Oxalacetic acid (YMDB00235)

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Identification

YMDB ID

YMDB00235

Name

Oxalacetic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Oxalacetic acid, also known as oxaloacetate or 2-oxosuccinate, 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. Oxalacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oxalacetic acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 number

328-42-7

Weight

Average: 132.0716
Monoisotopic: 132.005873238

InChI Key

KHPXUQMNIQBQEV-UHFFFAOYSA-N

InChI

InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)

IUPAC Name

2-oxobutanedioic acid

Traditional IUPAC Name

oxalacetate

Chemical Formula

C₄H₄O₅

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-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 Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:30744 )
oxo dicarboxylic acid (CHEBI:30744 )
Dicarboxylic acids (LMFA01170120 )

Physical Properties

State

Solid

Charge

Melting point

161 °C

Experimental Properties

Property	Value	Reference
Water Solubility	134 mg/mL [HMP experimental]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	57.1 g/L	ALOGPS
logP	-0.68	ALOGPS
logP	-0.042	ChemAxon
logS	-0.36	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	-9.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	24.33 m³·mol⁻¹	ChemAxon
Polarizability	10.06 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
mitochondrion
peroxisome
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Asparagine metabolism	PW002274
Aspartate metabolism	PW002375
Citric Acid Cycle	PW000952
Citric Acid Cycle 1434561204	PW000970
Glyoxylate cycle	PW002419

KEGG Pathways

Alanine, aspartate and glutamate metabolism	ec00250
Citrate cycle (TCA cycle)	ec00020
Glycolysis / Gluconeogenesis	ec00010
Glyoxylate and dicarboxylate metabolism	ec00630
Methane metabolism	ec00680

SMPDB Reactions

Acetyl-CoA + water + Oxalacetic acid → Citric acid + Coenzyme A

(S)-Malic acid + NAD ↔ Oxalacetic acid + NADH + hydron

Oxalacetic acid + hydron + NADH → (S)-Malic acid + NAD

Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate → ADP + phosphate + Oxalacetic acid

NADH + hydron + Oxalacetic acid ← (S)-Malic acid + NAD

KEGG Reactions

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
25 ± 25 µM	Minimal medium supplemented with ammonia salts and (glucose or galactose)	aerobic;growing cells	Baker's yeast	PMID: 4578278
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00dr-4900000000-9d943d40beaca3c602a1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-007a-9210000000-020f60717e2ea79d1ccd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-000b-9540000000-a53f674cc98960834f88	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-001a-8940000000-40b790e06141d7180938	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-007a-9210000000-020f60717e2ea79d1ccd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000b-9540000000-a53f674cc98960834f88	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001a-8940000000-40b790e06141d7180938	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-4930000000-7e995327b0b9c1af0914	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-6718417e7196063f9544	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ds-9520000000-5a082ec8843f6fbc3b15	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-0be675f3aa3e973393b7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000f-9000000000-4fba97fcd7b0f2215f75	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-9b1f4171aee6283a3cbd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-014i-0900000000-7c598fd9c78acb94dacd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-014i-4900000000-e7803730ae7986a1b9fb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-014r-5900000000-8e478338a7c0e65e62ba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014r-7900000000-f681763317e1ae86e691	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-00kr-9600000000-aa8adf9a96041dddbbdd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-000i-9200000000-e62c47ca2bc492900178	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-000i-9000000000-5485ddd84a64ea0ca0b9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-000i-9000000000-79521cb04a2b23e39c1e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-000m-9000000000-601c8d2ec63f8b01a61e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-000e-9000000000-13d369c58d8930958d92	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0005-9000000000-df8387ef907fb71342eb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0005-9000000000-908644b5d7041346f582	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0005-9000000000-ecca787a800164d0296f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0005-9000000000-180a7c51b1f93cb8fff2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0005-9000000000-709c49f609f5a711a288	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0005-9000000000-aa103ab9beb03bd6eb22	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3900000000-6f4e965a3f513bf8db13	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9600000000-8ae7abf60057088e14db	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-9100000000-5724c215c46a4f568140	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-8900000000-829898d0849b1fbf1c28	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-5a5ff8fb7cb52eebf0c8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-657d1384d478ddc33b6d	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f371299a07d43c23ff1d	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	30744
HMDB ID	HMDB00223
Pubchem Compound ID	970
Kegg ID	C00036
ChemSpider ID	945
FOODB ID	FDB031075
Wikipedia	Oxaloacetic_acid
BioCyc ID	OXALACETIC_ACID

Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
propanoyl-CoA + H2O + oxaloacetate → (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA

ATP + acetyl-CoA + HCO(3)(-) → ADP + phosphate + malonyl-CoA.
ATP + biotin-[carboxyl-carrier-protein] + CO(2) → ADP + phosphate + carboxy-biotin-[carboxyl-carrier-protein].

Structure for #<Compound:0xadfc1c70>

Enzymes

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