Record Information
Version2.0
Creation Date2012-05-31 09:55:24 -0600
Update Date2015-09-13 12:56:05 -0600
Secondary Accession Numbers
  • ECMDB00023
Identification
Name:3-Hydroxyisobutyric acid
Description:3-Hydroxyisobutyric acid is a member of the chemical class known as Beta Hydroxy Acids and Derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-Hydroxyisobutyric acid (or 3-hydroxy-2-methylpropanoic acid) is an intermediate in the metabolism of valine. (WikiPedia)
Structure
Thumb
Synonyms:
  • (S)-3-Hydroxyisobutyrate
  • (S)-3-Hydroxyisobutyric acid
  • (S)-b-Hydroxyisobutyrate
  • (S)-b-Hydroxyisobutyric acid
  • 2-Methyl-L-(+)-Hydracrylate
  • 2-Methyl-L-(+)-Hydracrylic acid
  • 3-Hydroxy(iso)butyrate
  • 3-hydroxy(iso)butyric 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-Hydroxy-isobutyric acid
  • 3-Hydroxyisobutyrate
  • 3-Hydroxyisobutyric acid
  • 3-OH-iso-but
  • 3-OH-isobutyrate
  • 3-OH-Isobutyric acid
  • L-(+)-b-Hydroxyisobutyrate
  • L-(+)-b-Hydroxyisobutyric acid
  • L-(+)-beta-Hydroxyisobutyrate
  • L-(+)-beta-Hydroxyisobutyric acid
  • L-(+)-β-Hydroxyisobutyrate
  • L-(+)-β-Hydroxyisobutyric acid
Chemical Formula:C4H8O3
Weight:Average: 104.1045
Monoisotopic: 104.047344122
InChI Key:DBXBTMSZEOQQDU-UHFFFAOYSA-N
InChI:InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
CAS number:2068-83-9
IUPAC Name:3-hydroxy-2-methylpropanoic acid
Traditional IUPAC Name:3-hydroxyisobutyric acid
SMILES:CC(CO)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy 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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:0.122PhysProp
Predicted Properties
PropertyValueSource
Water Solubility571.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.62 m3·mol-1ChemAxon
Polarizability9.99 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00gr-9720000000-2a61310303ff8f2a7b42View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0a4i-9000000000-00f48b549b40517fc756View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9300000000-4c7d7d3eb2cd6dd4aff2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-9000000000-e1dfa9560197f964f43bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-544a47ca2aad2922036bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-4900000000-d99c3860d33949056e8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi9-9200000000-1d2f57daecf1f2dc2f08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e6639c28f3299b1ba44eView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18064
HMDB IDHMDB00023
Pubchem Compound ID87
Kegg IDC01188
ChemSpider ID85
Wikipedia ID3-Hydroxyisobutyric acid
BioCyc ID3-HYDROXY-ISOBUTYRATE
EcoCyc ID3-HYDROXY-ISOBUTYRATE

Enzymes

General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
(R)-glycerate + NAD(P)(+) = 2-hydroxy-3- oxopropanoate + NAD(P)H
Gene Name:
garR
Uniprot ID:
P0ABQ2
Molecular weight:
30427
Reactions
D-glycerate + NAD(P)(+) = 2-hydroxy-3-oxopropanoate + NAD(P)H.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADP-dependent oxidation of L-allo- threonine to L-2-amino-3-keto-butyrate, which is spontaneously decarboxylated into aminoacetone. Also acts on L-serine, D-serine, D-threonine, D-3-hydroxyisobutyrate, L-3-hydroxyisobutyrate, D- glycerate and L-glycerate
Gene Name:
ydfG
Uniprot ID:
P39831
Molecular weight:
27249
Reactions
3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.
General function:
Not Available
Specific function:
Not Available
Gene Name:
ygbJ
Uniprot ID:
Q46888
Molecular weight:
Not Available