alpha-Ketoisocaproic acid

α-Ketoisocaproic acid

IUPAC name 4-Methyl-2-oxopentanoic acid
Systematic name 4-Methyl-2-oxopentanoic acid^[1]
Other names 4-Methyl-2-oxovaleric acid
Identifiers
CAS number	816-66-0^Y
PubChem	70
ChemSpider	69^Y
EC number	212-435-5
UN number	3265
DrugBank	DB03229
KEGG	C00233^Y
MeSH	Alpha-ketoisocaproic+acid
ChEBI	CHEBI:48430
ChEMBL	CHEMBL445647^Y
Beilstein Reference	1701823
3DMet	B00066
Jmol-3D images	Image 1 Image 2
SMILES CC(C)CC(=O)C(O)=O O=C(C(=O)O)CC(C)C
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
Properties
Molecular formula	C₆H₁₀O₃
Molar mass	130.14 g mol⁻¹
Exact mass	130.062994186 g mol^-1
Density	1.055 g cm^-3 (at 20 °C)
Melting point	8-10 °C, 281-283 K, 46-50 °F
Boiling point	85 °C, 358 K, 185 °F (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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

References

lysine→	Saccharopine · Allysine · α-Aminoadipic acid · α-Aminoadipate · 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

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

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

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Ornithine · Putrescine · Agmatine

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


phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid · Homogentisic acid · 4-Maleylacetoacetate

see urea cycle

Other


Cysteine metabolism	Cysteine sulfinic acid

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i