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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:53 UTC
Update Date2021-10-13 06:26:52 UTC
HMDB IDHMDB0032797
Secondary Accession Numbers
  • HMDB32797
Metabolite 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. Based on a literature review a significant number of articles have been published on Jasmonic acid.
Structure
Data?1589310846
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 Weight210.2695
Monoisotopic Molecular Weight210.125594442
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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility742.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP10(2.36) g/LALOGPS
logP10(2.41) g/LChemAxon
logS10(-2.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.82731661259
DarkChem[M-H]-146.59531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Jasmonic acidCC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O3026.1Standard polar33892256
Jasmonic acidCC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O1680.6Standard non polar33892256
Jasmonic acidCC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O1714.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Jasmonic acid,1TMS,isomer #1CC/C=C\C[C@H]1C(=O)CC[C@@H]1CC(=O)O[Si](C)(C)C1780.3Semi standard non polar33892256
Jasmonic acid,1TMS,isomer #2CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O1865.7Semi standard non polar33892256
Jasmonic acid,1TMS,isomer #3CC/C=C\C[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O1838.4Semi standard non polar33892256
Jasmonic acid,2TMS,isomer #1CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C1875.3Semi standard non polar33892256
Jasmonic acid,2TMS,isomer #1CC/C=C\CC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C1903.8Standard non polar33892256
Jasmonic acid,2TMS,isomer #2CC/C=C\C[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C1864.3Semi standard non polar33892256
Jasmonic acid,2TMS,isomer #2CC/C=C\C[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C1907.1Standard non polar33892256
Jasmonic acid,1TBDMS,isomer #1CC/C=C\C[C@H]1C(=O)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C2017.5Semi standard non polar33892256
Jasmonic acid,1TBDMS,isomer #2CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O2117.4Semi standard non polar33892256
Jasmonic acid,1TBDMS,isomer #3CC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O2079.3Semi standard non polar33892256
Jasmonic acid,2TBDMS,isomer #1CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C2337.2Semi standard non polar33892256
Jasmonic acid,2TBDMS,isomer #1CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C2288.6Standard non polar33892256
Jasmonic acid,2TBDMS,isomer #2CC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C2310.3Semi standard non polar33892256
Jasmonic acid,2TBDMS,isomer #2CC/C=C\C[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)O[Si](C)(C)C(C)(C)C2182.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Jasmonic acid GC-MS (1 TMS)splash10-0gc1-3910000000-fc5414b89726602371072014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Jasmonic acid GC-MS (2 TMS)splash10-00di-1960000000-15b13e2686e63dbec8ac2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Jasmonic acid GC-MS (1 MEOX; 1 TMS)splash10-0fur-5920000000-56a3bfca05d9c2a0fb582014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Jasmonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-6900000000-6dbc88cef2dd120798d42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Jasmonic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fy9-9450000000-0d94fd142631685c4b7b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Jasmonic acid 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 - Jasmonic acid NA 35V, negative-QTOFsplash10-0a4i-9000000000-2d9af7143ec50cf2d0d02020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid LC-ESI-QTOF 35V, negative-QTOFsplash10-0a4i-9000000000-2d9af7143ec50cf2d0d02020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid NA , negative-QTOFsplash10-066r-2930000000-fa66a377eb1b1fca8f5c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid n/a 14V, negative-QTOFsplash10-014i-0900000000-6a243c2851549d3933a02020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid n/a 14V, negative-QTOFsplash10-0a4i-0090000000-32f15e4d1ce43554b3692020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 0V, negative-QTOFsplash10-0a4i-1090000000-0eea64532a321522940a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 1V, negative-QTOFsplash10-0a4i-1090000000-dcd76ae3b160ae066dac2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 1V, negative-QTOFsplash10-0a4i-1090000000-04497dd8bc966faba21c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 2V, negative-QTOFsplash10-0a4i-2090000000-1aa739b17227b81759642020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 2V, negative-QTOFsplash10-0a4i-2090000000-c3df319b32792e7026312020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 2V, negative-QTOFsplash10-0a4i-4090000000-aa4a7a821d19b44f0cd52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 3V, negative-QTOFsplash10-0a4i-5090000000-82f8a4dbefd75fc329722020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 3V, negative-QTOFsplash10-0a4i-6090000000-910ea32926dde4e482cb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 4V, negative-QTOFsplash10-0a4i-9080000000-56dfbbb726baa8bf1ca72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 5V, negative-QTOFsplash10-0a4i-9030000000-a7e12bbe5010ba971a9c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 6V, negative-QTOFsplash10-0a4i-9010000000-8184a91f4d8f167c84422020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 7V, negative-QTOFsplash10-0a4i-9000000000-dcce12c198d67bee2dbe2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 9V, negative-QTOFsplash10-0a4i-9000000000-47b37bf1431de1c71ac62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 13V, negative-QTOFsplash10-0a4i-9000000000-b8485c47ca16500d47c92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid n/a 14V, negative-QTOFsplash10-014i-0900000000-950facc2be1cf2c82d8a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid n/a 14V, negative-QTOFsplash10-001i-9000000000-e3fd77637016e123cdf02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid n/a 14V, negative-QTOFsplash10-000j-0900000000-040f7ed5f38f5823a12f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 8V, negative-QTOFsplash10-0a4i-2090400000-c723f443748062335ce62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 10V, negative-QTOFsplash10-0a4i-4090300000-040d95a6572bf3cbc6522020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Jasmonic acid Orbitrap 13V, negative-QTOFsplash10-0a4i-9051000000-1fa05530da91632d24172020-07-22HMDB team, MONAView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1459291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:20304987 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.