2-METHYLBUTYRIC ACID (CHEM006538)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:14:58 UTC
Update Date2016-10-28 10:02:00 UTC
Accession NumberCHEM006538
Identification
Common Name2-METHYLBUTYRIC ACID
ClassSmall Molecule
DescriptionA methylbutyric acid comprising a butyric acid core carrying a 2-methyl substituent. Produced from amino acid leucine during nutrient starvation in bacteria.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methybutyric acidChEBI
alpha-Methyl butyric acidChEBI
alpha-Methylbutyric acidChEBI
Butane-2-carboxylic acidChEBI
Methylethylacetic acidChEBI
2-Methylbutyric acidKegg
2-MethybutyrateGenerator
a-Methyl butyrateGenerator
a-Methyl butyric acidGenerator
alpha-Methyl butyrateGenerator
Α-methyl butyrateGenerator
Α-methyl butyric acidGenerator
a-MethylbutyrateGenerator
a-Methylbutyric acidGenerator
alpha-MethylbutyrateGenerator
Α-methylbutyrateGenerator
Α-methylbutyric acidGenerator
Butane-2-carboxylateGenerator
MethylethylacetateGenerator
2-MethylbutyrateGenerator
EthylmethylacetateGenerator
(+/-)-2-methylbutyrateHMDB
(+/-)-2-methylbutyric acidHMDB
2-EthylpropionateHMDB
2-Ethylpropionic acidHMDB
2-Methyl butyrateHMDB
2-Methyl butyric acidHMDB
2-MethylbutanoateHMDB, Generator
2-Methylbutanoic acidHMDB
D-2-Methyl butyrateHMDB
D-2-Methyl butyric acidHMDB
DL-2-Methy butyrateHMDB
DL-2-Methy butyric acidHMDB
DL-2-MethylbutyrateHMDB
DL-2-Methylbutyric acidHMDB
2-Methylbutyrate, (+-)-isomerMeSH, HMDB
2-Methylbutyrate, sodium saltMeSH, HMDB
RS-2-MethylbutyrateMeSH, HMDB
Ethylmethylacetic acidChEBI
Chemical FormulaC5H10O2
Average Molecular Mass102.132 g/mol
Monoisotopic Mass102.068 g/mol
CAS Registry Number116-53-0
IUPAC Name2-methylbutanoic acid
Traditional Name(+-)-2-methylbutyrate
SMILESCCC(C)C(O)=O
InChI IdentifierInChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyWLAMNBDJUVNPJU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility57.2 g/LALOGPS
logP1.47ALOGPS
logP1.46ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.45 m³·mol⁻¹ChemAxon
Polarizability10.98 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-9000000000-0aaa78177c0a6f4e0f30Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-9000000000-0aaa78177c0a6f4e0f30Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-2909ffab0f5a63851edfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05dr-9200000000-d03c368f82e8aafbbf2eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-05i3-9000000000-1b5a036458bffab2edb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-4c159e60dacc58e6ba98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-3de63f631f358f44d663Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-49980d35bd5bcf94041bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-9500000000-ebceed22ebf0c3f30cbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-ee8b144eb008ebfb745cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-b0c600bc4b289c4f5f6dSpectrum
MSMass Spectrum (Electron Ionization)splash10-05i0-9000000000-5202133990304f535e3eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002176
FooDB IDFDB008135
Phenol Explorer IDNot Available
KNApSAcK IDC00029461
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6528
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8012
ChEBI ID37070
PubChem Compound ID8314
Kegg Compound IDC18319
YMDB IDYMDB01587
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15615815
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16751541
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18828792
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22202876
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3372640
6. Bueding, Ernest; Yale, Helen W. Production of a-methylbutyric acid by bacteria-free Ascaris lumbricoides. Journal of Biological Chemistry (1951), 193 411-23.
7. Bueding, Ernest; Yale, Helen W. Production of a-methylbutyric acid by bacteria-free Ascaris lumbricoides. Journal of Biological Chemistry (1951), 193 411-23.
8. Schatowitz B, Gercken G: Simultaneous determination of C2-C22 non-esterified fatty acids and other metabolically relevant carboxylic acids in biological material by gas chromatography of their benzyl esters. J Chromatogr. 1988 Mar 18;425(2):257-68.
9. Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22.