Record Information
Version1.0
Creation date2011-09-21 00:04:23 UTC
Update date2020-09-17 15:40:45 UTC
Primary IDFDB021877
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. The severity of this disease varies from case to case (S)-3-hydroxyisobutyric acid can be converted into (S)-methylmalonic acid semialdehyde through its interaction with the enzymes 3-hydroxyisobutyrate dehydrogenase, mitochondrial and enoyl-CoA hydratase, mitochondrial. In humans, (S)-3-hydroxyisobutyric acid is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway (S)-3-Hydroxyisobutyric acid is an intermediate in the metabolic pathways of L-valine and L-thymine amino acids. The deficient enzyme in 3HiB-uria remains unclear (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 eosinophilic esophagitis, colorectal cancer, and diabetes mellitus type 2; (S)-3-hydroxyisobutyric acid has also been linked to the inborn metabolic disorder 3-hydroxyisobutyric aciduria.
CAS Number2068-83-9
Structure
Thumb
Synonyms
SynonymSource
(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
2-methyl-L-(+)-Hydracrylatehmdb
2-methyl-L-(+)-Hydracrylic acidhmdb
3-hydroxy-2-methyl-(S)-Propanoatehmdb
3-hydroxy-2-methyl-(S)-Propanoic acidhmdb
3-hydroxy-isobutyratehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H8O3
IUPAC name(2S)-3-hydroxy-2-methylpropanoic acid
InChI IdentifierInChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyDBXBTMSZEOQQDU-VKHMYHEASA-N
Isomeric SMILESC[C@@H](CO)C(O)=O
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
Classification
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

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-3-Hydroxyisobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9000000000-dd1c22f7a337d3289497Spectrum
Predicted GC-MS(S)-3-Hydroxyisobutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gr-9720000000-2a61310303ff8f2a7b42Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-8900000000-b51c12e744025b833f31Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9100000000-0d72fcffff267d7bc980Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfs-9400000000-b3b27a9cc8fd4ebe9eb1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-9500000000-543c65dad21c233fc8a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-9000000000-7b7dcb34e28cb55ddafbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-27deee4c6a386a43ebc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-a7aa709e1985355b4bd9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi0-9200000000-01a40fbe4d19283ef080Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-622de763b5ea31ff4ee6Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID389707
ChEMBL IDNot Available
KEGG Compound IDC06001
Pubchem Compound ID440873
Pubchem Substance IDNot Available
ChEBI ID18064
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00023
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID37034
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-hydroxyisobutyryl-CoA hydrolase, mitochondrialHIBCHQ6NVY1
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference