3-Hydroxyisobutyric acid (ECMDB00023) (M2MDB000005)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (3)
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
Description3-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
MOLSDFPDBSMILESInChI
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
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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:0.122PhysProp
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
Polarizability9.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
3-Hydroxyisobutyric acid + NAD <> 2-Aminomalonate semialdehyde + NADH
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9720000000-2a61310303ff8f2a7b42View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-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

Protein Details
1. 2-hydroxy-3-oxopropionate reductase
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.
Protein Details
2. NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG
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.
Protein Details
3. Uncharacterized oxidoreductase ygbJ
General function:
Not Available
Specific function:
Not Available
Gene Name:
ygbJ
Uniprot ID:
Q46888
Molecular weight:
Not Available