P. aeruginosa Metabolome Database: Oxalacetic acid (PAMDB000092)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000092

Identification

Name:

Oxalacetic acid

Description:

Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionized form of oxaloacetic acid) is formed by the oxidation of L-malate, catalyzed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalyzed by citrate synthase.(wikipedia) A class of ketodicarboxylic acids derived from oxalic acid. Oxaloacetic acid is an intermediate in the citric acid cycle and is converted to aspartic acidD by a transamination reaction.

Structure

🔍MOL SDF PDB SMILES InChI View 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
Keto-oxaloacetate
Keto-oxaloacetic acid
Ketosuccinate
Ketosuccinic acid
OAA
Oxalacetate
Oxalacetic acid
Oxaloacetate
Oxaloacetic acid
Oxaloethanoate
Oxaloethanoic acid
Oxosuccinate
Oxosuccinic acid
α-Ketosuccinate
α-Ketosuccinic acid

Chemical Formula:

C₄H₄O₅

Average Molecular Weight:

132.0716

Monoisotopic Molecular Weight:

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)

CAS number:

328-42-7

IUPAC Name:

2-oxobutanedioic acid

Traditional IUPAC Name:

oxalacetate

SMILES:

OC(=O)CC(=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound 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

Short-chain keto acid
Beta-keto acid
1,3-dicarbonyl compound
Dicarboxylic acid or derivatives
Beta-hydroxy ketone
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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:

-2

Melting point:

161 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	134 mg/mL [HMP experimental]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	57.1 mg/mL	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:

Cytoplasm

Reactions:

Citric acid <> Acetic acid + Oxalacetic acid
Tartaric acid <> Water + Oxalacetic acid
Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion
alpha-Ketoglutarate + L-Aspartic acid <> L-Glutamate + Oxalacetic acid
Hydrogen ion + Oxalacetic acid > Carbon dioxide + Pyruvic acid
L-Malic acid + Ubiquinone-8 > Oxalacetic acid + Ubiquinol-8
L-Malic acid + Menaquinone 8 > Menaquinol 8 + Oxalacetic acid
L-Malic acid + NAD <> Hydrogen ion + NADH + Oxalacetic acid
Adenosine triphosphate + Oxalacetic acid <> ADP + Carbon dioxide + Phosphoenolpyruvic acid
Carbon dioxide + Water + Phosphoenolpyruvic acid <> Hydrogen ion + Oxalacetic acid + Phosphate + Hydrogen carbonate
D-tartrate > Water + Oxalacetic acid
Phosphate + Oxalacetic acid <> Water + Phosphoenolpyruvic acid + Carbon dioxide
Citric acid + Coenzyme A <> Acetyl-CoA + Water + Oxalacetic acid
L-Aspartic acid + Water + Oxygen <> Oxalacetic acid + Ammonia + Hydrogen peroxide
Methylcitric acid + Coenzyme A <> Propionyl-CoA + Oxalacetic acid + Water
L-Malic acid + FAD <> FADH2 + Oxalacetic acid
Oxalacetic acid + Water + Propionyl-CoA <> Hydrogen ion + Methylcitric acid + Coenzyme A
L-Aspartic acid + Oxoglutaric acid <> Oxalacetic acid + L-Glutamate

L-Malic acid + a quinone > Oxalacetic acid + a quinol
L-Malic acid + Oxygen <> Oxalacetic acid + Hydrogen peroxide
Oxalacetic acid enol-oxaloacetate
Phosphate + Oxalacetic acid <> Phosphoenolpyruvic acid + Hydrogen carbonate
Pyridoxamine + Oxalacetic acid <> Pyridoxal + L-Aspartic acid
Inorganic phosphate + Oxalacetic acid > Water + Phosphoenolpyruvic acid + Carbonic acid
(3S)-Citryl-CoA > Acetyl-CoA + Oxalacetic acid
L-Malic acid + NAD > Oxalacetic acid + NADH
L-Malic acid + a quinone > Oxalacetic acid + reduced quinone
L-Malic acid + NAD + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADH
L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone
L-Malic acid + NADP + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADPH
L-Malic acid + NAD + L-Malic acid <> Oxalacetic acid + NADH + Hydrogen ion
Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate > Adenosine diphosphate + Phosphate + Oxalacetic acid + ADP
L-Malic acid + Quinone + L-Malic acid > Oxalacetic acid + Hydroquinone
L-Aspartic acid + Oxoglutaric acid + L-Aspartic acid > Oxalacetic acid + L-Glutamic acid + L-Glutamate
L-Aspartic acid + Water + Oxygen + L-Aspartic acid > Oxalacetic acid + Ammonia + Hydrogen peroxide
Oxalacetic acid + Adenosine triphosphate > Adenosine diphosphate + Carbon dioxide + Phosphoenolpyruvic acid + ADP
Propionyl-CoA + Water + Oxalacetic acid + Propionyl-CoA > Coenzyme A + Hydrogen ion + 2-Methylcitric acid + Methylcitric acid

More...

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Arginine and proline metabolism pae00330
Benzoate degradation via hydroxylation pae00362
Carbon fixation in photosynthetic organisms pae00710
Citrate cycle (TCA cycle) pae00020
Cysteine and methionine metabolism pae00270
Glycolysis / Gluconeogenesis pae00010
Glyoxylate and dicarboxylate metabolism pae00630
Isoquinoline alkaloid biosynthesis pae00950
Metabolic pathways pae01100
Methane metabolism pae00680
Microbial metabolism in diverse environments pae01120
Novobiocin biosynthesis pae00401
Phenylalanine metabolism pae00360
Phenylalanine, tyrosine and tryptophan biosynthesis pae00400
Propanoate metabolism pae00640
Pyruvate metabolism pae00620
Reductive carboxylate cycle (CO2 fixation) pae00720
Tropane, piperidine and pyridine alkaloid biosynthesis pae00960
Two-component system pae02020
Tyrosine metabolism pae00350

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-00dr-4900000000-9d943d40beaca3c602a1	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-007a-9210000000-020f60717e2ea79d1ccd	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-000b-9540000000-a53f674cc98960834f88	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-001a-8940000000-40b790e06141d7180938	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-0be675f3aa3e973393b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000f-9000000000-4fba97fcd7b0f2215f75	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-9b1f4171aee6283a3cbd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3900000000-6f4e965a3f513bf8db13	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9600000000-8ae7abf60057088e14db	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-9100000000-5724c215c46a4f568140	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-8900000000-829898d0849b1fbf1c28	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-5a5ff8fb7cb52eebf0c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-657d1384d478ddc33b6d	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f371299a07d43c23ff1d	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Allen RH, Stabler SP, Savage DG, Lindenbaum J: Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency. Metabolism. 1993 Aug;42(8):978-88. Pubmed: 8345822
Dworzak E, Grunicke H, Berger H, Jarosch E, Haas H, Hopfel I: [Pyruvate dehydrogenase deficiency in a child with persistent lactic acidosis] J Clin Chem Clin Biochem. 1985 Jun;23(6):323-9. Pubmed: 3926941
Efimov AS, Gulyi MF, Shcherbak AV, Dzvonkevich ND: [Levels of Krebs cycle metabolites in the blood and urine of patients with diabetes mellitus] Probl Endokrinol (Mosk). 1983 Mar-Apr;29(2):10-4. Pubmed: 6856592
el-Sharabasy MM: Observations on calcium oxalate stone formers. Br J Urol. 1992 Nov;70(5):474-7. Pubmed: 1361403
Esenmo E, Chandramouli V, Schumann WC, Kumaran K, Wahren J, Landau BR: Use of 14CO2 in estimating rates of hepatic gluconeogenesis. Am J Physiol. 1992 Jul;263(1 Pt 1):E36-41. Pubmed: 1322046
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Koike K, Koike M: Fluorescent analysis of alpha-keto acids in serum and urine by high-performance liquid chromatography. Anal Biochem. 1984 Sep;141(2):481-7. Pubmed: 6437276
Olubuyide IO, Festing MF, Chapman C, Higginson J, Whicher JT: Discriminant analysis of biochemical parameters in liver disease. Trop Gastroenterol. 1997 Jan-Mar;18(1):15-9. Pubmed: 9197166
Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23. Pubmed: 15158257
Petrarulo M, Facchini P, Cerelli E, Marangella M, Linari F: Citrate in urine determined with a new citrate lyase method. Clin Chem. 1995 Oct;41(10):1518-21. Pubmed: 7586527
Rabinovich PD, Miliushkin PV: [Content of biological oxidation metabolites in the blood and urine of peptic ulcer patients] Vopr Med Khim. 1979 Nov-Dec;25(6):755-8. Pubmed: 516538
Schauenstein E, Kronberger L, Schaur RJ, Fink E, Georgiopulos E: [Malate and oxaloacetate levels in whole blood of patients with and without malignant tumor diseases] Wien Klin Wochenschr. 1973 Jun 29;85(26):478-82. Pubmed: 4717666
Sperl W, Maurer H, Dworschak E, Hopfel I, Hammerer I: [Lactic acid acidosis with mitochondrial myopathy due to a pyruvate dehydrogenase deficiency] Padiatr Padol. 1985;20(1):55-67. Pubmed: 3919358
Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Wong LT, Davidson AG, Applegarth DA, Dimmick JE, Norman MG, Toone JR, Pirie G, Wong J: Biochemical and histologic pathology in an infant with cross-reacting material (negative) pyruvate carboxylase deficiency. Pediatr Res. 1986 Mar;20(3):274-9. Pubmed: 3085060
Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834

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.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16452
HMDB ID	HMDB00223
Pubchem Compound ID	970
Kegg ID	C00036
ChemSpider ID	945
Wikipedia	Oxalacetic acid
BioCyc ID	OXALACETIC_ACID
EcoCyc ID	OXALACETIC_ACID
Ligand Expo	OAA

Oxalacetic acid (PAMDB000092)

Structure for Oxalacetic acid (PAMDB000092)