2-(2-Methylbutanoyl)-9-(3-methyl-2E-pentenoyl)-2b,9a-dihydroxy-4Z,10(14)-oplopadien-3-one (CHEM034136)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:41:35 UTC
Update Date2016-11-09 01:21:04 UTC
Accession NumberCHEM034136
Identification
Common Name2-(2-Methylbutanoyl)-9-(3-methyl-2E-pentenoyl)-2b,9a-dihydroxy-4Z,10(14)-oplopadien-3-one
ClassSmall Molecule
Description2-(2-Methylbutanoyl)-9-(3-methyl-2E-pentenoyl)-2b,9a-dihydroxy-4Z,10(14)-oplopadien-3-one is found in tea. 2-(2-Methylbutanoyl)-9-(3-methyl-2E-pentenoyl)-2b,9a-dihydroxy-4Z,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-3-[(2-methylbutanoyl)oxy]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoic acidHMDB
Chemical FormulaC26H38O5
Average Molecular Mass430.577 g/mol
Monoisotopic Mass430.272 g/mol
CAS Registry Number80514-14-3
IUPAC Name(1Z)-1-ethylidene-3-[(2-methylbutanoyl)oxy]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate
Traditional Name(1Z)-1-ethylidene-7-isopropyl-3-[(2-methylbutanoyl)oxy]-4-methylidene-2-oxo-hexahydroinden-5-yl (2E)-3-methylpent-2-enoate
SMILESCCC(C)C(=O)OC1C2C(C(CC(OC(=O)\C=C(/C)CC)C2=C)C(C)C)\C(=C\C)C1=O
InChI IdentifierInChI=1S/C26H38O5/c1-9-15(6)12-21(27)30-20-13-19(14(4)5)23-18(11-3)24(28)25(22(23)17(20)8)31-26(29)16(7)10-2/h11-12,14,16,19-20,22-23,25H,8-10,13H2,1-7H3/b15-12+,18-11-
InChI KeyXTQQLVJPORCMAK-XIMUYODMSA-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
  • Alpha-acyloxy ketone
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • 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 Solubility0.00075 g/LALOGPS
logP5.14ALOGPS
logP6.45ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)17.58ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity122.46 m³·mol⁻¹ChemAxon
Polarizability48.82 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0670-9024100000-809c23c20b0e21f70676Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00m1-9018800000-bcc75794e1f8b95e6decSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-9002100000-8e130dfdb103749d5c8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9020000000-0d3ee8d88872d521d8d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2305900000-22ae90215b8546f72bc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-7439300000-1ecf519c53355ec81b23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxs-9461000000-aeaec6c167d419c9310eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0092-9400200000-92e4f083ee3c7a64ad22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-015a-9230100000-051a91b97c27b85f2e00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-7191100000-a9853d2ac945e6b8b4c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0091000000-afb8fd51223b6814a043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015i-0091000000-ad4c09beef814fc62db7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9160000000-eadad639e5bb29d0653aSpectrum
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 IDHMDB0040994
FooDB IDFDB020854
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015068
ChEBI ID175489
PubChem Compound ID131753007
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