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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 01:45:30 UTC
Update Date2019-07-23 06:31:48 UTC
HMDB IDHMDB0040221
Secondary Accession Numbers
  • HMDB40221
Metabolite Identification
Common NameIsoamyl butyrate
DescriptionIsoamyl butyrate, also known as isopentyl butanoate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Isoamyl butyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isoamyl butyrate is a potentially toxic compound.
Structure
Data?1563863508
Synonyms
ValueSource
Butyric acid isopentyl esterChEBI
Isoamyl butanoateChEBI
Isopentyl butanoateChEBI
Isopentyl butyrateChEBI
Butyrate isopentyl esterGenerator
Isoamyl butanoic acidGenerator
Isopentyl butanoic acidGenerator
Isopentyl butyric acidGenerator
Isoamyl butyric acidGenerator
3-Methyl-1-butyl butanoateHMDB
3-Methylbutyl butanoateHMDB
3-Methylbutyl butyrateHMDB
Butanoic acid, 3-methylbutyl esterHMDB
Butyric acid isoamylesterHMDB
Butyric acid, isopentyl esterHMDB
Isoamyl butylateHMDB
Isoamyl-N-butyrateHMDB
Isopentyl alcohol, butyrateHMDB
Isopentyl-N-butyrateHMDB
3-Methylbutyl butyric acidGenerator
Chemical FormulaC9H18O2
Average Molecular Weight158.238
Monoisotopic Molecular Weight158.13067982
IUPAC Name3-methylbutyl butanoate
Traditional Nameisopentyl butanoate
CAS Registry Number106-27-4
SMILES
CCCC(=O)OCCC(C)C
InChI Identifier
InChI=1S/C9H18O2/c1-4-5-9(10)11-7-6-8(2)3/h8H,4-7H2,1-3H3
InChI KeyPQLMXFQTAMDXIZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • 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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-73.2 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP3ALOGPS
logP2.68ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.06 m³·mol⁻¹ChemAxon
Polarizability19.15 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)splash10-00dl-9000000000-be743bf025ce1c0dc836Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9000000000-518fbdd189797b447c9eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9000000000-84f324a87c41b088fe0bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9000000000-be743bf025ce1c0dc836Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9000000000-518fbdd189797b447c9eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9000000000-84f324a87c41b088fe0bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-ca7737b2c3b31c24315fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-7900000000-fc5d5da4c39a811cfdfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-0d00e86809eeaef20834Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-aa69778b86e4cc73b075Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-9700000000-aaab94c97872be613736Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-9100000000-6b639a9651d84b1a2f4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-224958884fe5e9847ccfSpectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9000000000-c2b5552462a028ba11f2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Female
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Adult (>18 years old)Female
Nonalcoholic fatty liver disease
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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019935
KNApSAcK IDNot Available
Chemspider ID7507
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7795
PDB IDNot Available
ChEBI ID87422
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.