ChemFOnt: Showing chemical card for 4-Hydroxy-2-oxoglutaric acid (CFc000001389)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:00 UTC

Chemfont ID

CFc000001389

Molecule Identification

Common Name

4-Hydroxy-2-oxoglutaric acid

Definition

4-Hydroxy-2-ketoglutaric acid is a substrate for Fructose-bisphosphate aldolase A.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-2-oxoglutarate	Generator
2-Keto-4-hydroxyglutarate	MeSH
2-Keto-4-hydroxyglutarate, (+-)-isomer	MeSH
(+/-)-2-hydroxy-4-oxopentanedioate	HMDB
(+/-)-2-hydroxy-4-oxopentanedioic acid	HMDB
2-Hydroxy-4-oxopentanedioate	HMDB
2-Hydroxy-4-oxopentanedioic acid	HMDB
2-oxo-4-Hydroxyglutarate	HMDB
4-Hydroxy-2-ketoglutarate	HMDB
D-4-Hydroxy-2-ketoglutarate	HMDB

Chemical Formula

C₅H₆O₆

Average Molecular Weight

162.0975

Monoisotopic Molecular Weight

162.016437924

IUPAC Name

2-hydroxy-4-oxopentanedioic acid

Traditional Name

4-hydroxy-2-oxoglutaric acid

CAS Registry Number

1187-99-1

SMILES

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

InChI Identifier

InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)

InChI Key

WXSKVKPSMAHCSG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:30923 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0002070)

Source

Endogenous

Endogenous (HMDB: HMDB0002070)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arginine and Proline Metabolism (PathBank: SMP0012004)
Arginine and Proline Metabolism (HMDB: HMDB0002070)

Disease pathway

Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency) (PathBank: SMP0120454)
Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency (PathBank: SMP0120569)
Hyperprolinemia Type I (PathBank: SMP0120719)
Hyperornithinemia with Gyrate Atrophy (HOGA) (PathBank: SMP0120789)
Hyperprolinemia Type II (PathBank: SMP0120501)
Prolinemia Type II (PathBank: SMP0120539)
Prolidase Deficiency (PD) (PathBank: SMP0120541)
L-Arginine:Glycine Amidinotransferase Deficiency (PathBank: SMP0120572)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0120790)
Ornithine Aminotransferase Deficiency (OAT Deficiency) (PathBank: SMP0120538)
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) (PathBank: SMP0120710)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0000506)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	69.8 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.82	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Acidic)	2.45	ChemAxon
pKa (Strongest Basic)	-3.9	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	4	ChemAxon
Refractivity	30.22 m³·mol⁻¹	ChemAxon
Polarizability	12.76 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon