Jasmonic acid (CHEM030252)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:46:03 UTC
Update Date2016-11-09 01:19:02 UTC
Accession NumberCHEM030252
Identification
Common NameJasmonic acid
ClassSmall Molecule
DescriptionAn oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass210.270 g/mol
Monoisotopic Mass210.126 g/mol
CAS Registry Number6894-38-8
IUPAC Name2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid
Traditional Namejasmonic acid
SMILESCC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gc1-3910000000-fc5414b8972660237107Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-1960000000-15b13e2686e63dbec8acSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0fur-5920000000-56a3bfca05d9c2a0fb58Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-6900000000-6dbc88cef2dd120798d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fy9-9450000000-0d94fd142631685c4b7bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - NA 35V, negativesplash10-0a4i-9000000000-2d9af7143ec50cf2d0d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0a4i-9000000000-2d9af7143ec50cf2d0d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , negativesplash10-066r-2930000000-fa66a377eb1b1fca8f5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 14V, negativesplash10-014i-0900000000-6a243c2851549d3933a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 14V, negativesplash10-0a4i-0090000000-32f15e4d1ce43554b369Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0a4i-1090000000-0eea64532a321522940aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0a4i-1090000000-dcd76ae3b160ae066dacSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0a4i-1090000000-04497dd8bc966faba21cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0a4i-2090000000-1aa739b17227b8175964Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0a4i-2090000000-c3df319b32792e702631Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0a4i-4090000000-aa4a7a821d19b44f0cd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0a4i-5090000000-82f8a4dbefd75fc32972Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0a4i-6090000000-910ea32926dde4e482cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4i-9080000000-56dfbbb726baa8bf1ca7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9030000000-a7e12bbe5010ba971a9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9010000000-8184a91f4d8f167c8442Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0a4i-9000000000-dcce12c198d67bee2dbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-0a4i-9000000000-47b37bf1431de1c71ac6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0a4i-9000000000-b8485c47ca16500d47c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1940000000-cbdd7749a0552b6dcb18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-9700000000-4b9efb60332c4d520667Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9100000000-e7e90e131d7ac7d27a35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0690000000-d03d837380060d855a00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3950000000-30695cc3cca6390fcaceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9400000000-c0d8ea2d3164bace07b2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032797
FooDB IDFDB015493
Phenol Explorer IDNot Available
KNApSAcK IDC00000218
BiGG IDNot Available
BioCyc IDCPD-734
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkJasmonic_acid
Chemspider ID4444606
ChEBI ID18292
PubChem Compound ID5281166
Kegg Compound IDC08491
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17470145
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19704561
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=28223489
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=33516967
5. Rossard S, Roblin G, Atanassova R: Ergosterol triggers characteristic elicitation steps in Beta vulgaris leaf tissues. J Exp Bot. 2010 Jun;61(6):1807-16. doi: 10.1093/jxb/erq047. Epub 2010 Mar 19.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. 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.
8. 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.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
11. The lipid handbook with CD-ROM