(1R,3R,4R,5S,6S,8x)-1-Acetoxy-8-angeloyloxy-3,4-epoxy-5-hydroxy-7(14),10-bisaboladien-2-one (CHEM033269)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:02:47 UTC
Update Date2016-11-09 01:20:53 UTC
Accession NumberCHEM033269
Identification
Common Name(1R,3R,4R,5S,6S,8x)-1-Acetoxy-8-angeloyloxy-3,4-epoxy-5-hydroxy-7(14),10-bisaboladien-2-one
ClassSmall Molecule
Description(1R,3R,4R,5S,6S,8x)-1-Acetoxy-8-angeloyloxy-3,4-epoxy-5-hydroxy-7(14),10-bisaboladien-2-one is found in tea. (1R,3R,4R,5S,6S,8x)-1-Acetoxy-8-angeloyloxy-3,4-epoxy-5-hydroxy-7(14),10-bisaboladien-2-one is a constituent of flower buds of Tussilago farfara (coltsfoot).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
UlithiacyclamideHMDB
2-[4-(Acetyloxy)-2-hydroxy-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-6-methylhepta-1,5-dien-3-yl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC22H30O7
Average Molecular Mass406.469 g/mol
Monoisotopic Mass406.199 g/mol
CAS Registry Number348113-03-1
IUPAC Name2-[4-(acetyloxy)-2-hydroxy-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-[4-(acetyloxy)-2-hydroxy-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(O)C2OC2(C)C(=O)C1OC(C)=O
InChI IdentifierInChI=1S/C22H30O7/c1-8-12(4)21(26)28-15(10-9-11(2)3)13(5)16-17(24)20-22(7,29-20)19(25)18(16)27-14(6)23/h8-9,15-18,20,24H,5,10H2,1-4,6-7H3/b12-8-
InChI KeyNTVBUJOKRXFMAK-WQLSENKSSA-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
  • Fatty acid ester
  • Oxepane
  • Alpha-acyloxy ketone
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxirane
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • 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 Solubility0.15 g/LALOGPS
logP2.55ALOGPS
logP3.06ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.06ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area102.43 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.76 m³·mol⁻¹ChemAxon
Polarizability42.2 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, Positivesplash10-0a4i-9123000000-3a83847a45edb0df5166Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9202100000-b427b90aebebb79d9b80Spectrum
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, Positivesplash10-0a4i-3019300000-651f6e4aa4a2ec78afbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9134000000-f52f5096d8ac277c7343Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9010000000-1e4531c74a03f0e6e1bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-5019700000-29ae9d439f6961049f1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-8129100000-d574eca8aa43271668f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9122000000-fc20b0fcf809f9e4c58dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-9011300000-a5921d1efa8c5eea0664Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-9023100000-87b9475cd2a30ca5d327Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9100000000-3db0d1afcd0f93bb665aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0094100000-35a7052abd7884eb1f1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0195300000-67162f72585713b9a472Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9431000000-c0f1bd1873242ac798c0Spectrum
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 IDHMDB0039971
FooDB IDFDB019639
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014909
ChEBI ID171847
PubChem Compound ID131752774
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