3-Hydroxyisobutyric acid (PAMDB000005)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000005
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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 104.1045
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Hydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct Parent Beta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
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:
3-Hydroxyisobutyric acid + NAD <> 2-Aminomalonate semialdehyde + NADH
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
• 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
Locus Tag:
PA4907
Molecular weight:
27.4 kDa
Reactions
3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.