(3R)-3-Methyl-2-oxopentanoic acid
Basic information
- CAS
61748-89-8- Standard SMILES
CC[C@@H](C)C(=O)C(=O)O- InChIKey
JVQYSWDUAOAHFM-SCSAIBSYSA-N- Molecular formula
- C6H10O3
- Average molar mass
- 130.14 g/mol
- Monoisotopic mass
- 130.06299418
Overview
(R)-3-methyl-2-oxovaleric acid is the (R)-enantiomer of 3-methyl-2-oxovaleric acid. It is a conjugate acid of a (R)-3-methyl-2-oxovalerate. It is an enantiomer of a (S)-3-methyl-2-oxovaleric acid.
Names & identifiers
- Preferred name
- (3R)-3-Methyl-2-oxopentanoic acid
- IUPAC
- (3R)-3-methyl-2-oxopentanoic acid
Names & synonyms
(3R)-3-Methyl-2-oxopentanoic acid(R)-2-Oxo-3-methylpentanoic acidRefChem:1050244(R)-2-Oxo-3-methylpentanoate61748-89-8D-2-Keto-3-methylvalerate(R)-3-Methyl-2-oxopentanoic acidPentanoic acid, 3-methyl-2-oxo-, (R)-UNII-2N24YSA6YZ2N24YSA6YZ3-Methyl-2-oxo-pentanoic acid, (+)-Pentanoic acid, 3-methyl-2-oxo-, (3R)-
Show more names
2oxo-3R-methyl-pentanoic acid(3R)-2-oxoisoleucine(R)-OMVSCHEMBL3860250CHEBI:28379(r)-2-oxo-3-methylvaleric acid(R)-3-methyl-2-oxovaleric acid(+)-3-methyl-2-oxo-pentanoic acid
Database identifiers
- CAS
61748-89-8- PubChem CID
- 440877
- ChEBI
CHEBI:28379- UNII
- 2N24YSA6YZ
- Nikkaji
- J264.813J
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 128
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Branched fatty acids [FA0102]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Health EffectsChronically high levels of 3-methyl-2-oxovaleric acid are associated with Maple Syrup Urine Disease.
Toxicity Summary
3-Methyl-2-oxovaleric acid is produced from isoleucine by cytosolic branched chain aminotransferase 1, whereupon it is further degraded by branched chain keto acid dehydrogenase E1 to 2-methyl-1-hydroxybutyl-ThPP. It is used as a clinical marker for maple syrup urine disease (MSUD). MSUD is caused by a deficiency of the branched-chain -keto acid dehydrogenase complex resulting in an accumulation of branched-chain amino acids and the corresponding -keto-and -hydroxy acids in blood, urine and cerebrospinal fluid causing neurological damage and mental retardation.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
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Compound notes
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