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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:36:37 UTC
Update Date2019-01-11 19:50:28 UTC
HMDB IDHMDB0035601
Secondary Accession Numbers
  • HMDB35601
Metabolite Identification
Common Name(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one
Description(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is found in citrus. (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one occurs in peppermint oil, green tea and bergamot oranges (Citrus bergamia).Jasmone is a natural organic compound extracted from the volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid that has the odor of jasmine. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture containing both forms, with the cis form predominating. Both forms have similar odors and chemical properties. (Wikipedia
Structure
Data?1547236228
Synonyms
ValueSource
cis-JasmoneKegg
(Z)-JasmoneHMDB
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8ci)HMDB
2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9ci)HMDB
3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-oneHMDB
cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneHMDB
JasmoneMeSH
Chemical FormulaC11H16O
Average Molecular Weight164.2441
Monoisotopic Molecular Weight164.120115134
IUPAC Name3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Traditional Namejasmone
CAS Registry Number488-10-8
SMILES
CC\C=C/CC1=C(C)CCC1=O
InChI Identifier
InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
InChI KeyXMLSXPIVAXONDL-PLNGDYQASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.7 g/LALOGPS
logP3.32ALOGPS
logP3.1ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.9 m³·mol⁻¹ChemAxon
Polarizability19.79 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9700000000-626f6beb94dae241c8a7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r6-9600000000-b7842817d55e1ef34cd5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9700000000-626f6beb94dae241c8a7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01r6-9600000000-b7842817d55e1ef34cd5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-6900000000-4ec9a03205a62c5db571View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-b3455ba1815cd60172a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-7900000000-df4da4ed2a4217531361View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9100000000-1ad974119b61c19d8fcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-54214296816474e67819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-9e2bcdc11fb8c55163abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9800000000-3aa25aca2cc0986b4e11View in MoNA
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
FoodDB IDFDB014294
KNApSAcK IDC00001313 C00029353
Chemspider ID1266012
KEGG Compound IDC08490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549018
PDB IDNot Available
ChEBI IDNot Available
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.. .