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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:57:31 UTC
Update Date2019-07-23 06:15:21 UTC
HMDB IDHMDB0034164
Secondary Accession Numbers
  • HMDB34164
Metabolite Identification
Common Name3-Methylbutyl propanoate
Description3-Methylbutyl propanoate, also known as isopentyl propionate or 3-methylbutyl propionic acid, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). 3-Methylbutyl propanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Methylbutyl propanoate is a sweet, banana, and bitter. Outside of the human body, 3-methylbutyl propanoate has been detected, but not quantified in, apples and roman camomiles. This could make 3-methylbutyl propanoate a potential biomarker for the consumption of these foods. A propanoate ester of isoamylol.
Structure
Data?1563862521
Synonyms
ValueSource
3-Methylbutyl propionateChEBI
Isopentyl propanoateChEBI
Isopentyl propionateChEBI
3-Methylbutyl propionic acidGenerator
Isopentyl propanoic acidGenerator
Isopentyl propionic acidGenerator
3-Methylbutyl propanoic acidGenerator
1-Butanol, 3-methyl-, 1-propanoateHMDB
1-Butanol, 3-methyl-, propanoateHMDB
3-Methyl-1-butyl propanoateHMDB
Dioleyl maleateHMDB
FEMA 2082HMDB
Iso-amyl N-propionateHMDB
Iso-pentyl propionateHMDB
Isoamyl propanoateHMDB
Isoamyl propionateHMDB
Isopentyl alcohol, propionateHMDB
Propionic acid, isopentyl esterHMDB
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Name3-methylbutyl propanoate
Traditional Name3-methylbutyl propanoate
CAS Registry Number105-68-0
SMILES
CCC(=O)OCCC(C)C
InChI Identifier
InChI=1S/C8H16O2/c1-4-8(9)10-6-5-7(2)3/h7H,4-6H2,1-3H3
InChI KeyXAOGXQMKWQFZEM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Carboxylic acid 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

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.42 g/LALOGPS
logP2.63ALOGPS
logP2.23ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.46 m³·mol⁻¹ChemAxon
Polarizability17.29 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)splash10-0adi-9000000000-d33d7fd534a8c6063d88Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0adi-9000000000-d33d7fd534a8c6063d88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-9f372b9db0d8d1159bc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-7900000000-0b05bc06211abe3466dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9100000000-4c74cc998be99116996bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-fe83b40c7605f1868e49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-9700000000-ae6e18986cce1b35a842Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9100000000-89d9c9e23cf814762586Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-beb3655c08cad2b4d3ceSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDFDB012450
KNApSAcK IDNot Available
Chemspider ID7484
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7772
PDB IDNot Available
ChEBI ID87419
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.. .