(S)-3-Hydroxyisobutyric acid (YMDB00337)

Identification
YMDB IDYMDB00337
Name(S)-3-Hydroxyisobutyric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(S)-3-Hydroxyisobutyric acid, also known as (S)-3-hydroxy-2-methylpropanoate or 3-hydroxy-isobutyrate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom (S)-3-Hydroxyisobutyric acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-3-Hydroxyisobutyric acid exists in all living species, ranging from bacteria to humans (S)-3-Hydroxyisobutyric acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (S)-3-Hydroxyisobutyric acid
  • 2-methyl-L-(+)-Hydracrylate
  • 2-methyl-L-(+)-Hydracrylic acid
  • 3-hydroxy-2-methyl-(S)-Propanoate
  • 3-hydroxy-2-methyl-(S)-Propanoic acid
  • 3-Hydroxy-2-methylpropanoate
  • 3-Hydroxy-2-methylpropanoic acid
  • 3-hydroxy-isobutyrate
  • 3-Hydroxyisobutyrate
  • 3-Hydroxyisobutyric acid
  • (S)-3-Hydroxy-2-methylpropanoic acid
  • (S)-3-Hydroxy-2-methylpropionic acid
  • (S)-3-Hydroxy-2-methylpropanoate
  • (S)-3-Hydroxy-2-methylpropionate
  • (S)-3-Hydroxyisobutyrate
  • 3-Hydroxy(iso)butyric acid
  • (2S)-3-Hydroxy-2-methylpropanoic acid
  • (2S)-3-Hydroxy-2-methylpropionic acid
  • (S)-beta-Hydroxyisobutyric acid
  • (S)-Β-hydroxyisobutyric acid
  • (±)-3-hydroxy-2-methylpropanoic acid
  • (±)-3-hydroxy-2-methylpropionic acid
  • 2-(Hydroxymethyl)propanoic acid
  • 2-(Hydroxymethyl)propionic acid
  • 2-Methyl-3-hydroxypropanoic acid
  • 2-Methyl-3-hydroxypropionic acid
  • 3-HIBA
  • 3-Hydroxy-2-methylpropionic acid
  • DL-3-Hydroxyisobutyric acid
  • L-(+)-beta-Hydroxyisobutyric acid
  • L-(+)-Β-hydroxyisobutyric acid
  • beta-Hydroxyisobutyric acid
  • Β-hydroxyisobutyric acid
  • 3-Hydroxy-2-isobutyrate
  • 3-Hydroxy-2-isobutyric acid
CAS number2068-83-9
WeightAverage: 104.1045
Monoisotopic: 104.047344122
InChI KeyDBXBTMSZEOQQDU-VKHMYHEASA-N
InChIInChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
IUPAC Name(2S)-3-hydroxy-2-methylpropanoic acid
Traditional IUPAC Name(S)-3-hydroxyisobutyric acid
Chemical FormulaC4H8O3
SMILES[H]OC(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 Solubility571 g/LALOGPS
logP-0.47ALOGPS
logP-0.26ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.62 m³·mol⁻¹ChemAxon
Polarizability9.98 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 ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9000000000-dd1c22f7a337d3289497JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9720000000-2a61310303ff8f2a7b42JSpectraViewer
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)splash10-0zfr-8900000000-b51c12e744025b833f31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9100000000-0d72fcffff267d7bc980JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9500000000-543c65dad21c233fc8a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-9000000000-7b7dcb34e28cb55ddafbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-27deee4c6a386a43ebc3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-a7aa709e1985355b4bd9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-9200000000-01a40fbe4d19283ef080JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-622de763b5ea31ff4ee6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ap3-9000000000-6c76b805d02ad21ab06aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aou-9000000000-fc5e7dbe1e224cc87d4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-021ab3207a43699617f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uki-9700000000-04713faa703ce789efb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9100000000-b0202d15bd6411bc7d80JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-d2c32880fd340aac0badJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Robison, Robert S.; Doremus, Michael G.L-(+)-b-Hydroxyisobutyric acid by fermentation. U.S. (1986), 5 pp.
External Links:
ResourceLink
CHEBI ID37373
HMDB IDHMDB00023
Pubchem Compound ID87
Kegg IDC01188
ChemSpider ID389707
FOODB IDFDB021877
Wikipedia3-Hydroxyisobutyric_acid
BioCyc ID3-HYDROXY-ISOBUTYRATE

Enzymes

Protein Details
1. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA. Has an indirect role in endocytic membrane trafficking. May have a function in protein biosynthesis in mitochondrial small ribosomal subunit
Gene Name:
EHD3
Uniprot ID:
P28817
Molecular weight:
56287.89844
Reactions
3-hydroxy-2-methylpropanoyl-CoA + H(2)O → CoA + 3-hydroxy-2-methylpropanoate.