(4Z,9a)-9-(3-Methyl-2-butenoyloxy)-4,10(14)-oplopadien-3-one (CHEM028653)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:36:00 UTC
Update Date2016-11-09 01:18:44 UTC
Accession NumberCHEM028653
Identification
Common Name(4Z,9a)-9-(3-Methyl-2-butenoyloxy)-4,10(14)-oplopadien-3-one
ClassSmall Molecule
Description(4Z,9a)-9-(3-Methyl-2-butenoyloxy)-4,10(14)-oplopadien-3-one is found in tea. (4Z,9a)-9-(3-Methyl-2-butenoyloxy)-4,10(14)-oplopadien-3-one is a constituent of Tussilago farfara (coltsfoot)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1Z)-1-Ethylidene-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl 3-methylbut-2-enoic acidGenerator
Chemical FormulaC20H28O3
Average Molecular Mass316.435 g/mol
Monoisotopic Mass316.204 g/mol
CAS Registry Number237406-99-4
IUPAC Name(1Z)-1-ethylidene-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl 3-methylbut-2-enoate
Traditional Name(1Z)-1-ethylidene-7-isopropyl-4-methylidene-2-oxo-hexahydroinden-5-yl 3-methylbut-2-enoate
SMILESC\C=C1\C2C(CC1=O)C(=C)C(CC2C(C)C)OC(=O)C=C(C)C
InChI IdentifierInChI=1S/C20H28O3/c1-7-14-17(21)9-16-13(6)18(23-19(22)8-11(2)3)10-15(12(4)5)20(14)16/h7-8,12,15-16,18,20H,6,9-10H2,1-5H3/b14-7+
InChI KeyMZPCWAQWDXGSCO-VGOFMYFVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Oplopane sesquiterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0083 g/LALOGPS
logP4.85ALOGPS
logP4.67ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.49 m³·mol⁻¹ChemAxon
Polarizability36.27 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-9240000000-70b29e4726d6a3b8b7e9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5196000000-ca60437906a587456a1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9230000000-e8f421386907d15c42acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9310000000-e49296875f293a861352Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-2059000000-8a263e58edaa3041cfe8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4092000000-dad68aece585f97c69c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-9270000000-ab923411f9164223e197Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00vi-0940000000-018c2e2357609e8d8476Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0691000000-34c65b73511f54f1c63bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9720000000-fcd71a9075d69fc0301aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1029000000-146d87a2bbeb30ab2880Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-9085000000-6ff00e8b66c00c9f9b35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067i-9071000000-50432ba9db542ca06428Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034630
FooDB IDFDB013152
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013751
ChEBI IDNot Available
PubChem Compound ID131751595
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM