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Record Information
Version1.0
Created at2020-11-23 19:40:27 UTC
Updated at2021-08-12 19:52:09 UTC
NP-MRD IDNP0002788
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl jasmonate
Provided ByBMRBBMRB logo
DescriptionMethyl 2-[(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetate 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 is found in Arabidopsis thaliana, Artemisia absinthium , Artemisia tridentata, Camellia japonica , Camellia sasanqua , Camellia sinensis , Chlorella sp., Citrus limon , Eschscholzia californica , Ficus superba, Jasminum grandiflorum , Malva sylvestris and Rauvolfia canescens. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on methyl 2-[(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetate (PMID: 34378779) (PMID: 34371628) (PMID: 34366598) (PMID: 34363225).
Structure
Thumb
Synonyms
ValueSource
Methyl 2-[(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetic acidGenerator
Methyl jasmonic acidGenerator
Jasmonic acid methyl esterMeSH
3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl esterMeSH
Methyl epijasmonateMeSH
Chemical FormulaC13H20O3
Average Mass224.3000 Da
Monoisotopic Mass224.14124 Da
IUPAC Namemethyl 2-[(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetate
Traditional Namemethyl [(1R,2R)-3-oxo-2-[(2E)-pent-2-en-1-yl]cyclopentyl]acetate
CAS Registry NumberNot Available
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-XKFHPXPTSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Artemisia absinthiumPlant
Artemisia tridentataPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Camellia japonicaPlant
Camellia sasanquaPlant
Camellia sinensisPlant
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chlorella sp.Plant
Citrus limonPlant
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Eschscholzia californicaPlant
Ficus superbaPlant
Gallus gallusFooDB
Jasminum grandiflorumPlant
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Malva sylvestrisPlant
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha x piperitaFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Rauvolfia canescensPlant
Salvia rosmarinusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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 DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.56ChemAxon
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
Polarizability25.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4937273
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6432008
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Agnello AM, Combs DB, Filgueiras CC, Willett DS, Mafra-Neto A: Reduced Infestation by Xylosandrus germanus (Coleoptera: Curculionidae: Scolytinae) in Apple Trees Treated with Host Plant Defense Compounds. J Econ Entomol. 2021 Aug 11. pii: 6347851. doi: 10.1093/jee/toab153. [PubMed:34378779 ]
  3. Repkina N, Ignatenko A, Holoptseva E, MiszalskI Z, Kaszycki P, Talanova V: Exogenous Methyl Jasmonate Improves Cold Tolerance with Parallel Induction of Two Cold-Regulated (COR) Genes Expression in Triticum aestivum L. Plants (Basel). 2021 Jul 12;10(7). pii: plants10071421. doi: 10.3390/plants10071421. [PubMed:34371628 ]
  4. Saral A, Kanekar S, Koul KK, Bhagyawant SS: Plant growth promoting bacteria induce anti-quorum-sensing substances in chickpea legume seedling bioassay. Physiol Mol Biol Plants. 2021 Jul;27(7):1577-1595. doi: 10.1007/s12298-021-01034-x. Epub 2021 Jul 17. [PubMed:34366598 ]
  5. Manzoor MA, Guohui L, Muhammad A, Han W, Wenlong H, Yang Z, Xinya W, Yu Z, Xiaofeng F, Qing J, Shafique MS, Yongping C: Genome-wide investigation and comparative analysis of MATE gene family in Rosaceae species and their regulatory role in abiotic stress responses in Chinese pear (Pyrus bretschneideri). Physiol Plant. 2021 Aug 6. doi: 10.1111/ppl.13511. [PubMed:34363225 ]