Np mrd loader

Record Information
Version2.0
Created at2022-09-09 15:06:05 UTC
Updated at2025-02-11 15:48:43 UTC
NP-MRD IDNP0286499
Natural Product DOIhttps://doi.org/10.57994/2863
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-methyl 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. A jasmonate ester that is the methyl ester of jasmonic acid. Methyl jasmonate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methyl jasmonate is a floral, fresh, and jasmine tasting compound. Outside of the human body, Methyl jasmonate is found, on average, in the highest concentration within peppermints. Methyl jasmonate has also been detected, but not quantified in, several different foods, such as onion-family vegetables, lima beans, sweet rowanberries, alaska wild rhubarbs, and brassicas. (-)-methyl jasmonate is found in Arabidopsis thaliana, Artemisia absinthium and Citrus limon. (-)-methyl jasmonate was first documented in 2006 (PMID: 17043086). This could make methyl jasmonate a potential biomarker for the consumption of these foods (PMID: 24497113) (PMID: 18038760) (PMID: 21387099) (PMID: 18847436).
Structure
Thumb
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 epijasmonateHMDB
Chemical FormulaC13H20O3
Average Mass224.2961 Da
Monoisotopic Mass224.14124 Da
IUPAC Namemethyl 2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate
Traditional Name(-)-methyl jasmonate
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-WQMVXFAESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CDCl3, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaLOTUS Database
Artemisia absinthiumLOTUS Database
Citrus limonLOTUS Database
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
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
logP2.62ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036583
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
Good Scents IDNot Available
References
General References
  1. Carvacho HB, Perez C, Zuniga G, Mahn A: Effect of methyl jasmonate, sodium selenate and chitosan as exogenous elicitors on the phenolic compounds profile of broccoli sprouts. J Sci Food Agric. 2014 Sep;94(12):2555-61. doi: 10.1002/jsfa.6596. Epub 2014 Mar 18. [PubMed:24497113 ]
  2. Collen J, Herve C, Guisle-Marsollier I, Leger JJ, Boyen C: Expression profiling of Chondrus crispus (Rhodophyta) after exposure to methyl jasmonate. J Exp Bot. 2006;57(14):3869-81. doi: 10.1093/jxb/erl171. Epub 2006 Oct 16. [PubMed:17043086 ]
  3. Ezekwudo DE, Wang RC, Elegbede JA: Methyl jasmonate induced apoptosis in human prostate carcinoma cells via 5-lipoxygenase dependent pathway. J Exp Ther Oncol. 2007;6(4):267-77. [PubMed:18038760 ]
  4. 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 ]
  5. 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 ]
  6. LOTUS database [Link]