alpha-Ketoisocaproic acid

α-Ketoisocaproic acid
Names

IUPAC name 4-Methyl-2-oxopentanoic acid
Systematic IUPAC name 4-Methyl-2-oxopentanoic acid^[1]
Other names 4-Methyl-2-oxovaleric acid
Identifiers
3DMet	B00066
Beilstein Reference	1701823
CAS Registry Number	816-66-0^Y
ChEBI	CHEBI:48430
ChEMBL	ChEMBL445647^Y
ChemSpider	69^Y
DrugBank	DB03229
EC number	212-435-5
InChI InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)^Y Key: BKAJNAXTPSGJCU-UHFFFAOYSA-N^Y InChI=1/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9) Key: BKAJNAXTPSGJCU-UHFFFAOYAG
Jmol-3D images	Image Image
KEGG	C00233^Y
MeSH	Alpha-ketoisocaproic+acid
PubChem	70
SMILES CC(C)CC(=O)C(O)=O O=C(C(=O)O)CC(C)C
UN number	3265
Properties
Molecular formula	C₆H₁₀O₃
Molar mass	130.14 g·mol⁻¹
Density	1.055 g cm⁻³ (at 20 °C)
Melting point	8 °C (46 °F; 281 K)
Boiling point	85 °C (185 °F; 358 K) at 13 mmHg
log P	0.133
Acidity (pK_a)	2.651
Basicity (pK_b)	11.346
Hazards
EU classification	C
R-phrases	R34
S-phrases	S26, S36/37/39, S45
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

α-Ketoisocaproic acid is an intermediate in the metabolism of leucine.

References

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Agmatine Ornithine Cadaverine Putrescine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

Other

Cysteine metabolism	Cysteine sulfinic acid

Index of inborn errors of metabolism

Description	Metabolism Enzymes and pathways: citric acid cycle enzymes pentose phosphate intermediates glycoproteins enzymes glycosaminoglycans proteoglycan enzymes phospholipid metabolism cholesterol and steroid intermediates sphingolipids enzymes eicosanoids enzymes amino acid intermediates urea cycle enzymes nucleotide intermediates

Disorders	Citric acid cycle and electron transport chain Glycoprotein Proteoglycan Fatty-acid Phospholipid Cholesterol and steroid Eicosanoid Amino acid Purine-pyrimidine Heme metabolism Symptoms and signs

Treatment	Drugs other

Index of biochemical families

Carbohydrates	Alcohols Glycoproteins Glycosides

Lipids	Eicosanoids Fatty acids intermediates Glycerides Phospholipids Sphingolipids Steroids

Nucleic acids	Constituents intermediates

Proteins	Amino acids intermediates

Other	Tetrapyrroles intermediates