Record Information
Version1.0
Creation date2011-09-21 00:07:10 UTC
Update date2015-10-09 22:30:25 UTC
Primary IDFDB022023
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hydroxy-3-methylbutyric acid
Description2-Hydroxy-3-methylbutyric acid is a metabolite found in the urine of patients with Phenylketonuria (PMID 7978272), Methylmalonic acidemia, Propionic acidemia, 3-Ketothiolase deficiency, Isovaleric acidemia, 3-Methylcrotonylglycemia, 3-Hydroxy-3-methylglutaric acidemia, Multiple carboxylase deficiency, Glutaric aciduria, Ornithine transcarbamylase deficiency, glyceroluria, Tyrosinemia type 1, Galactosemia, and Maple syrup urine disease (PMID 11048741) [HMDB]
CAS Number4026-18-0
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxyisopentanoic acidChEBI
2-Hydroxyisovaleric acidChEBI
3-Methyl-2-hydroxybutyric acidChEBI
alpha-Hydroxyisovaleric acidChEBI
2-HydroxyisopentanoateGenerator
2-Hydroxy-3-methylbutyrateGenerator
2-HydroxyisovalerateGenerator
3-Methyl-2-hydroxybutyrateGenerator
a-HydroxyisovalerateGenerator
a-Hydroxyisovaleric acidGenerator
alpha-HydroxyisovalerateGenerator
α-hydroxyisovalerateGenerator
α-hydroxyisovaleric acidGenerator
2-Hydroxy-3-methyl-butyric acidHMDB
2-Hydroxy-3-methylbutanoateHMDB
2-Hydroxy-3-methylbutanoic acidHMDB
2-OxyisovalerateHMDB
2-Oxyisovaleric acidHMDB
DL-2-Hydroxy-3-methylbutanoateHMDB
DL-2-Hydroxy-3-methylbutanoic acidHMDB
DL-2-HydroxyisovalerateHMDB
DL-2-Hydroxyisovaleric acidHMDB
DL-a-HydroxyisovalerateHMDB
DL-a-Hydroxyisovaleric acidHMDB
DL-alpha-HydroxyisovalerateHMDB
DL-alpha-Hydroxyisovaleric acidHMDB
2-Hydroxyisovaleric acid, monosodium salt, (S)-isomerMeSH
2-Hydroxyisovaleric acid, (S)-isomerMeSH
2-Hydroxyisovaleric acid, calcium (2:1) saltMeSH
2-Hydroxyisovaleric acid, (R)-isomerMeSH
2-hydroxy-3-methyl-Butyric acidhmdb
A-hydroxyisovaleratehmdb
A-hydroxyisovaleric acidhmdb
alpha-hydroxyisovaleratehmdb
alpha-hydroxyisovaleric acidhmdb
DL-a-hydroxyisovaleratehmdb
DL-a-hydroxyisovaleric acidhmdb
DL-alpha-hydroxyisovaleratehmdb
DL-alpha-hydroxyisovaleric acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility215 g/LALOGPS
logP0.1ALOGPS
logP0.42ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity27.84 m³·mol⁻¹ChemAxon
Polarizability11.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H10O3
IUPAC name2-hydroxy-3-methylbutanoic acid
InChI IdentifierInChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)
InChI KeyNGEWQZIDQIYUNV-UHFFFAOYSA-N
Isomeric SMILESCC(C)C(O)C(O)=O
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
Classification
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-3ceb85540106a01209a9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g1-9520000000-27e47b254facef447ecfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-01b9-9800000000-34c80f5b3cfe512db815View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-006t-9100000000-62b5dd0328186489f167View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kb-9400000000-4b607be60b20b11a9328View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-00di-9000000000-053084615922d2811fc0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-9000000000-c74232c34d7c991de0c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gi0-6900000000-9c5d211acf2118d6a136View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9100000000-fd55205401dd434cfdccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-44a71cd407c65a176f7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-6900000000-977b23edb76b18575dc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-9400000000-a265e0ef4d3a3366c0beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-a258a01f539f2e2cd1e7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID90190
ChEMBL IDCHEMBL1162479
KEGG Compound IDNot Available
Pubchem Compound ID99823
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00407
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference