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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:05 UTC
Update Date2023-02-21 17:22:15 UTC
HMDB IDHMDB0032491
Secondary Accession Numbers
  • HMDB32491
Metabolite Identification
Common NamePrenyl isobutyrate
DescriptionPrenyl isobutyrate 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). Prenyl isobutyrate is a berry, butter, and fruity tasting compound. Based on a literature review very few articles have been published on Prenyl isobutyrate.
Structure
Data?1677000135
Synonyms
ValueSource
Prenyl isobutyric acidGenerator
3-Methylbut-2-enyl isobutyrateHMDB
Propanoic acid, 2-methyl-, 3-methyl-2-buten-1-yl esterHMDB
Propanoic acid, 2-methyl-, 3-methyl-2-butenyl esterHMDB
3-Methylbut-2-en-1-yl 2-methylpropanoic acidGenerator
Chemical FormulaC9H16O2
Average Molecular Weight156.2221
Monoisotopic Molecular Weight156.115029756
IUPAC Name3-methylbut-2-en-1-yl 2-methylpropanoate
Traditional Name3-methylbut-2-en-1-yl 2-methylpropanoate
CAS Registry Number76649-23-5
SMILES
CC(C)C(=O)OCC=C(C)C
InChI Identifier
InChI=1S/C9H16O2/c1-7(2)5-6-11-9(10)8(3)4/h5,8H,6H2,1-4H3
InChI KeyYSJHMPXIMIOXGU-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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.34 g/LALOGPS
logP2.96ALOGPS
logP2.53ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity45.73 m³·mol⁻¹ChemAxon
Polarizability18.58 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]+138.43331661259
DarkChem[M-H]-132.8431661259
DeepCCS[M+H]+140.830932474
DeepCCS[M-H]-138.09230932474
DeepCCS[M-2H]-174.39930932474
DeepCCS[M+Na]+149.84730932474
AllCCS[M+H]+135.432859911
AllCCS[M+H-H2O]+131.532859911
AllCCS[M+NH4]+139.032859911
AllCCS[M+Na]+140.032859911
AllCCS[M-H]-136.332859911
AllCCS[M+Na-2H]-138.432859911
AllCCS[M+HCOO]-140.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prenyl isobutyrateCC(C)C(=O)OCC=C(C)C1331.5Standard polar33892256
Prenyl isobutyrateCC(C)C(=O)OCC=C(C)C1010.7Standard non polar33892256
Prenyl isobutyrateCC(C)C(=O)OCC=C(C)C1065.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prenyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9000000000-5e709183ee493c546e352017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prenyl isobutyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 10V, Positive-QTOFsplash10-0aor-9800000000-367aae9a1139fe60c7d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Positive-QTOFsplash10-014i-9100000000-8ec13639477cdcbc9cd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Positive-QTOFsplash10-0603-9000000000-84b293b45aa3afdbe0a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 10V, Negative-QTOFsplash10-0a4i-6900000000-bbf81a5e204dcdd7ee182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Negative-QTOFsplash10-000i-9100000000-8b79b14d7f541ea9c02c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Negative-QTOFsplash10-00kr-9000000000-be6621fcec4a97563b342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 10V, Negative-QTOFsplash10-000i-9000000000-e4cb211981804e9150f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Negative-QTOFsplash10-000i-9000000000-f0d1d76a3ff0244e0bf02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Negative-QTOFsplash10-00dr-9000000000-870c94464becec2e26932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 10V, Positive-QTOFsplash10-014i-9000000000-455ac7e6cbb6b6b268452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 20V, Positive-QTOFsplash10-014l-9000000000-bafdab33b4d3558bdebf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prenyl isobutyrate 40V, Positive-QTOFsplash10-0006-9000000000-bcb4ebb7f9d789d208c62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010137
KNApSAcK IDNot Available
Chemspider ID151464
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound173535
PDB IDNot Available
ChEBI ID206353
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .