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CHEBI:55536 - (2R,3S)-2-hydroxy-3-methylpentanoic acid

ChEBI IDCHEBI:55536
ChEBI Name(2R,3S)-2-hydroxy-3-methylpentanoic acid
Stars
ASCII Name(2R,3S)-2-hydroxy-3-methylpentanoic acid
DefinitionA valeric acid derivative having an (R)-hydroxy substituent at the 2-position and an (S)-methyl substituent at the 3-position; one of 4 steroisomers of 2-hydroxy-3-methylpentanoic acid, generated by isoleucine metabolism. Found at significantly higher levels than normal in patients with maple syrup urine disease (MSUD).
Last Modified19 August 2016
SubmitterSteve
DownloadsMolfile
FormulaC6H12O3
Net Charge0
Average Mass132.159
Monoisotopic Mass132.07864
SMILESCC[C@H](C)[C@@H](O)C(=O)O
InChIInChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5+/m0/s1
InChIKeyRILPIWOPNGRASR-CRCLSJGQSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
ChEBI Ontology
Outgoing Relation(s)
(2R,3S)-2-hydroxy-3-methylpentanoic acid (CHEBI:55536) has functional parent valeric acid (CHEBI:17418)
(2R,3S)-2-hydroxy-3-methylpentanoic acid (CHEBI:55536) is a (2R)-2-hydroxy monocarboxylic acid (CHEBI:17893)
(2R,3S)-2-hydroxy-3-methylpentanoic acid (CHEBI:55536) is a 2-hydroxy-3-methylpentanoic acid (CHEBI:133083)
(2R,3S)-2-hydroxy-3-methylpentanoic acid (CHEBI:55536) is conjugate acid of (2R,3S)-2-hydroxy-3-methylpentanoate (CHEBI:55537)
Incoming Relation(s)
(2R,3S)-2-hydroxy-3-methylpentanoate (CHEBI:55537) is conjugate base of (2R,3S)-2-hydroxy-3-methylpentanoic acid (CHEBI:55536)
IUPAC Name 
(2R,3S)-2-hydroxy-3-methylpentanoic acid
Synonyms  Source
(2R,3S)-2-hydroxy-3-methylvaleric acidChEBI
(2R,3S)-HMVAChEBI
HMVAChEBI
(2R,3S)-isoleucic acidChEBI
(R,S)-isoleucic acidChEBI
Registry NumbersSources
Beilstein:1721800Beilstein
Citations