumb
Synonyms
  • 2-keto-adipate
  • 2-ketoadipate
  • 2-Ketoadipic acid
  • 2-Oxo-hexanedioate
  • 2-Oxo-hexanedioic acid
  • 2-oxoadipate
  • 2-Oxoadipic acid
  • 2-Oxohexanedioate
  • 2-Oxohexanedioic acid
  • 2-oxohexanedionic acid
  • a-Ketoadipate
  • a-Ketoadipic acid
  • a-Oxoadipate
  • a-Oxoadipic acid
  • alpha-Ketoadipate
  • alpha-ketoadipic acid
  • alpha-Oxoadipate
  • alpha-Oxoadipic acid
  • Oxoadipate
CAS number3184-35-8
WeightAverage: 160.1247
Monoisotopic: 160.037173366
InChI KeyFGSBNBBHOZHUBO-UHFFFAOYSA-N
InChIInChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
IUPAC Name2-oxohexanedioic acid
Traditional IUPAC Nameoxoadipate
Chemical FormulaC6H8O5
SMILES[H]OC(=O)C(=O)C([H])([H])C([H])([H])C([H])([H])C(=O)O[H]
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
Physical Properties
StateSolid
Charge0
Melting point127 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
lysine metabolismPW002420 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Lysine biosynthesisec00300 Map00300
Lysine degradationec00310 Map00310
Tryptophan metabolismec00380 Map00380
SMPDB Reactions
(1R,2S)-homoisocitrate + NADCarbon dioxide + NADH + Oxoadipic acid
KEGG Reactions
L-Glutamic acid + Oxoadipic acidL-2-aminoadipate + Oxoglutaric acid
2-Oxaloglutaric acid + hydronCarbon dioxide + Oxoadipic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Strassman, M., Ceci, L. N. (1965). "Enzymatic formation of alpha-ketoadipic acid from homoisocitric acid." J Biol Chem 240:4357-4361.4284830
Synthesis Reference:Nelson, Randall B.; Gribble, Gordon W. Preparation of a-ketoadipic acid. Organic Preparations and Procedures International (1973), 5(2), 55-8.
External Links:
ResourceLink
CHEBI ID15753
HMDB IDHMDB00225
Pubchem Compound ID71
Kegg IDC00322
ChemSpider ID70
FOODB IDFDB003362
Wikipedia IDNot Available
BioCyc ID2K-ADIPATE

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the NAD(+)-dependent conversion of homoisocitrate to alpha-ketoadipate
Gene Name:
LYS12
Uniprot ID:
P40495
Molecular weight:
40068.60156
Reactions
(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate + NAD(+) → 2-oxoadipate + CO(2) + NADH.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity. Also active with methionine, alpha-aminoadipate and leucine when phenylpyruvate is the amino acceptor
Gene Name:
ARO8
Uniprot ID:
P53090
Molecular weight:
56177.30078
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate

Transporters

General function:
Involved in transporter activity
Specific function:
Transports C5-C7 oxodicarboxylates across the inner membranes of mitochondria. Can transport 2-oxoadipate, 2- oxoglutarate, adipate, glutarate, 2-oxopimelate, oxaloacetate, citrate and malate. The main physiological role is probably to supply 2-oxoadipate and 2-oxoglutarate from the mitochondrial matrix to the cytosol where they are used in the biosynthesis of lysine and glutamate, respectively, and in lysine catabolism
Gene Name:
ODC2
Uniprot ID:
Q99297
Molecular weight:
34006.69922
General function:
Involved in transporter activity
Specific function:
Transports C5-C7 oxodicarboxylates across the inner membranes of mitochondria. Can transport 2-oxoadipate, 2- oxoglutarate, adipate, glutarate, 2-oxopimelate, oxaloacetate, citrate and malate. The main physiological role is probably to supply 2-oxoadipate and 2-oxoglutarate from the mitochondrial matrix to the cytosol where they are used in the biosynthesis of lysine and glutamate, respectively, and in lysine catabolism
Gene Name:
ODC1
Uniprot ID:
Q03028
Molecular weight:
34206.0