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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-10 15:02:48 UTC
HMDB IDHMDB0000336
Secondary Accession Numbers
  • HMDB00336
Metabolite Identification
Common Name(R)-3-Hydroxyisobutyric acid
Description(R)-3-Hydroxyisobutyric acid (3-HIBA) is an organic acid. The chiral metabolites 3-hydroxyisobutyric acid (HIBA) and 3-aminoisobutyric acid (AIBA) are intermediates in the pathways of L-valine and thymine and play an important role in the diagnosis of the very rare inherited metabolic diseases 3-hydroxyisobutyric aciduria (OMIM: 236795 ) and methylmalonic semialdehyde dehydrogenase deficiency (OMIM: 603178 ) (PMID: 10686279 ).
Structure
Data?1562770968
Synonyms
ValueSource
(R)-3-HydroxyisobutyrateGenerator
(R)-3-Hydroxy-2-methylpropionateHMDB
(R)-3-Hydroxy-2-methylpropionic acidHMDB
2-Methyl-(R)-hydracrylateHMDB
2-Methyl-(R)-hydracrylic acidHMDB
3-Hydroxy-2-methylpropionateHMDB
D-(-)-3-HydroxyisobutyrateHMDB
D-(-)-3-Hydroxyisobutyric acidHMDB
D-b-HydroxyisobutyrateHMDB
D-b-Hydroxyisobutyric acidHMDB
delta-(-)-3-HydroxyisobutyrateHMDB
delta-(-)-3-Hydroxyisobutyric acidHMDB
delta-beta-HydroxyisobutyrateHMDB
delta-beta-Hydroxyisobutyric acidHMDB
R-b-HydroxyisobutyrateHMDB
R-b-Hydroxyisobutyric acidHMDB
R-beta-HydroxyisobutyrateHMDB
R-beta-Hydroxyisobutyric acidHMDB
3R-Hydroxy-isobutyrateHMDB
(2R)-3-Hydroxy-2-methylpropanoic acidHMDB
(2R)-3-Hydroxy-2-methylpropionic acidHMDB
(R)-3-Hydroxy-2-methyl-propanoic acidHMDB
(R)-3-Hydroxy-2-methyl-propionic acidHMDB
(R)-3-Hydroxy-2-methylpropanoic acidHMDB
(R)-3-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-methylpropanoic acidHMDB
3-Hydroxy-2-methylpropionic acidHMDB
3-Hydroxyisobutyric acidHMDB
D-beta-Hydroxyisobutyric acidHMDB
D-β-Hydroxyisobutyric acidHMDB
DL-3-Hydroxyisobutyric acidHMDB
R-3-Hydroxyisobutyric acidHMDB
R-β-Hydroxyisobutyric acidHMDB
beta-Hydroxyisobutyric acidHMDB
β-Hydroxyisobutyric acidHMDB
3-Hydroxy-2-isobutyrateHMDB
3-Hydroxy-2-isobutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name(2R)-3-hydroxy-2-methylpropanoic acid
Traditional Name(R)-3-hydroxyisobutyric acid
CAS Registry Number1910-47-0
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-/m1/s1
InChI KeyDBXBTMSZEOQQDU-GSVOUGTGSA-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
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-00f48b549b40517fc756JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gr-9720000000-2a61310303ff8f2a7b42JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9500000000-543c65dad21c233fc8a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-9000000000-7b7dcb34e28cb55ddafbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-27deee4c6a386a43ebc3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-a7aa709e1985355b4bd9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-9200000000-01a40fbe4d19283ef080JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-622de763b5ea31ff4ee6JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified21.0 +/- 2.0 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified6 +/- 3 uMAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified<95 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified38.0 +/- 5.0 uMAdult (>18 years old)Both
Diabetes
details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Avogaro A, Bier DM: Contribution of 3-hydroxyisobutyrate to the measurement of 3-hydroxybutyrate in human plasma: comparison of enzymatic and gas-liquid chromatography-mass spectrometry assays in normal and in diabetic subjects. J Lipid Res. 1989 Nov;30(11):1811-7. [PubMed:2614280 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021960
KNApSAcK IDNot Available
Chemspider ID9392288
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11217234
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceSprecher, M.; Sprinson, David B. Preparation of (R)-b-hydroxyisobutyric acid from threo-3-methyl-L-aspartate. Journal of Biological Chemistry (1966), 241(4), 868-71.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. [PubMed:10686279 ]
  2. Gray RG, Pollitt RJ, Webley J: Methylmalonic semialdehyde dehydrogenase deficiency: demonstration of defective valine and beta-alanine metabolism and reduced malonic semialdehyde dehydrogenase activity in cultured fibroblasts. Biochem Med Metab Biol. 1987 Aug;38(1):121-4. [PubMed:3117077 ]
  3. Roe CR, Struys E, Kok RM, Roe DS, Harris RA, Jakobs C: Methylmalonic semialdehyde dehydrogenase deficiency: psychomotor delay and methylmalonic aciduria without metabolic decompensation. Mol Genet Metab. 1998 Sep;65(1):35-43. [PubMed:9787093 ]