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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:30:08 UTC
Update Date2019-07-23 06:14:13 UTC
HMDB IDHMDB0033742
Secondary Accession Numbers
  • HMDB33742
Metabolite Identification
Common Name(S)-2-Methylbutanoic acid
Description(S)-2-Methylbutanoic acid is found in fats and oils. (S)-2-Methylbutanoic acid is isolated from many essential oils and other biol. sources.
Structure
Data?1563862453
Synonyms
ValueSource
(S)-alpha-Methylbutanoic acidChEBI
(S)-a-MethylbutanoateGenerator
(S)-a-Methylbutanoic acidGenerator
(S)-alpha-MethylbutanoateGenerator
(S)-α-methylbutanoateGenerator
(S)-α-methylbutanoic acidGenerator
(S)-2-MethylbutanoateGenerator
(+)-(S)-2-Methylbutanoic acidHMDB
(+)-2-Methylbutanoic acidHMDB
(+)-2-Methylbutyric acidHMDB
(+)-alpha-Methylbutyric acidHMDB
(2S)-2-Methylbutanoic acidHMDB
(S)-(+)-2-Methylbutyric acidHMDB
(S)-2-Methylbutyric acidHMDB
2-Methyl-(2S)-butanoic acidHMDB
2-Methyl-(S)-butanoic acidHMDB
Butyric acid, 2-methyl-, (S)- (8ci)HMDB
Butyric acid, 2-methyl-, L- (6ci)HMDB
S-(+)-2-Methylbutanoic acidHMDB
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Name(2S)-2-methylbutanoic acid
Traditional Name(S)-2-methylbutanoic acid
CAS Registry Number1730-91-2
SMILES
CC[C@H](C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1
InChI KeyWLAMNBDJUVNPJU-BYPYZUCNSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.18Not 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-79d087e0de5177254e25JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05dr-9200000000-d03c368f82e8aafbbf2eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-8900000000-5805fdbaf903d5c4fd44JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-2c0ab483ea6c382d58ebJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4194aff1e660af5a6473JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-f75d538fe0cfd19adf2bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9600000000-fa809749116e6af5c680JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-dd705ef710503eacd311JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected and Quantified735.913 +/- 226.276 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Normal
details
FecesDetected and Quantified1150 +/- 880 nmol/g wet fecesAdult (>18 years old)Female
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Treated celiac disease
details
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011870
KNApSAcK IDNot Available
Chemspider ID395556
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound448893
PDB IDSMB
ChEBI ID38655
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.