Showing metabocard for 2-Methyl-3-hydroxybutyric acid (BMDB0000354)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:10 UTC
Update Date2020-04-22 15:03:07 UTC
BMDB IDBMDB0000354
Secondary Accession Numbers
  • BMDB00354
Metabolite Identification
Common Name2-Methyl-3-hydroxybutyric acid
Description2-Methyl-3-hydroxybutyric acid, also known as 3-hydroxy-2-methylbutyric acid or 2-methyl-3-hydroxybutanoate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Methyl-3-hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methyl-3-hydroxybutyric acid is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Methyl-3-hydroxybutanoic acidChEBI
3-Hydroxy-2-methylbutyric acidChEBI
2-Methyl-3-hydroxybutanoateGenerator
3-Hydroxy-2-methylbutyrateGenerator
2-Methyl-3-hydroxybutyrateGenerator
3-Hydroxy-2-methyl-butyrateHMDB
3-Hydroxy-2-methyl-butyric acidHMDB
3-Hydroxy-2-methylbutanoateHMDB
3-Hydroxy-2-methylbutanoic acidHMDB
a-Methyl-b-hydroxybutyrateHMDB
a-Methyl-b-hydroxybutyric acidHMDB
alpha-Methyl-beta-hydroxybutyrateHMDB
alpha-Methyl-beta-hydroxybutyric acidHMDB
NilateHMDB
Nilic acidHMDB
2-Methyl-3-hydroxybutyric acid, (R-(r*,s*))-isomerHMDB
Chemical FormulaC5H10O3
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
IUPAC Name3-hydroxy-2-methylbutanoic acid
Traditional Namenilic acid
CAS Registry Number473-86-9
SMILES
CC(O)C(C)C(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)
InChI KeyVEXDRERIMPLZLU-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.13ALOGPS
logP0.16ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.04 m³·mol⁻¹ChemAxon
Polarizability11.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0097-9100000000-4296c67313a78a015074View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9610000000-ea139d8674dafe6ab92aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-0900000000-c32a93ee8130e6925701View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-3900000000-43c640882c221c34cff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-9500000000-f67232e28fb95b61d1f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-da7c5873617fe20d6385View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-5900000000-bab83930d1557839e6f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9100000000-50701029b9e5b3af2fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-dd1dac699c164a7b71f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-8900000000-6e362f577b3d827a8387View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9100000000-6950ab2628a11bf6839aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-5278bf25a974c9f30369View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-9400000000-aee3a280a6df1ae985b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-45e4e2c8c6ea7216859fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9000000000-845222220a578798d8ceView in MoNA
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Blood
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis		 details
HMDB IDHMDB0000354
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021977
KNApSAcK IDNot Available
Chemspider ID141015
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3786
PubChem Compound160471
PDB IDNot Available
ChEBI ID37051
References
Synthesis ReferenceInoue, Yoshio; Sano, Fumitaka; Nakamura, Kazuhiro; Yoshie, Naoko; Saito, Yuji; Satoh, Hiroyasu; Mino, Takashi; Matsuo, Tomonori; Doi, Yoshiharu. Microstructure of copoly(3-hydroxyalkanoates) produced in the anaerobic-aerobic activated sludge process. Polymer International (1996), 39(3), 183-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available