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Record Information
Version3.6
Creation Date2006-05-22 14:17:39 UTC
Update Date2016-08-22 20:07:50 UTC
HMDB IDHMDB02176
Secondary Accession NumbersNone
Metabolite Identification
Common NameEthylmethylacetic acid
DescriptionEthylmethylacetic acid is a carboxylic acid found in low amounts in normal humans (PMID 3372640 ). It has been described in the urine of individuals with 2-ethylhydracrylic aciduria associated with short/branched-chain acyl-CoA dehydrogenase deficiency (due to ACADSB gene mutations, OMIM 600301 ) (PMID 15615815 ).
Structure
Thumb
Synonyms
ValueSource
2-Methybutyric acidChEBI
alpha-Methyl butyric acidChEBI
alpha-Methylbutyric acidChEBI
Butane-2-carboxylic acidChEBI
Ethylmethylacetic acidChEBI
Methylethylacetic acidChEBI
2-MethybutyrateGenerator
2-MethylbutyrateGenerator
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
EthylmethylacetateGenerator
MethylethylacetateGenerator
(+/-)-2-methylbutyrateHMDB
(+/-)-2-methylbutyric acidHMDB
2-EthylpropionateHMDB
2-Ethylpropionic acidHMDB
2-Methyl butyrateHMDB
2-Methyl butyric acidHMDB
2-MethylbutanoateHMDB
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
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Name2-methylbutanoic acid
Traditional Name(+-)-2-methylbutyrate
CAS Registry Number116-53-0
SMILES
CCC(C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyInChIKey=WLAMNBDJUVNPJU-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility45 mg/mL at 20 °CNot Available
LogP1.18HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility57.2 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.45 m3·mol-1ChemAxon
Polarizability10.98 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-05i3-9000000000-1b5a036458bffab2edb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-9500000000-015593bb5625d47062e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-9cefc93a02ed409afaa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c09f00d4b395429c15fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-91099c4563c2a38048c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9500000000-614d914711126947b2ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-0c48b735fe7cb3bd438fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-05i0-9000000000-5202133990304f535e3eView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified735.913 +/- 226.276 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified8.04 +/- 7.66 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.0097 nmol/mmol creatinineChildren (1-13 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008135
KNApSAcK IDNot Available
Chemspider ID8012
KEGG Compound IDC18319
BioCyc IDBENZYL-2R3S-2-METHYL-3-HYDROXYBUTANOA
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02176
Metagene LinkHMDB02176
METLIN ID6528
PubChem Compound8314
PDB IDNot Available
ChEBI ID37070
References
Synthesis ReferenceBueding, Ernest; Yale, Helen W. Production of a-methylbutyric acid by bacteria-free Ascaris lumbricoides. Journal of Biological Chemistry (1951), 193 411-23.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [15615815 ]
  2. 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. [3372640 ]