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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:53 UTC
Update Date2017-12-07 03:20:50 UTC
HMDB IDHMDB0032797
Secondary Accession Numbers
  • HMDB32797
Metabolite Identification
Common NameJasmonic acid
DescriptionJasmonic acid is found in apple. Esters are present in Jasminum grandiflorum (royal jasmine) and are responsible for its odour. Jasmonic acid is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway
Structure
Thumb
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
(-)-JasmonateGenerator
(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
7-Epi-jasmonic acidMeSH
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
DescriptionThis compound 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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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
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
Polarizability22.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gc1-3910000000-fc5414b8972660237107View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-1960000000-15b13e2686e63dbec8acView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0fur-5920000000-56a3bfca05d9c2a0fb58View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-6900000000-6dbc88cef2dd120798d4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fy9-9450000000-0d94fd142631685c4b7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1940000000-cbdd7749a0552b6dcb18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-9700000000-4b9efb60332c4d520667View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9100000000-e7e90e131d7ac7d27a35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0690000000-d03d837380060d855a00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3950000000-30695cc3cca6390fcaceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9400000000-c0d8ea2d3164bace07b2View in MoNA
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
FoodDB IDFDB015493
KNApSAcK IDC00000218
Chemspider ID4444606
KEGG Compound IDC08491
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkJasmonic_acid
METLIN IDNot Available
PubChem Compound5281166
PDB IDNot Available
ChEBI ID18292
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.