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Record Information
Version2.0
Created at2022-09-12 14:37:48 UTC
Updated at2022-09-12 14:37:48 UTC
NP-MRD IDNP0329840
Secondary Accession NumbersNone
Natural Product Identification
Common Name9,10,13-tris(acetyloxy)-2,7-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-5-yl 3-phenylprop-2-enoate
Description9,10,13-Tris(acetyloxy)-2,7-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]Pentadeca-3,8,11-trien-5-yl 3-phenylprop-2-enoate belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. 9,10,13-tris(acetyloxy)-2,7-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-5-yl 3-phenylprop-2-enoate is found in Taxus wallichiana. 9,10,13-Tris(acetyloxy)-2,7-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]Pentadeca-3,8,11-trien-5-yl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
9,10,13-Tris(acetyloxy)-2,7-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-5-yl 3-phenylprop-2-enoic acidGenerator
Chemical FormulaC35H44O11
Average Mass640.7260 Da
Monoisotopic Mass640.28836 Da
IUPAC Name9,10,13-tris(acetyloxy)-2,7-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-5-yl 3-phenylprop-2-enoate
Traditional Name9,10,13-tris(acetyloxy)-2,7-dihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethylbicyclo[9.3.1]pentadeca-3,8,11-trien-5-yl 3-phenylprop-2-enoate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1CC2C(O)C=C(CO)C(CC(O)C(C)=C(OC(C)=O)C(OC(C)=O)C(=C1C)C2(C)C)OC(=O)C=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C35H44O11/c1-19-27(40)17-30(46-31(42)14-13-24-11-9-8-10-12-24)25(18-36)15-28(41)26-16-29(43-21(3)37)20(2)32(35(26,6)7)34(45-23(5)39)33(19)44-22(4)38/h8-15,26-30,34,36,40-41H,16-18H2,1-7H3
InChI KeyQLIOXOVTRYEVGV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Taxus wallichianaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentTaxanes and derivatives
Alternative Parents
Substituents
  • 3,8-seco-taxane diterpenoid
  • Tetracarboxylic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Enol ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.78ALOGPS
logP1.96ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area165.89 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity170.05 m³·mol⁻¹ChemAxon
Polarizability67.24 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74956029
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]