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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:31:41 UTC
Update Date2023-02-21 17:26:52 UTC
HMDB IDHMDB0039159
Secondary Accession Numbers
  • HMDB39159
Metabolite Identification
Common NameBovolide
DescriptionBovolide belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Bovolide is a herbal, minty, and spicy tasting compound. Bovolide is found, on average, in the highest concentration within peppermints (Mentha X piperita). Bovolide has also been detected, but not quantified in, herbs and spices. This could make bovolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Bovolide.
Structure
Data?1677000412
Synonyms
ValueSource
3,4-Dimethyl-5-pentylidene-2(5H)-furanoneHMDB
Chemical FormulaC11H16O2
Average Molecular Weight180.2435
Monoisotopic Molecular Weight180.115029756
IUPAC Name(5E)-3,4-dimethyl-5-pentylidene-2,5-dihydrofuran-2-one
Traditional Name(5E)-3,4-dimethyl-5-pentylidenefuran-2-one
CAS Registry Number774-64-1
SMILES
CCCC\C=C1\OC(=O)C(C)=C1C
InChI Identifier
InChI=1S/C11H16O2/c1-4-5-6-7-10-8(2)9(3)11(12)13-10/h7H,4-6H2,1-3H3/b10-7+
InChI KeyMTQPZHNZYWAXEH-JXMROGBWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Enol ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point302.00 to 303.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility194.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.029 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.01 g/LALOGPS
logP3.54ALOGPS
logP3.12ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.13 m³·mol⁻¹ChemAxon
Polarizability21.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.0131661259
DarkChem[M-H]-144.02331661259
DeepCCS[M+H]+146.63230932474
DeepCCS[M-H]-143.71730932474
DeepCCS[M-2H]-179.99430932474
DeepCCS[M+Na]+155.53230932474
AllCCS[M+H]+140.932859911
AllCCS[M+H-H2O]+136.732859911
AllCCS[M+NH4]+144.832859911
AllCCS[M+Na]+146.032859911
AllCCS[M-H]-145.332859911
AllCCS[M+Na-2H]-146.432859911
AllCCS[M+HCOO]-147.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BovolideCCCC\C=C1\OC(=O)C(C)=C1C2174.7Standard polar33892256
BovolideCCCC\C=C1\OC(=O)C(C)=C1C1512.9Standard non polar33892256
BovolideCCCC\C=C1\OC(=O)C(C)=C1C1481.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bovolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-057i-9500000000-e3183d3c556d5cc7527d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bovolide 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 - Bovolide 10V, Positive-QTOFsplash10-001i-2900000000-8e44886d59258d1063342016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 20V, Positive-QTOFsplash10-0bt9-3900000000-7207668bad77bc5bfb422016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 40V, Positive-QTOFsplash10-1003-9000000000-af515284651118595fa62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 10V, Negative-QTOFsplash10-004i-1900000000-920a777f1fb60f9a2a692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 20V, Negative-QTOFsplash10-004r-2900000000-698fb3007eb2b1444fd02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 40V, Negative-QTOFsplash10-014i-9500000000-613857f18fd30f3b6aa82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 10V, Positive-QTOFsplash10-001i-1900000000-6a9684e2de2accc7e3152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 20V, Positive-QTOFsplash10-004i-8900000000-f1a1f074c3c154470e562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 40V, Positive-QTOFsplash10-0kdl-9100000000-08eecdd16b72748af7752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 10V, Negative-QTOFsplash10-004i-0900000000-ed614b6bd089f6f9641a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 20V, Negative-QTOFsplash10-004i-1900000000-8da14bba14d286291c392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bovolide 40V, Negative-QTOFsplash10-00tr-6900000000-55331dd2b26426f969922021-09-22Wishart 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
  • 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 IDFDB018683
KNApSAcK IDC00044813
Chemspider ID4938397
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6433214
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1428301
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.. .