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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:45:08 UTC
Update Date2022-09-22 18:34:24 UTC
HMDB IDHMDB0031740
Secondary Accession Numbers
  • HMDB31740
Metabolite Identification
Common NameMethyl dihydrojasmonate
DescriptionMethyl 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. Based on a literature review a small amount of articles have been published on Methyl dihydrojasmonate.
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
Physiological effect
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-10 °CNot Available
Boiling Point109.00 to 112.00 °C. @ 0.20 mm HgThe Good Scents Company Information System
Water Solubility0.28 mg/mLNot Available
LogP2.653 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.34331661259
DarkChem[M-H]-157.61531661259
DeepCCS[M+H]+158.66430932474
DeepCCS[M-H]-156.30630932474
DeepCCS[M-2H]-189.19130932474
DeepCCS[M+Na]+164.75730932474
AllCCS[M+H]+155.732859911
AllCCS[M+H-H2O]+152.032859911
AllCCS[M+NH4]+159.032859911
AllCCS[M+Na]+160.032859911
AllCCS[M-H]-159.232859911
AllCCS[M+Na-2H]-160.032859911
AllCCS[M+HCOO]-161.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl dihydrojasmonateCCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O2378.0Standard polar33892256
Methyl dihydrojasmonateCCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O1623.5Standard non polar33892256
Methyl dihydrojasmonateCCCCC[C@@H]1[C@@H](CC(=O)OC)CCC1=O1663.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl dihydrojasmonate,1TMS,isomer #1CCCCCC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)OC1781.8Semi standard non polar33892256
Methyl dihydrojasmonate,1TMS,isomer #1CCCCCC1=C(O[Si](C)(C)C)CC[C@@H]1CC(=O)OC1778.8Standard non polar33892256
Methyl dihydrojasmonate,1TMS,isomer #2CCCCC[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)OC1763.4Semi standard non polar33892256
Methyl dihydrojasmonate,1TMS,isomer #2CCCCC[C@H]1C(O[Si](C)(C)C)=CC[C@@H]1CC(=O)OC1791.5Standard non polar33892256
Methyl dihydrojasmonate,1TBDMS,isomer #1CCCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)OC2000.8Semi standard non polar33892256
Methyl dihydrojasmonate,1TBDMS,isomer #1CCCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1CC(=O)OC1956.5Standard non polar33892256
Methyl dihydrojasmonate,1TBDMS,isomer #2CCCCC[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)OC1965.6Semi standard non polar33892256
Methyl dihydrojasmonate,1TBDMS,isomer #2CCCCC[C@H]1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]1CC(=O)OC1913.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl dihydrojasmonate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5a-6900000000-3a037dc37bb2f8297aa72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl dihydrojasmonate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 10V, Negative-QTOFsplash10-004i-0590000000-485c2f69fcdbfe29dc242017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 20V, Negative-QTOFsplash10-004l-2960000000-ca65205581ae2e0aed1b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 40V, Negative-QTOFsplash10-0fxy-7900000000-789ffae3c13414a1f7012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 10V, Negative-QTOFsplash10-004l-9080000000-732b5977d17ab527c0e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 20V, Negative-QTOFsplash10-0006-9110000000-19da6009553588ebb1b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 40V, Negative-QTOFsplash10-006x-9700000000-f3e2a11570c24a600db52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 10V, Positive-QTOFsplash10-004j-0950000000-d91b264a1f9e1038cc002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 20V, Positive-QTOFsplash10-05qa-9710000000-6a6d3e5275fe9178747a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 40V, Positive-QTOFsplash10-053l-9100000000-30bb4dd7ae78c18a4b362017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 10V, Positive-QTOFsplash10-056r-2970000000-5a6a3885b6573f5c38a92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 20V, Positive-QTOFsplash10-057s-8920000000-9e55f6d35e44847d4e372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl dihydrojasmonate 40V, Positive-QTOFsplash10-001l-9000000000-1c2a95e6f01527b3c1042021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008409
KNApSAcK IDC00051556
Chemspider ID1376701
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
MarkerDB IDNot Available
Good Scents IDrw1015272
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.