Showing metabocard for 2-Hydroxy-3-methylbutyric acid (BMDB0000407)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:11 UTC
Update Date2020-05-11 20:36:57 UTC
BMDB IDBMDB0000407
Secondary Accession Numbers
  • BMDB00407
Metabolite Identification
Common Name2-Hydroxy-3-methylbutyric acid
Description2-Hydroxy-3-methylbutyric acid, also known as a-hydroxyisovaleric acid or 2-oxyisovalerate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Hydroxy-3-methylbutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-(+)-2-Hydroxy-3-methylbutanoic acidChEBI
(S)-(+)-2-Hydroxy-3-methylbutyric acidChEBI
2-Hydroxy-3-methyl-(S)-(+)-butyric acidChEBI
2-HydroxyisovalerateChEBI
2-OxyisovalerateChEBI
a-Hydroxyisovaleric acidChEBI
L-(+)-2-Hydroxyisovaleric acidChEBI
L-(+)-alpha-Hydroxyisovaleric acidChEBI
(S)-(+)-2-Hydroxy-3-methylbutanoateGenerator
(S)-(+)-2-Hydroxy-3-methylbutyrateGenerator
2-Hydroxy-3-methyl-(S)-(+)-butyrateGenerator
2-Hydroxyisovaleric acidGenerator
2-Oxyisovaleric acidGenerator
a-HydroxyisovalerateGenerator
L-(+)-2-HydroxyisovalerateGenerator
L-(+)-a-HydroxyisovalerateGenerator
L-(+)-a-Hydroxyisovaleric acidGenerator
L-(+)-alpha-HydroxyisovalerateGenerator
L-(+)-Α-hydroxyisovalerateGenerator
L-(+)-Α-hydroxyisovaleric acidGenerator
2-Hydroxy-3-methylbutyrateGenerator
(S)-2-Hydroxy-3-methylbutyrateGenerator
Chemical FormulaC5H10O3
Average Molecular Weight118.132
Monoisotopic Molecular Weight118.062994182
IUPAC Name(2S)-2-hydroxy-3-methylbutanoic acid
Traditional Nameα-hydroxyisovaleric acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(C(C)C)C(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m0/s1
InChI KeyNGEWQZIDQIYUNV-BYPYZUCNSA-N
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
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.1ALOGPS
logP0.42ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity27.84 m³·mol⁻¹ChemAxon
Polarizability11.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-fc8b9a9c04a409f04e31View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g1-9520000000-27e47b254facef447ecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-5900000000-a345580097c57d4f897eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9100000000-44cb49d34a5cbb964630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-cf891efb4728ce585c3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-7900000000-d02483bb5540a69aab06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9300000000-af738058e51afe59ff5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-72ab759fca5a6a08f3e8View in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0062584
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound853180
PDB IDNot Available
ChEBI ID60631
References
Synthesis ReferencePerekalin, V. V.; Petryaeva, A. K.; Zobacheva, M. M.; Metelkina, E. L. A new method of synthesis of a-hydroxy and a-oxo acids. Doklady Akademii Nauk SSSR (1966), 166(5), 1129-31.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available