Showing Compound Card for Jasmonic acid (CDB005315)

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Record Information
Version1.0
Created at2020-04-17 19:30:53 UTC
Updated at2022-12-13 23:36:28 UTC
CannabisDB IDCDB005315
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameJasmonic acid
DescriptionJasmonic acid, also known as 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. Jasmonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Jasmonic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-Jasmonic acidChEBI
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetic acidChEBI
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetic acidChEBI
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetateChEBI
JasmonateChEBI
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetic acidKegg
(-)-JasmonateKegg
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetateGenerator
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetateGenerator
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetic acidGenerator
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetateGenerator
7-Epi-jasmonic acidMeSH
(Z)-trans-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acidPhytoBank
[1R-[1alpha,2beta(Z)]]-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acidPhytoBank
[1R-[1α,2β(Z)]]-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acidPhytoBank
(1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetic acidPhytoBank
(1R,2R)-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic acidPhytoBank
(1R,2R)-Jasmonic acidPhytoBank
(3R,7R)(-)-Jasmonic acidPhytoBank
JAPhytoBank
Chemical FormulaC12H18O3
Average Molecular Weight210.27
Monoisotopic Molecular Weight210.1256
IUPAC Name2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid
Traditional Namejasmonic acid
CAS Registry Number59366-47-1
SMILES
CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O
InChI Identifier
InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
InChI KeyZNJFBWYDHIGLCU-HWKXXFMVSA-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
  • Cyclic ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point160 °C at 0.7 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.36ALOGPS
logP2.41ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.56 m³·mol⁻¹ChemAxon
Polarizability22.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSJasmonic acid, 1 TMS, GC-MS Spectrumsplash10-0gc1-3910000000-fc5414b8972660237107Spectrum
GC-MSJasmonic acid, 2 TMS, GC-MS Spectrumsplash10-00di-1960000000-15b13e2686e63dbec8acSpectrum
GC-MSJasmonic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-0fur-5920000000-56a3bfca05d9c2a0fb58Spectrum
Predicted GC-MSJasmonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-6900000000-6dbc88cef2dd120798d4Spectrum
Predicted GC-MSJasmonic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fy9-9450000000-0d94fd142631685c4b7bSpectrum
Predicted GC-MSJasmonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA 35V, negativesplash10-0a4i-9000000000-2d9af7143ec50cf2d0d02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0a4i-9000000000-2d9af7143ec50cf2d0d02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , negativesplash10-066r-2930000000-fa66a377eb1b1fca8f5c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, negativesplash10-014i-0900000000-6a243c2851549d3933a02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, negativesplash10-0a4i-0090000000-32f15e4d1ce43554b3692020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0a4i-1090000000-0eea64532a321522940a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0a4i-1090000000-dcd76ae3b160ae066dac2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0a4i-1090000000-04497dd8bc966faba21c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0a4i-2090000000-1aa739b17227b81759642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0a4i-2090000000-c3df319b32792e7026312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0a4i-4090000000-aa4a7a821d19b44f0cd52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0a4i-5090000000-82f8a4dbefd75fc329722020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0a4i-6090000000-910ea32926dde4e482cb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4i-9080000000-56dfbbb726baa8bf1ca72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9030000000-a7e12bbe5010ba971a9c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9010000000-8184a91f4d8f167c84422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0a4i-9000000000-dcce12c198d67bee2dbe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-0a4i-9000000000-47b37bf1431de1c71ac62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0a4i-9000000000-b8485c47ca16500d47c92020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1940000000-cbdd7749a0552b6dcb182016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-9700000000-4b9efb60332c4d5206672016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9100000000-e7e90e131d7ac7d27a352016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0690000000-d03d837380060d855a002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3950000000-30695cc3cca6390fcace2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9400000000-c0d8ea2d3164bace07b22016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0112 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00883 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0266 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.00940 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0202 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00990 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0032797
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015493
KNApSAcK IDC00000218
Chemspider ID4444606
KEGG Compound IDC08491
BioCyc IDCPD-734
BiGG IDNot Available
Wikipedia LinkJasmonic_acid
METLIN IDNot Available
PubChem Compound5281166
PDB IDNot Available
ChEBI ID18292
References
General ReferencesNot Available