P. aeruginosa Metabolome Database: Oxalosuccinic acid (PAMDB000548)

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

PAMDB000548

Identification

Name:

Oxalosuccinic acid

Description:

Oxalosuccinate is a substrate for cytoplasmic Isocitrate dehydrogenase and mitochondiral Isocitrate dehydrogenase (mitochondrial).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Oxalo-succ
Oxalosuccinate
Oxalosuccinic acid

Chemical Formula:

C₆H₆O₇

Average Molecular Weight:

190.1076

Monoisotopic Molecular Weight:

190.011352546

InChI Key:

UFSCUAXLTRFIDC-UHFFFAOYSA-N

InChI:

InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)

CAS number:

1948-82-9

IUPAC Name:

1-oxopropane-1,2,3-tricarboxylic acid

Traditional IUPAC Name:

oxalosuccinate

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Gamma-keto acid
Beta-keto acid
1,3-dicarbonyl compound
Keto acid
Beta-hydroxy ketone
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	7.47 mg/mL	ALOGPS
logP	-0.55	ALOGPS
logP	-0.37	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	-10	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.17 m³·mol^-1	ChemAxon
Polarizability	14.95 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:

Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide
Isocitric acid + NADP <> Oxalosuccinic acid + NADPH + Hydrogen ion
Oxalosuccinic acid + Hydrogen ion > Oxoglutaric acid + Carbon dioxide
Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion

Pathways:

Citrate cycle (TCA cycle) pae00020
Glutathione metabolism pae00480
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Reductive carboxylate cycle (CO2 fixation) pae00720

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dj-1900000000-ed9f625da4af156fd85a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-8900000000-b245ec6d4dca3949083d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9300000000-00b8a65afa1e83c61b5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000b-0900000000-a6734cca6590d164a554	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-3900000000-c30d22d22f12460fcc5c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dj-9300000000-a3b40df9f3852aa0e3c8	View in MoNA

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

Synthesis Reference:

Takeda, Isao; Iguchi, Takashi. Fermentative production of oxalosuccinic acid from hydrocarbons. Jpn. Tokkyo Koho (1972), 3 pp.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	7815
HMDB ID	HMDB03974
Pubchem Compound ID	972
Kegg ID	C05379
ChemSpider ID	947
Wikipedia	Oxalosuccinic_acid
BioCyc ID	OXALO-SUCCINATE
EcoCyc ID	OXALO-SUCCINATE

Oxalosuccinic acid (PAMDB000548)

Structure for Oxalosuccinic acid (PAMDB000548)