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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:45:08 UTC
Update Date2019-07-23 06:09:24 UTC
HMDB IDHMDB0031740
Secondary Accession Numbers
  • HMDB31740
Metabolite Identification
Common NameMethyl dihydrojasmonate
DescriptionMethyl dihydrojasmonate, also known as fema 3408 or hedione, 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. Methyl dihydrojasmonate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862163
Synonyms
ValueSource
Methyl dihydrojasmonic acidGenerator
(-)-Methyl dihydrojasmonateHMDB
(1R,2R)-Methyl dihydrojasmonateHMDB
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl esterHMDB
Dihydrojasmonic acid methyl esterHMDB
FEMA 3408HMDB
HedioneHMDB
KharismalHMDB
Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetateHMDB
Methyl (2-pentyl-3-oxocyclopentyl)acetateHMDB
Methyl (3-oxo-2-pentylcyclopentyl)acetateHMDB
Methyl 3-oxo-2-pentylcyclopentaneacetateHMDB
Methyl hydrojasmonateHMDB
Methyl trans-dihydrojasmonateHMDB
trans-(-)-HedioneHMDB
Methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetic acidGenerator
Chemical FormulaC13H22O3
Average Molecular Weight226.312
Monoisotopic Molecular Weight226.15689457
IUPAC Namemethyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate
Traditional Namemethyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate
CAS Registry Number24851-98-7
SMILES
CCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O
InChI Identifier
InChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3/t10-,11-/m1/s1
InChI KeyKVWWIYGFBYDJQC-GHMZBOCLSA-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
  • Methyl ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-10 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.56ALOGPS
logP2.92ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity62.21 m³·mol⁻¹ChemAxon
Polarizability26.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5a-6900000000-3a037dc37bb2f8297aa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0950000000-d91b264a1f9e1038cc00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05qa-9710000000-6a6d3e5275fe9178747aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053l-9100000000-30bb4dd7ae78c18a4b36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0590000000-485c2f69fcdbfe29dc24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-2960000000-ca65205581ae2e0aed1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxy-7900000000-789ffae3c13414a1f701Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008409
KNApSAcK IDNot Available
Chemspider ID92919
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl dihydrojasmonate
METLIN IDNot Available
PubChem Compound102861
PDB IDNot Available
ChEBI ID89741
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.