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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:28 UTC
Update Date2021-10-13 06:57:25 UTC
HMDB IDHMDB0036583
Secondary Accession Numbers
  • HMDB36583
Metabolite Identification
Common NameMethyl jasmonate
DescriptionMethyl jasmonate 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. Based on a literature review a significant number of articles have been published on Methyl jasmonate.
Structure
Data?1563862892
Synonyms
ValueSource
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl esterChEBI
Methyl (-)-jasmonateChEBI
(-)-Methyl jasmonateKegg
3-oxo-2-(2-Pentenyl)cyclopentaneacetate methyl esterGenerator
Methyl (-)-jasmonic acidGenerator
(-)-Methyl jasmonic acidGenerator
Methyl jasmonic acidGenerator
(-)-Jasmonic acid methyl esterHMDB
(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, HMDB
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
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point25 °CNot Available
Boiling Point110.00 °C. @ 0.20 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP2.945 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP10(2.62) g/LALOGPS
logP10(2.56) g/LChemAxon
logS10(-3.1) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.84831661259
DarkChem[M-H]-149.71431661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl jasmonate GC-MS (Non-derivatized)splash10-0036-6900000000-e2a3f1c368618b3e5f442014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl jasmonate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aos-6900000000-0277b3467bce13283ff12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl jasmonate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl jasmonate LC-ESI-QTOF , negative-QTOFsplash10-00di-1190000000-943fc4cad10af285a2be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl jasmonate LC-ESI-QTOF , negative-QTOFsplash10-002b-6910000000-b3add72153d54084414b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl jasmonate 30V, Negative-QTOFsplash10-002b-6910000000-b3add72153d54084414b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl jasmonate 30V, Positive-QTOFsplash10-002b-6910000000-f1bcd33a3f20473d55ab2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Positive-QTOFsplash10-004l-1950000000-3c4a847eb81b54960c7b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Positive-QTOFsplash10-05rr-9710000000-500c8cdfcf8ef9dc46d12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Positive-QTOFsplash10-0f9x-9100000000-6ebb500b1e7a59d8c7e82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Negative-QTOFsplash10-00di-0490000000-c565f5ccca764f993aa02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Negative-QTOFsplash10-00dl-4980000000-9c08c7091ed7d3a39d472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Negative-QTOFsplash10-006x-8900000000-0e54fbfd7224fd3d6d2f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Negative-QTOFsplash10-00di-8090000000-33319c51557d092716f42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Negative-QTOFsplash10-006x-9210000000-740f7074694405f5de2c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Negative-QTOFsplash10-0006-9200000000-25e9eab4222f102fe0572021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 10V, Positive-QTOFsplash10-0kea-2940000000-29e9828c7230abaacf6b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 20V, Positive-QTOFsplash10-053s-6900000000-04d6ddc8ffb62ec14cd62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl jasmonate 40V, Positive-QTOFsplash10-057l-9100000000-f913cbf151b98b42e7a82021-09-25Wishart 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 IDFDB015494
KNApSAcK IDC00000219
Chemspider ID4445210
KEGG Compound IDC11512
BioCyc IDCPD1F-2
BiGG IDNot Available
Wikipedia LinkMethyl_jasmonate
METLIN IDNot Available
PubChem Compound5367719
PDB IDNot Available
ChEBI ID15929
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1000141
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.