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2-Hydroxy-3-methylbutyric acid (YMDB01318)

Identification
YMDB IDYMDB01318
Name2-Hydroxy-3-methylbutyric acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-Hydroxy-3-methylbutyric acid, also known as a-hydroxyisovalerate or 2-hydroxyisopentanoic acid, 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
  • 2-hydroxy-3-methyl-Butyric acid
  • 2-Hydroxy-3-methylbutanoate
  • 2-Hydroxy-3-methylbutanoic acid
  • 2-Hydroxy-3-methylbutyrate
  • 2-Hydroxyisopentanoate
  • 2-Hydroxyisopentanoic acid
  • 2-Hydroxyisovalerate
  • 2-Hydroxyisovaleric acid
  • 2-Oxyisovalerate
  • 2-Oxyisovaleric acid
  • 3-Methyl-2-hydroxybutyrate
  • 3-Methyl-2-hydroxybutyric acid
  • A-hydroxyisovalerate
  • A-hydroxyisovaleric acid
  • alpha-hydroxyisovalerate
  • alpha-hydroxyisovaleric acid
  • DL-2-Hydroxy-3-methylbutanoate
  • DL-2-Hydroxy-3-methylbutanoic acid
  • DL-2-Hydroxyisovalerate
  • DL-2-Hydroxyisovaleric acid
  • DL-a-hydroxyisovalerate
  • DL-a-hydroxyisovaleric acid
  • DL-alpha-hydroxyisovalerate
  • DL-alpha-hydroxyisovaleric acid
  • Α-hydroxyisovalerate
  • Α-hydroxyisovaleric acid
  • 2-Hydroxyisovaleric acid, monosodium salt, (S)-isomer
  • 2-Hydroxyisovaleric acid, (S)-isomer
  • 2-Hydroxyisovaleric acid, calcium (2:1) salt
  • 2-Hydroxyisovaleric acid, (R)-isomer
CAS number4026-18-0
WeightAverage: 118.1311
Monoisotopic: 118.062994186
InChI KeyNGEWQZIDQIYUNV-UHFFFAOYSA-N
InChIInChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)
IUPAC Name2-hydroxy-3-methylbutanoic acid
Traditional IUPAC Name2-hydroxyisovaleric acid
Chemical FormulaC5H10O3
SMILES[H]OC(=O)C([H])(O[H])C([H])(C([H])([H])[H])C([H])([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility215 g/LALOGPS
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
Polarizability11.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-3ceb85540106a01209a9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g1-9520000000-27e47b254facef447ecfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-01b9-9800000000-34c80f5b3cfe512db815JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-006t-9100000000-62b5dd0328186489f167JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kb-9400000000-4b607be60b20b11a9328JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00di-9000000000-053084615922d2811fc0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-9000000000-c74232c34d7c991de0c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-052f-9000000000-1837dbe9ec7e7648abacJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0gbc-9400000000-3dae3f739ba9de64475aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-6900000000-9c5d211acf2118d6a136JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9100000000-fd55205401dd434cfdccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-44a71cd407c65a176f7dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-6900000000-977b23edb76b18575dc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-9400000000-a265e0ef4d3a3366c0beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-a258a01f539f2e2cd1e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-9100000000-4440e0dd7c3edf6166aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-848921fdd36001ccc2adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ec34045be03977dd8e79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-d5f27e5fc2f84d237f6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-7900000000-d8e0dd0fbaecb6b1909eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a096d70c21dd426764cbJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Dickinson, J. R., Harrison, S. J., Hewlins, M. J. (1998). "An investigation of the metabolism of valine to isobutyl alcohol in Saccharomyces cerevisiae." J Biol Chem 273:25751-25756.9748245
Synthesis Reference:Perekalin, 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.
External Links:
ResourceLink
CHEBI ID60645
HMDB IDHMDB00407
Pubchem Compound ID99823
Kegg IDNot Available
ChemSpider ID90190
FOODB IDFDB022023
Wikipedia IDNot Available
BioCyc IDNot Available