β-Ketoisocaproic acid - Misplaced Pages

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β-Ketoisocaproic acid
Names

Preferred IUPAC name 4-Methyl-3-oxopentanoic acid
Other names 4-Methyl-3-oxopentanoic acid 4-Methyl-3-oxovaleric acid Isobutanoylacetic acid Isobutyrylacetic acid
Identifiers
CAS Number	5650-76-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29024
ChemSpider	389038
KEGG	C03467
MeSH	Beta-ketoisocaproic+acid
PubChem CID	440024
UNII	FWW4Q5U8HP
CompTox Dashboard (EPA)	DTXSID60331463
InChI Key: ZXLSKTZECNUVIS-UHFFFAOYSA-N
SMILES CC(C)C(CC(O)=O)=O
Properties
Chemical formula	C₆H₁₀O₃
Molar mass	130.143 g·mol
Density	1.1 g cm (at 20 °C)
Boiling point	236 °C (457 °F; 509 K) ±23 at 760 mmHg
log P	0.36
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

β-Ketoisocaproic acid, also known as 4-methyl-3-oxopentanoic acid, is an intermediate in the metabolism of leucine. Its metabolic precursor and metabolic product in the leucine metabolic pathway are β-leucine and β-ketoisocaproyl-CoA, respectively.

References

^ Kohlmeier M (May 2015). "Leucine". Nutrient Metabolism: Structures, Functions, and Genes (2nd ed.). Academic Press. pp. 385–388, Figure 8.57. ISBN 978-0-12-387784-0. Retrieved 6 June 2016. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds ...
"Leucine metabolism". BRENDA. Technische Universität Braunschweig. Archived from the original on 17 August 2016. Retrieved 12 August 2016.

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-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

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

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 α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA

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

Other

Cysteine metabolism	Cysteine sulfinic acid

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