''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
CAS Number	816-66-0^Y
3D model (JSmol)	Interactive image Interactive image
3DMet	B00066
Beilstein Reference	1701823
ChEBI	CHEBI:48430^Y
ChemSpider	69^Y
DrugBank	DB03229^Y
ECHA InfoCard	100.011.304
EC Number	212-435-5
IUPHAR/BPS	4656
KEGG	C00233^Y
MeSH	Alpha-ketoisocaproic+acid
PubChem CID	70
UN number	3265
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
SMILES CC(C)CC(=O)C(O)=O O=C(C(=O)O)CC(C)C
Properties
Chemical formula	C₆H₁₀O₃
Molar mass	130.14 g·mol⁻¹
Density	1.055 g cm⁻³ (at 20 °C)
Melting point	8 to 10 °C (46 to 50 °F; 281 to 283 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EU classification (DSD) (outdated)	C
R-phrases (outdated)	R34
S-phrases (outdated)	S26, S36/37/39, S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

α-Ketoisocaproic acid is an intermediate in the metabolism of leucine.^[2]

Leucine metabolism

Human metabolic pathway for HMB and isovaleryl-CoA, relative to leucine.^[2] Of the two major pathways, leucine is mostly metabolized into isovaleryl-CoA, while only 5% or so is metabolized into HMB.^[2]

References

↑ http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=70
1 2 3 Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). "International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)". J. Int. Soc. Sports. Nutr. 10 (1): 6. PMC 3568064 . PMID 23374455. doi:10.1186/1550-2783-10-6.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	α-Ketoisocaproic acid β-hydroxy β-methylbutyric acid β-hydroxy β-methylbutyryl-CoA 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 Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

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

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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