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Record Information
Created at2022-03-17 20:44:12 UTC
Updated at2022-03-17 20:44:12 UTC
NP-MRD IDNP0047682
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrojasmonic acid
DescriptionDihydrojasmonic acid, also known as dihydrojasmonate, 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. Dihydrojasmonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydrojasmonic acid has been detected, but not quantified in, several different foods, such as broad beans, cereals and cereal products, pulses, and ryes. Dihydrojasmonic acid is found in Lasiodiplodia theobromae, Secale cereale and Vicia faba,Secale cereale. It was first documented in 2000 (PMID: 11413487). This could make dihydrojasmonic acid a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
(-)-9,10-Dihydrojasmonic acidHMDB
(-)-Dihydrojasmonic acidHMDB
2-[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acidHMDB
3-oxo-2-Pentyl-(1R-trans)-cyclopentaneacetic acidHMDB
9,10-Dihydrojasmonic acidHMDB
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, (1R,2R)- (9ci)HMDB
[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acidHMDB
Chemical FormulaC12H20O3
Average Mass212.2854 Da
Monoisotopic Mass212.14124 Da
IUPAC Name2-(3-oxo-2-pentylcyclopentyl)acetic acid
Traditional Name(3-oxo-2-pentylcyclopentyl)acetic acid
CAS Registry Number98674-52-3
InChI Identifier
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species of Origin
Species NameSourceReference
Lasiodiplodia theobromaeLOTUS Database
Secale cerealePlant
Vicia fabaFooDB
Vicia faba,Secale cerealePlant
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
  • 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 DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
pKa (Strongest Acidic)4.77ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity57.44 m³·mol⁻¹ChemAxon
Polarizability24.08 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011689
KNApSAcK IDC00000225
Chemspider ID96397
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107126
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]