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Jasmonic acid (FDB015493)

Record Information
Version1.0
Creation date2010-04-08 22:11:52 UTC
Update date2020-09-17 15:41:51 UTC
Primary IDFDB015493
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number59366-47-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not 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
Polarizability22.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H18O3
IUPAC name2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid
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
Isomeric SMILESCC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O
Average Molecular Weight210.2695
Monoisotopic Molecular Weight210.125594442
Classification
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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.55%; H 8.63%; O 22.83%DFC
Melting PointNot Available
Boiling PointBp0.001 125°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -83.5 (c, 0.97 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn19D 1.4885DFC
Spectra
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
ChemSpider ID4444606
ChEMBL IDNot Available
KEGG Compound IDC08491
Pubchem Compound ID5281166
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32797
CRC / DFC (Dictionary of Food Compounds) IDKCT55-C:KCT55-C
EAFUS IDNot Available
Dr. Duke IDJASMONIC-ACID|(-)-JASMONIC-ACID
BIGG IDNot Available
KNApSAcK IDC00000218
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDJasmonic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
fungicide24127 A substance used to destroy fungal pests.DUKE
phytohormonal26158 A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).