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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 01:45:30 UTC
Update Date2022-03-07 02:56:31 UTC
HMDB IDHMDB0040221
Secondary Accession Numbers
  • HMDB40221
Metabolite Identification
Common NameIsoamyl butyrate
DescriptionIsoamyl butyrate, also known as isopentyl butanoate, is the butanoate ester of isoamylol. It derives from an isoamylol. Isoamyl butyrate 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. It has a role as a metabolite.
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

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-73.2 °CNot Available
Boiling Point179.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility118 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP3.250The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.34531661259
DarkChem[M-H]-134.47431661259
DeepCCS[M+H]+139.26130932474
DeepCCS[M-H]-136.38230932474
DeepCCS[M-2H]-172.97430932474
DeepCCS[M+Na]+148.42630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isoamyl butyrateCCCC(=O)OCCC(C)C1269.6Standard polar33892256
Isoamyl butyrateCCCC(=O)OCCC(C)C1036.6Standard non polar33892256
Isoamyl butyrateCCCC(=O)OCCC(C)C1075.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isoamyl butyrate EI-B (Non-derivatized)splash10-00dl-9000000000-be743bf025ce1c0dc8362017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl butyrate EI-B (Non-derivatized)splash10-00dl-9000000000-518fbdd189797b447c9e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl butyrate EI-B (Non-derivatized)splash10-00di-9000000000-84f324a87c41b088fe0b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl butyrate EI-B (Non-derivatized)splash10-00dl-9000000000-be743bf025ce1c0dc8362018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl butyrate EI-B (Non-derivatized)splash10-00dl-9000000000-518fbdd189797b447c9e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoamyl butyrate EI-B (Non-derivatized)splash10-00di-9000000000-84f324a87c41b088fe0b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl butyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-ca7737b2c3b31c24315f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamyl butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9000000000-c2b5552462a028ba11f22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 10V, Positive-QTOFsplash10-0ab9-7900000000-fc5d5da4c39a811cfdfd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 20V, Positive-QTOFsplash10-00di-9100000000-0d00e86809eeaef208342016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 40V, Positive-QTOFsplash10-05fu-9000000000-aa69778b86e4cc73b0752016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 10V, Negative-QTOFsplash10-0aor-9700000000-aaab94c97872be6137362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 20V, Negative-QTOFsplash10-00kr-9100000000-6b639a9651d84b1a2f4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 40V, Negative-QTOFsplash10-014l-9000000000-224958884fe5e9847ccf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 10V, Negative-QTOFsplash10-000i-9000000000-7b29cd57613420db0e312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 20V, Negative-QTOFsplash10-000i-9000000000-1237720a92a04d5cf9512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 40V, Negative-QTOFsplash10-014i-9000000000-0bbbb863de09ed47dbdf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 10V, Positive-QTOFsplash10-00di-9000000000-6323d067d73b0b4350d52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 20V, Positive-QTOFsplash10-05fr-9000000000-98a6d74da614b95857812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamyl butyrate 40V, Positive-QTOFsplash10-0006-9000000000-8ebd03e4939c0037677f2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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)Female
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)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
MarkerDB IDNot Available
Good Scents IDrw1006752
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.