ECMDB: 2-Hydroxy-3-oxosuccinate (ECMDB04080) (M2MDB000598)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (133)

Record Information

Version

2.0

Creation Date

2012-05-31 14:04:20 -0600

Update Date

2015-06-03 15:54:42 -0600

Secondary Accession Numbers

ECMDB04080

Identification

Name:

2-Hydroxy-3-oxosuccinate

Description

2-hydroxy-3-oxosuccinate is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. 2-hydroxy-3-oxosuccinate is invovled in Glyoxylate and dicarboxylate metabolism. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Hydroxy-3-oxosuccinic acid
Oxaloglycolate
Oxaloglycolic acid

Chemical Formula:

C₄H₄O₆

Weight:

Average: 148.071
Monoisotopic: 148.00078786

InChI Key:

RMHHUKGVZFVHED-UHFFFAOYSA-N

InChI:

InChI=1S/C4H4O6/c5-1(3(7)8)2(6)4(9)10/h1,5H,(H,7,8)(H,9,10)

CAS number:

Not Available

IUPAC Name:

2-hydroxy-3-oxobutanedioic acid

Traditional IUPAC Name:

oxaloglycolate

SMILES:

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

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

Short-chain keto acid
Beta-hydroxy acid
Beta-keto acid
Acyloin
Alpha-hydroxy acid
Alpha-keto acid
1,3-dicarbonyl compound
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Beta-hydroxy ketone
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:17778 )
oxo dicarboxylic acid (CHEBI:17778 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	36.2 g/L	ALOGPS
logP	-0.84	ALOGPS
logP	-0.76	ChemAxon
logS	-0.61	ALOGPS
pKa (Strongest Acidic)	2.12	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	25.67 m³·mol⁻¹	ChemAxon
Polarizability	10.95 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:

Meso-Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion
Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion

SMPDB Pathways:

glycolate and glyoxylate degradation II

PW002021

KEGG Pathways:

Butanoate metabolism ec00650
Glyoxylate and dicarboxylate metabolism ec00630

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9200000000-cd740f7e698301d2bbd3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0900000000-e5e138e6e0d0007bf55b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pc1-6900000000-20b68b190053ee432e0c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-5d262ada67f1c3e91286	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fdk-4900000000-c122d4dc634dd6e7f216	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-8900000000-57efe7b6930de7669a6e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-6cf676ace412f8964d70	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17778
HMDB ID	HMDB0149325
Pubchem Compound ID	524
Kegg ID	C03459
ChemSpider ID	509
Wikipedia ID	Not Available
BioCyc ID	CPD-66
EcoCyc ID	CPD-66

Enzymes

Protein Details

1. D-malate dehydrogenase [decarboxylating]

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the NAD(+)-dependent oxidative decarboxylation of D-malate into pyruvate. Is essential for aerobic growth on D- malate as the sole carbon source. But is not required for anaerobic D-malate utilization, although DmlA is expressed and active in those conditions. Appears to be not able to use L- tartrate as a substrate for dehydrogenation instead of D-malate
Gene Name:: dmlA
Uniprot ID:: P76251
Molecular weight:: 40315

Reactions

(R)-malate + NAD(+) = pyruvate + CO(2) + NADH.

2-Hydroxy-3-oxosuccinate (ECMDB04080) (M2MDB000598)

Structure for #<Compound:0xae506a14>

Enzymes

Reactions