4-Methoxycinnamoyloleanolic acid methyl ester (CHEM027623)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:51:46 UTC
Update Date2016-11-09 01:18:29 UTC
Accession NumberCHEM027623
Identification
Common Name4-Methoxycinnamoyloleanolic acid methyl ester
ClassSmall Molecule
Description4-Methoxycinnamoyloleanolic acid methyl ester is a constituent of Eucalyptus globulus (Tasmanian blue gum).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Methoxycinnamoyloleanolate methyl esterGenerator
Methyl 10-{[3-(4-methoxyphenyl)prop-2-enoyl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidHMDB
Chemical FormulaC41H58O5
Average Molecular Mass630.896 g/mol
Monoisotopic Mass630.428 g/mol
CAS Registry Number189140-50-9
IUPAC Namemethyl 10-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
Traditional Namemethyl 10-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate
SMILESCOC(=O)C12CCC(C)(C)CC1C1=CCC3C4(C)CCC(OC(=O)\C=C\C5=CC=C(OC)C=C5)C(C)(C)C4CCC3(C)C1(C)CC2
InChI IdentifierInChI=1S/C41H58O5/c1-36(2)22-24-41(35(43)45-9)25-23-39(6)29(30(41)26-36)15-16-32-38(5)20-19-33(37(3,4)31(38)18-21-40(32,39)7)46-34(42)17-12-27-10-13-28(44-8)14-11-27/h10-15,17,30-33H,16,18-26H2,1-9H3/b17-12+
InChI KeyJDJFVYIDKQYTCC-SFQUDFHCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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 Solubility1.7e-05 g/LALOGPS
logP8.53ALOGPS
logP9.62ChemAxon
logS-7.6ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity184.42 m³·mol⁻¹ChemAxon
Polarizability75.4 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gc0-0415519000-65be53332100bd3fa8f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0500639000-9e7d56cec0c146e19a82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0501911000-bc0e799e47a52db9fef0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-0404901000-191687c1ca750cbe67bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0200419000-225de1423aeb4e1b7f24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0500913000-116b8096d89c3573e2ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-0300900000-497e9dcb3bc5bd20ae5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8c-0107829000-28c2d673db65e5fd0502Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0914110000-428ff7bf3b1bcbdcc3b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fu6-3916210000-cbaeeeb3a446a392f718Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000009000-5497e1df141fc4afd878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-0900024000-bf27a633db6f3048fd7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0800159000-59097bfff52dfd600240Spectrum
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 IDHMDB0033408
FooDB IDFDB011442
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013603
ChEBI IDNot Available
PubChem Compound ID131751417
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