(1S,3S,4S,5R,6x,8x)-1,5-Diacetoxy-8-angeloyloxy-3,4-epoxy-7(14),10-bisaboladien-2-one (CHEM028608)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:34:18 UTC
Update Date2016-11-09 01:18:43 UTC
Accession NumberCHEM028608
Identification
Common Name(1S,3S,4S,5R,6x,8x)-1,5-Diacetoxy-8-angeloyloxy-3,4-epoxy-7(14),10-bisaboladien-2-one
ClassSmall Molecule
Description(1S,3S,4S,5R,6x,8x)-1,5-Diacetoxy-8-angeloyloxy-3,4-epoxy-7(14),10-bisaboladien-2-one is found in tea. (1S,3S,4S,5R,6x,8x)-1,5-Diacetoxy-8-angeloyloxy-3,4-epoxy-7(14),10-bisaboladien-2-one is a constituent of Tussilago farfara (coltsfoot)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-[2,4-Bis(acetyloxy)-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-6-methylhepta-1,5-dien-3-yl (2Z)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC24H32O8
Average Molecular Mass448.506 g/mol
Monoisotopic Mass448.210 g/mol
CAS Registry Number246024-91-9
IUPAC Name2-[2,4-bis(acetyloxy)-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-6-methylhepta-1,5-dien-3-yl (2Z)-2-methylbut-2-enoate
Traditional Name2-[2,4-bis(acetyloxy)-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-6-methylhepta-1,5-dien-3-yl (2Z)-2-methylbut-2-enoate
SMILESC\C=C(\C)C(=O)OC(CC=C(C)C)C(=C)C1C(OC(C)=O)C2OC2(C)C(=O)C1OC(C)=O
InChI IdentifierInChI=1S/C24H32O8/c1-9-13(4)23(28)31-17(11-10-12(2)3)14(5)18-19(29-15(6)25)21(27)24(8)22(32-24)20(18)30-16(7)26/h9-10,17-20,22H,5,11H2,1-4,6-8H3/b13-9-
InChI KeyZCWNIRCWJUACBO-LCYFTJDESA-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
  • Bisabolane sesquiterpenoid
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Oxepane
  • Alpha-acyloxy ketone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Ketone
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Dialkyl ether
  • Oxirane
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.0091 g/LALOGPS
logP2.88ALOGPS
logP3.51ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.06ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area108.5 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity115.91 m³·mol⁻¹ChemAxon
Polarizability47.05 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-9204000000-941a179e5bdbdb4b8c7bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053b-3016900000-88d60a046177efd356bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9146300000-e72434362a25faf43bc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9012000000-ade5dbf44869a13bf351Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-3002900000-2c846ba89ecdb7615adaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9138700000-8b683a8e079ab9e7a655Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9015000000-7974a19df6993a52b606Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4s-0059100000-39df04f8521ae1120671Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-0049200000-71ba244ff03d5c3ddad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9162000000-151a804d9181b3c0deb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9012500000-60d704f5bcf08c203e98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9007200000-911c1e64151505113b3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9200000000-0d17697baf3c566ccaadSpectrum
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 IDHMDB0034584
FooDB IDFDB013100
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013742
ChEBI ID175590
PubChem Compound ID131751586
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