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Showing metabocard for Methyl isobutyrate (HMDB0031249)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:41:52 UTC
Update Date2019-07-23 06:08:20 UTC
HMDB IDHMDB0031249
Secondary Accession Numbers
  • HMDB31249
Metabolite Identification
Common NameMethyl isobutyrate
DescriptionMethyl isobutyrate, also known as fema 2694, belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group. Methyl isobutyrate is an organic compound with the formula CH3O2CCH(CH3)2. Methyl isobutyrate is an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl isobutyrate is an apple, floral, and flower tasting compound. Outside of the human body, methyl isobutyrate has been detected, but not quantified in, several different foods, such as fruits, herbs and spices, pineapples, pomes, and potato. This could make methyl isobutyrate a potential biomarker for the consumption of these foods.
Structure
Data?1563862100
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Methyl isobutyric acidGenerator
2-Methyl-propanoic acid, methyl esterHMDB
FEMA 2694HMDB
Isobutyric acid methyl esterHMDB
Methyl 2-methylpropanoateHMDB
Methyl 2-methylpropionateHMDB
Methyl isobutanoateHMDB
Propanoic acid, 2-methyl-, methyl esterHMDB
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Namemethyl 2-methylpropanoate
Traditional Namemethyl isobutyrate
CAS Registry Number547-63-7
SMILES
COC(=O)C(C)C
InChI Identifier
InChI=1S/C5H10O2/c1-4(2)5(6)7-3/h4H,1-3H3
InChI KeyBHIWKHZACMWKOJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentMethyl esters
Alternative Parents
Substituents
  • Methyl ester
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-84.7 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility34.6 g/LALOGPS
logP1.2ALOGPS
logP1.17ChemAxon
logS-0.47ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.61 m³·mol⁻¹ChemAxon
Polarizability11.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-cd801699f9c2a557b43fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-3e969deccf54a3de9a05Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0fe0-9200000000-a852902f244e902cb44aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-036e1ab23d11bbe83602Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-cd801699f9c2a557b43fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-3e969deccf54a3de9a05Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0fe0-9200000000-a852902f244e902cb44aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-036e1ab23d11bbe83602Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-a10cecf41a27b2809df8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-4900000000-4158b3942dd80630a16cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fdo-9400000000-1fe485d0af82d169052bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4654b7b7e766fa0a4c2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-301f5de58f5b6678317eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4900000000-9dcbeff47e662d7a1842Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lki-9000000000-f7694af026d7ca6c20edSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ee4a74a8e58214633453Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS		 details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003279
KNApSAcK IDNot Available
Chemspider ID10571
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isobutyrate
METLIN IDNot Available
PubChem Compound11039
PDB IDNot Available
ChEBI ID73689
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .