You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB01571
Name2-Hydroxy-3-methylvalerate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-Hydroxy-3-methylpentanoic acid or 2-hydroxy-3-methylvaleric acid (HMVA) is an organic acid generated by L-isoleucine metabolism. It is derived from the reduction of 2-Keto-3-methylvaleric acid (KMVA), possibly through the action of a lactate dehydrogenase. There are 4 stereoisomers of HMVA (2S,3S-HMVA, 2R,3R-HMVA, 2S,3R-HMVA and 2R,3S-HMVA), of which the 2S,3S and 2S,3R derivatives are generally separable. [PMID: 1429566]
Structure
Thumb
Synonyms
  • (2R,3R)-2-Hydroxy-3-methyl-pentanoate
  • (2R,3R)-2-Hydroxy-3-methyl-pentanoic acid
  • (2R,3R)-2-Hydroxy-3-methylpentanoate
  • (2R,3R)-2-Hydroxy-3-methylpentanoic acid
  • 2-Hydroxy-3-methyl-pentanoate
  • 2-Hydroxy-3-methyl-valerate
  • 2-Hydroxy-3-methyl-valeric acid
  • 2-Hydroxy-3-methylpentanoate
  • 2-Hydroxy-3-methylvalerate
  • 2-Hydroxy-3-methylvaleric acid
  • a-Hydroxy-b-methylvalerate
  • a-Hydroxy-b-methylvaleric acid
  • alpha-Hydroxy-beta-methylvalerate
  • alpha-Hydroxy-beta-methylvaleric acid
  • HMVA
  • 2-Hydroxy-3-methyl-pentanoic acid
CAS number488-15-3
WeightAverage: 132.1577
Monoisotopic: 132.07864425
InChI KeyRILPIWOPNGRASR-RFZPGFLSSA-N
InChIInChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5-/m1/s1
IUPAC Name(2R,3R)-2-hydroxy-3-methylpentanoic acid
Traditional IUPAC Name2-hydroxy-3-methyl-valerate
Chemical FormulaC6H12O3
SMILESCC[C@@H](C)[C@@H](O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility149 g/LALOGPS
logP0.74ALOGPS
logP0.86ChemAxon
logS0.05ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability13.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1615 ± 81 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-ed210d81f7dd591ba305JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-070i-9430000000-6a69d25573a59e501509JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-6900000000-a4c1daf19028c3b5134fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-869a6d71fe88a292f540JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-b1a7373d307d666ee4d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-6900000000-f3e353eb7493baf38742JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q0-9500000000-7d4a297dfcfc8042262cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-befdfe1bd9ab81fcab68JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89228
HMDB IDHMDB00317
Pubchem Compound ID10796774
Kegg IDNot Available
ChemSpider ID8972081
FOODB IDFDB021944
Wikipedia IDNot Available
BioCyc IDNot Available