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CHEBI:59783 - 2-hydroxy-4-methylvaleric acid

ChEBI IDCHEBI:59783
ChEBI Name2-hydroxy-4-methylvaleric acid
Stars
DefinitionA valeric acid derivative having a hydroxy substituent at the 2-position and a methyl substituent at the 4-position; an α-hydroxy analogue of leucine. A bacterial metabolite, it has also been isolated from amniotic fluid, was found in a patient with dihydrolipoyl dehydrogenase deficiency and is present in the urine of patients with short bowel syndrome.
Last Modified11 October 2016
Submitterzjosephs
DownloadsMolfile
FormulaC6H12O3
Net Charge0
Average Mass132.159
Monoisotopic Mass132.07864
SMILESCC(C)CC(O)C(=O)O
InChIInChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)
InChIKeyLVRFTAZAXQPQHI-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
2-hydroxy-4-methylvaleric acid (CHEBI:59783) has functional parent valeric acid (CHEBI:17418)
2-hydroxy-4-methylvaleric acid (CHEBI:59783) has role metabolite (CHEBI:25212)
2-hydroxy-4-methylvaleric acid (CHEBI:59783) is a 2-hydroxy fatty acid (CHEBI:10283)
2-hydroxy-4-methylvaleric acid (CHEBI:59783) is a branched-chain fatty acid (CHEBI:35819)
2-hydroxy-4-methylvaleric acid (CHEBI:59783) is conjugate acid of 2-hydroxy-4-methylvalerate (CHEBI:133577)
Incoming Relation(s)
(R)-2-hydroxy-4-methylpentanoic acid (CHEBI:55534) is a 2-hydroxy-4-methylvaleric acid (CHEBI:59783)
(S)-2-hydroxy-4-methylpentanoic acid (CHEBI:44510) is a 2-hydroxy-4-methylvaleric acid (CHEBI:59783)
2-hydroxy-4-methylvalerate (CHEBI:133577) is conjugate base of 2-hydroxy-4-methylvaleric acid (CHEBI:59783)
IUPAC Name 
2-hydroxy-4-methylpentanoic acid
Synonyms  Source
alpha-Hydroxyisocaproic acidChEBI
Leucic acidChemIDplus
2-hydroxyisocaproic acidChEBI
2-hydroxyisohexanoic acidChEBI
leucinic acidChEBI
Manual XrefsDatabases
HMDB0000665HMDB
LMFA01050381LIPID MAPS
Registry NumbersSources
Reaxys:1721733Reaxys
CAS:498-36-2ChemIDplus
Citations