ChemFOnt: Showing chemical card for 2-Methyl-3-ketovaleric acid (CFc000000307)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:40 UTC

Chemfont ID

CFc000000307

Molecule Identification

Common Name

2-Methyl-3-ketovaleric acid

Definition

2-Methyl-3-ketovaleric acid is a metabolite of beta-leucine in the beta-keto pathway of leucine metabolism. 2-Methyl-3-ketovaleric acid is a known pathological metabolite and associated with propionic acidemia, especially during periods of ketoacidosis; a severe deficiency of propionyl-CoA carboxylase in cultured fibroblasts has been detected in some neonatal cases. (PMID 7389125 , 6820422 , 7119896 , 7430116 , 3356699 ). 2-Methyl-3-ketovaleric acid induces a strong activity of inosine-5'-monophosphate dehydrogenase (IMPDH; the rate-limiting enzyme in GTP synthesis), mimicking glucose. (PMID: 11145582 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyl-3-oxo-pentanoic acid	ChEBI
2-Methyl-3-oxovaleric acid	ChEBI
beta-Ketoisocaproic acid	ChEBI
2-Methyl-3-oxo-pentanoate	Generator
2-Methyl-3-oxovalerate	Generator
b-Ketoisocaproate	Generator
b-Ketoisocaproic acid	Generator
beta-Ketoisocaproate	Generator
Β-ketoisocaproate	Generator
Β-ketoisocaproic acid	Generator
2-Methyl-3-ketovalerate	Generator

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

2-methyl-3-oxopentanoic acid

Traditional Name

2-methyl-3-oxovaleric acid

CAS Registry Number

14925-93-0

SMILES

CCC(=O)C(C)C(O)=O

InChI Identifier

InChI=1S/C6H10O3/c1-3-5(7)4(2)6(8)9/h4H,3H2,1-2H3,(H,8,9)

InChI Key

QTLYPQZWYOHATR-UHFFFAOYSA-N

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
Branched fatty acid
Methyl-branched fatty acid
Short-chain keto acid
Beta-hydroxy ketone
Fatty acyl
1,3-dicarbonyl compound
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-oxo monocarboxylic acid (CHEBI:86365 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 21389975)

Source

Endogenous

Endogenous (HMDB: HMDB0000408)

Exogenous

Food

Food (HMDB: HMDB0000408)

Animal origin

Poultry

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)

Exogenous (HMDB: HMDB0000408)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0000408)

Role

Biological role

Energy source (HMDB: HMDB0000408)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000408)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	60.6 g/L	ALOGPS
logP	0.72	ALOGPS
logP	1.24	ChemAxon
logS	-0.33	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.74 m³·mol⁻¹	ChemAxon
Polarizability	12.95 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

External Links

HMDB ID

HMDB0000408

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022024

KNApSAcK ID

C00052124

Chemspider ID

164251

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5397

PubChem Compound

189028

PDB ID

Not Available

ChEBI ID

86365

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Hirai, Yasuhiro; Aida, Takuzo; Inoue, Shohei. Artificial photosynthesis of b-ketocarboxylic acids from carbon dioxide and ketones via enolate complexes of aluminum porphyrin. , Journal of the American Chemical Society (1989), 111(8), 3062-3.

Showing chemical card for 2-Methyl-3-ketovaleric acid (CFc000000307)

MOL for CFc000000307 (2-Methyl-3-ketovaleric acid)

3D MOL for CFc000000307 (2-Methyl-3-ketovaleric acid)

3D SDF for CFc000000307 (2-Methyl-3-ketovaleric acid)

3D-SDF for CFc000000307 (2-Methyl-3-ketovaleric acid)

PDB for CFc000000307 (2-Methyl-3-ketovaleric acid)

3D PDB for CFc000000307 (2-Methyl-3-ketovaleric acid)

SMILES for CFc000000307 (2-Methyl-3-ketovaleric acid)

INCHI for CFc000000307 (2-Methyl-3-ketovaleric acid)

Structure for CFc000000307 (2-Methyl-3-ketovaleric acid)

3D Structure for CFc000000307 (2-Methyl-3-ketovaleric acid)