Canmetcon
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 IDYMDB00235
NameOxalacetic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionOxaloacetic acid is an intermediate in the citric acid cycle and is converted to aspartic acid by a transamination reaction.
Structure
Thumb
Synonyms
  • 2-Ketosuccinate
  • 2-Ketosuccinic acid
  • 2-Oxobutanedioate
  • 2-Oxobutanedioic acid
  • 2-Oxosuccinate
  • 2-Oxosuccinic acid
  • a-Ketosuccinate
  • a-Ketosuccinic acid
  • alpha-Ketosuccinate
  • alpha-Ketosuccinic acid
  • Ketosuccinate
  • Ketosuccinic acid
  • OAA
  • oxalacetate
  • Oxaloacetate
  • oxaloacetate dianion
  • Oxaloacetic acid
  • Oxaloethanoate
  • Oxaloethanoic acid
  • oxobutanedioate
  • oxobutanedioic acid, ion(2-)
  • Oxosuccinate
  • Oxosuccinic acid
  • 3-Carboxy-3-oxopropanoic acid
  • Keto-succinic acid
  • Oxobutanedioic acid
  • Keto-oxaloacetate
  • 3-Carboxy-3-oxopropanoate
  • Keto-succinate
  • Keto-oxaloacetic acid
  • Acid, oxaloacetic
  • Acid, oxalacetic
  • 2 Ketosuccinic acid
  • 2 oxo Butanedioic acid
  • 2-oxo-Butanedioic acid
CAS number328-42-7
WeightAverage: 132.0716
Monoisotopic: 132.005873238
InChI KeyKHPXUQMNIQBQEV-UHFFFAOYSA-N
InChIInChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
IUPAC Name2-oxobutanedioic acid
Traditional IUPAC Nameoxalacetate
Chemical FormulaC4H4O5
SMILES[H]OC(=O)C(=O)C([H])([H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point161 °C
Experimental Properties
PropertyValueReference
Water Solubility134 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility57.1 g/LALOGPS
logP-0.68ALOGPS
logP-0.042ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.33 m³·mol⁻¹ChemAxon
Polarizability10.06 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • peroxisome
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Asparagine metabolismPW002274 ThumbThumb?image type=greyscaleThumb?image type=simple
Aspartate metabolismPW002375 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Glyoxylate cyclePW002419 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Citrate cycle (TCA cycle)ec00020 Map00020
Glycolysis / Gluconeogenesisec00010 Map00010
Glyoxylate and dicarboxylate metabolismec00630 Map00630
Methane metabolismec00680 Map00680
SMPDB Reactions
Acetyl-CoA + water + Oxalacetic acidCitric acid + Coenzyme A
(S)-Malic acid + NADOxalacetic acid + NADH + hydron
Oxalacetic acid + hydron + NADH(S)-Malic acid + NAD
Adenosine triphosphate + Pyruvic acid + Hydrogen carbonateADP + phosphate + Oxalacetic acid
NADH + hydron + Oxalacetic acid(S)-Malic acid + NAD
KEGG Reactions
propionyl-CoA + water + Oxalacetic acid(2S,3S)-2-Methylcitric acid + hydron + Coenzyme A
L-Aspartic acid + Oxoglutaric acidL-Glutamic acid + Oxalacetic acid
Acetyl-CoA + water + Oxalacetic acidhydron + Citric acid + Coenzyme A
NAD + (S)-malate(2-)NADH + hydron + Oxalacetic acid
Adenosine triphosphate + Oxalacetic acidPhosphoenolpyruvic acid + Carbon dioxide + ADP
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
25 ± 25 µM Minimal medium supplemented with ammonia salts and (glucose or galactose)aerobic;growing cellsBaker's yeastPMID: 4578278
Conversion Details Here
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
  • Luttik, M. A., Kotter, P., Salomons, F. A., van der Klei, I. J., van Dijken, J. P., Pronk, J. T. (2000). "The Saccharomyces cerevisiae ICL2 gene encodes a mitochondrial 2-methylisocitrate lyase involved in propionyl-coenzyme A metabolism." J Bacteriol 182:7007-7013.11092862
  • Przybyla-Zawislak, B., Gadde, D. M., Ducharme, K., McCammon, M. T. (1999). "Genetic and biochemical interactions involving tricarboxylic acid cycle (TCA) function using a collection of mutants defective in all TCA cycle genes." Genetics 152:153-166.10224250
  • Velot, C., Lebreton, S., Morgunov, I., Usher, K. C., Srere, P. A. (1999). "Metabolic effects of mislocalized mitochondrial and peroxisomal citrate synthases in yeast Saccharomyces cerevisiae." Biochemistry 38:16195-16204.10587442
  • Verleur, N., Elgersma, Y., Van Roermund, C. W., Tabak, H. F., Wanders, R. J. (1997). "Cytosolic aspartate aminotransferase encoded by the AAT2 gene is targeted to the peroxisomes in oleate-grown Saccharomyces cerevisiae." Eur J Biochem 247:972-980.9288922
  • Singh, J., Kumar, D., Ramakrishnan, N., Singhal, V., Jervis, J., Garst, J. F., Slaughter, S. M., DeSantis, A. M., Potts, M., Helm, R. F. (2005). "Transcriptional response of Saccharomyces cerevisiae to desiccation and rehydration." Appl Environ Microbiol 71:8752-8763.16332871
  • Jia, Y. K., Becam, A. M., Herbert, C. J. (1997). "The CIT3 gene of Saccharomyces cerevisiae encodes a second mitochondrial isoform of citrate synthase." Mol Microbiol 24:53-59.9140965
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
Synthesis Reference:Heidelberger, Charles; Hurlbert, Robert B. The synthesis of oxalacetic acid-I-C14 and orotic acid-6-C14. Journal of the American Chemical Society (1950), 72 4704-6.
External Links:
ResourceLink
CHEBI ID30744
HMDB IDHMDB00223
Pubchem Compound ID970
Kegg IDC00036
ChemSpider ID945
FOODB IDFDB001479
WikipediaOxaloacetic_acid
BioCyc IDOXALACETIC_ACID

Enzymes

General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
Gene Name:
CIT3
Uniprot ID:
P43635
Molecular weight:
53810.69922
Reactions
Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
propanoyl-CoA + H2O + oxaloacetate → (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
Gene Name:
CIT2
Uniprot ID:
P08679
Molecular weight:
51412.89844
Reactions
Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
Gene Name:
CIT1
Uniprot ID:
P00890
Molecular weight:
53359.60156
Reactions
Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
General function:
Involved in electron carrier activity
Specific function:
Could be a fumarate reductase
Gene Name:
OSM1
Uniprot ID:
P21375
Molecular weight:
55064.80078
Reactions
General function:
Involved in catalytic activity
Specific function:
Exhibits dehydratase activity specific for L-threo-3- hydroxyaspartate
Gene Name:
SRY1
Uniprot ID:
P36007
Molecular weight:
34898.69922
Reactions
Threo-3-hydroxy-L-aspartate → oxaloacetate + NH(3).
General function:
Involved in catalytic activity
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second
Gene Name:
PYC1
Uniprot ID:
P11154
Molecular weight:
130098.0
Reactions
ATP + pyruvate + HCO(3)(-) → ADP + phosphate + oxaloacetate.
General function:
Involved in acetyl-CoA carboxylase activity
Specific function:
Carries out three functions:biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase
Gene Name:
FAS3
Uniprot ID:
Q00955
Molecular weight:
250351.0
Reactions
ATP + acetyl-CoA + HCO(3)(-) → ADP + phosphate + malonyl-CoA.
ATP + biotin-[carboxyl-carrier-protein] + CO(2) → ADP + phosphate + carboxy-biotin-[carboxyl-carrier-protein].
General function:
Involved in phosphoenolpyruvate carboxykinase (ATP) activity
Specific function:
ATP + oxaloacetate = ADP + phosphoenolpyruvate + CO(2)
Gene Name:
PCK1
Uniprot ID:
P10963
Molecular weight:
60982.69922
Reactions
ATP + oxaloacetate → ADP + phosphoenolpyruvate + CO(2).
General function:
Involved in catalytic activity
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second
Gene Name:
PYC2
Uniprot ID:
P32327
Molecular weight:
130166.0
Reactions
ATP + pyruvate + HCO(3)(-) → ADP + phosphate + oxaloacetate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
The isoenzyme MDH2 may function primarily in the glyoxylate cycle
Gene Name:
MDH2
Uniprot ID:
P22133
Molecular weight:
40730.39844
Reactions
(S)-malate + NAD(+) → oxaloacetate + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
(S)-malate + NAD(+) = pyruvate + CO(2) + NADH
Gene Name:
MAE1
Uniprot ID:
P36013
Molecular weight:
74375.29688
Reactions
(S)-malate + NAD(+) → pyruvate + CO(2) + NADH.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
(S)-malate + NAD(+) = oxaloacetate + NADH
Gene Name:
MDH3
Uniprot ID:
P32419
Molecular weight:
37185.89844
Reactions
(S)-malate + NAD(+) → oxaloacetate + NADH.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol
Gene Name:
AAT1
Uniprot ID:
Q01802
Molecular weight:
51795.10156
Reactions
L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism
Gene Name:
AAT2
Uniprot ID:
P23542
Molecular weight:
46057.30078
Reactions
L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
(S)-malate + NAD(+) = oxaloacetate + NADH
Gene Name:
MDH1
Uniprot ID:
P17505
Molecular weight:
35649.60156
Reactions
(S)-malate + NAD(+) → oxaloacetate + NADH.

Transporters

General function:
Involved in binding
Specific function:
Transports oxaloacetate and sulfate
Gene Name:
OAC1
Uniprot ID:
P32332
Molecular weight:
35152.80078