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Record Information
Version1.0
Creation Date2016-09-30 22:18:36 UTC
Update Date2020-03-18 18:12:11 UTC
BMDB IDBMDB0000023
Secondary Accession Numbers
  • BMDB00023
Metabolite Identification
Common Name(S)-3-Hydroxyisobutyric acid
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 (S)-3-Hydroxyisobutyric acid, with regard to humans, has been found to be associated with several diseases such as diabetes mellitus type 2, eosinophilic esophagitis, and colorectal cancer; (S)-3-hydroxyisobutyric acid has also been linked to the inborn metabolic disorder 3-hydroxyisobutyric aciduria.
Structure
Thumb
Synonyms
ValueSource
(S)-3-Hydroxy-2-methylpropanoic acidChEBI
(S)-3-Hydroxy-2-methylpropionic acidChEBI
(S)-3-Hydroxy-2-methylpropanoateGenerator
(S)-3-Hydroxy-2-methylpropionateGenerator
(S)-3-HydroxyisobutyrateGenerator
2-Methyl-L-(+)-hydracrylateHMDB
2-Methyl-L-(+)-hydracrylic acidHMDB
3-Hydroxy(iso)butyric acidHMDB
3-Hydroxy-2-methyl-(S)-propanoateHMDB
3-Hydroxy-2-methyl-(S)-propanoic acidHMDB
3-Hydroxy-2-methylpropanoateHMDB
3-Hydroxy-2-methylpropanoic acidHMDB
3-Hydroxy-isobutyrateHMDB
3-HydroxyisobutyrateHMDB
3-Hydroxyisobutyric acidHMDB
(2S)-3-Hydroxy-2-methylpropanoic acidHMDB
(2S)-3-Hydroxy-2-methylpropionic acidHMDB
(S)-beta-Hydroxyisobutyric acidHMDB
(S)-Β-hydroxyisobutyric acidHMDB
(±)-3-hydroxy-2-methylpropanoic acidHMDB
(±)-3-hydroxy-2-methylpropionic acidHMDB
2-(Hydroxymethyl)propanoic acidHMDB
2-(Hydroxymethyl)propionic acidHMDB
2-Methyl-3-hydroxypropanoic acidHMDB
2-Methyl-3-hydroxypropionic acidHMDB
3-HIBAHMDB
3-Hydroxy-2-methylpropionic acidHMDB
DL-3-Hydroxyisobutyric acidHMDB
L-(+)-beta-Hydroxyisobutyric acidHMDB
L-(+)-Β-hydroxyisobutyric acidHMDB
beta-Hydroxyisobutyric acidHMDB
Β-hydroxyisobutyric acidHMDB
3-Hydroxy-2-isobutyrateHMDB
3-Hydroxy-2-isobutyric acidHMDB
(S)-3-Hydroxyisobutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name(2S)-3-hydroxy-2-methylpropanoic acid
Traditional Name(S)-3-hydroxyisobutyric acid
CAS Registry Number2068-83-9
SMILES
C[C@@H](CO)C(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyDBXBTMSZEOQQDU-VKHMYHEASA-N
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
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9000000000-dd1c22f7a337d3289497View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9720000000-2a61310303ff8f2a7b42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-8900000000-b51c12e744025b833f31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9100000000-0d72fcffff267d7bc980View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9500000000-543c65dad21c233fc8a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-9000000000-7b7dcb34e28cb55ddafbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-27deee4c6a386a43ebc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-a7aa709e1985355b4bd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-9200000000-01a40fbe4d19283ef080View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-622de763b5ea31ff4ee6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine, and Isoleucine DegradationSMP0087234Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021877
KNApSAcK IDNot Available
Chemspider ID389707
KEGG Compound IDC06001
BioCyc IDNot Available
BiGG ID37034
Wikipedia LinkNot Available
METLIN ID483
PubChem Compound440873
PDB IDNot Available
ChEBI ID37373
References
Synthesis ReferenceRobison, Robert S.; Doremus, Michael G.L-(+)-b-Hydroxyisobutyric acid by fermentation. U.S. (1986), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
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 (By similarity).
Gene Name:
HIBCH
Uniprot ID:
Q2HJ73
Molecular weight:
43349.0
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
HIBADH
Uniprot ID:
Q2HJD7
Molecular weight:
35410.0