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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:28 UTC
Update Date2018-03-12 22:11:06 UTC
HMDB IDHMDB0036583
Secondary Accession Numbers
  • HMDB36583
Metabolite Identification
Common NameMethyl jasmonate
DescriptionMethyl jasmonate, also known as fema 3410, belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. Methyl jasmonate exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Methyl jasmonate has been primarily detected in urine. Within the cell, methyl jasmonate is primarily located in the membrane (predicted from logP) and cytoplasm. Methyl jasmonate is a floral, fresh, and jasmine tasting compound that can be found in a number of food items such as peach, french plantain, cherry tomato, and sweet cherry. This makes methyl jasmonate a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl esterChEBI
Methyl (-)-jasmonateChEBI
3-oxo-2-(2-Pentenyl)cyclopentaneacetate methyl esterGenerator
Methyl jasmonic acidGenerator
Methyl (-)-jasmonic acidGenerator
(-)-Jasmonic acid methyl esterHMDB
(-)-Methyl jasmonateHMDB
(3R,7R)-Methyl jasmonateHMDB
FEMA 3410HMDB
Jasmonic acid methyl esterHMDB
Methyl (2-pent-2-enyl-3-oxo-1-cyclopentyl)acetateHMDB
Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetateHMDB
Methyl cis-jasmonateHMDB
Z-Methyl jasmonoateHMDB
Methyl epijasmonateMeSH
Chemical FormulaC13H20O3
Average Molecular Weight224.2961
Monoisotopic Molecular Weight224.141244506
IUPAC Namemethyl 2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate
Traditional Name(-)-methyl jasmonate
CAS Registry Number1211-29-6
SMILES
CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O
InChI Identifier
InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1
InChI KeyGEWDNTWNSAZUDX-WQMVXFAESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentJasmonic acids
Alternative Parents
Substituents
  • Jasmonic acid
  • Methyl ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.62ALOGPS
logP2.56ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.33 m³·mol⁻¹ChemAxon
Polarizability25.03 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0036-6900000000-e2a3f1c368618b3e5f44View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aos-6900000000-0277b3467bce13283ff1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-1190000000-943fc4cad10af285a2beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-6910000000-b3add72153d54084414bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-1950000000-3c4a847eb81b54960c7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05rr-9710000000-500c8cdfcf8ef9dc46d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9100000000-6ebb500b1e7a59d8c7e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0490000000-c565f5ccca764f993aa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-4980000000-9c08c7091ed7d3a39d47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-8900000000-0e54fbfd7224fd3d6d2fView 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 IDFDB015494
KNApSAcK IDC00000219
Chemspider ID4519204
KEGG Compound IDC11512
BioCyc IDCPD1F-2
BiGG IDNot Available
Wikipedia LinkMethyl_jasmonate
METLIN IDNot Available
PubChem Compound5367719
PDB IDNot Available
ChEBI ID15929
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Umukoro S, Olugbemide AS: Antinociceptive effects of methyl jasmonate in experimental animals. J Nat Med. 2011 Jul;65(3-4):466-70. doi: 10.1007/s11418-011-0520-3. Epub 2011 Mar 9. [PubMed:21387099 ]
  2. Pi Y, Liao Z, Jiang K, Huang B, Deng Z, Zhao D, Zeng H, Sun X, Tang K: Molecular cloning, characterization and expression of a jasmonate biosynthetic pathway gene encoding allene oxide cyclase from Camptotheca acuminata. Biosci Rep. 2008 Dec;28(6):349-55. doi: 10.1042/BSR20060001. [PubMed:18847436 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.