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Record Information
Version2.0
Created at2022-09-11 21:03:41 UTC
Updated at2022-09-11 21:03:41 UTC
NP-MRD IDNP0319824
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s,4s,5r,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-7-(benzoyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-8-yl benzoate
Description(1S,2S,4S,5R,6S,7R,8S,9R,12R)-5,12-bis(acetyloxy)-7-(benzoyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-8-yl benzoate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). (1s,2s,4s,5r,6s,7r,8s,9r,12r)-5,12-bis(acetyloxy)-7-(benzoyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-8-yl benzoate is found in Tripterygium wilfordii. Based on a literature review very few articles have been published on (1S,2S,4S,5R,6S,7R,8S,9R,12R)-5,12-bis(acetyloxy)-7-(benzoyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-8-yl benzoate.
Structure
Thumb
Synonyms
ValueSource
(1S,2S,4S,5R,6S,7R,8S,9R,12R)-5,12-Bis(acetyloxy)-7-(benzoyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0,]dodecan-8-yl benzoic acidGenerator
Chemical FormulaC33H38O11
Average Mass610.6560 Da
Monoisotopic Mass610.24141 Da
IUPAC Name(1S,2S,4S,5R,6S,7R,8S,9R,12R)-5,12-bis(acetyloxy)-7-(benzoyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-8-yl benzoate
Traditional Name(1S,2S,4S,5R,6S,7R,8S,9R,12R)-5,12-bis(acetyloxy)-7-(benzoyloxy)-2,4-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-8-yl benzoate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@@H]1[C@H]2[C@H](OC(=O)C3=CC=CC=C3)[C@H](OC(=O)C3=CC=CC=C3)[C@]3(C)[C@@H](OC(C)=O)[C@@H](O)C[C@](C)(O)[C@@]13OC2(C)C
InChI Identifier
InChI=1S/C33H38O11/c1-18(34)40-25-22(36)17-31(5,39)33-26(41-19(2)35)23(30(3,4)44-33)24(42-28(37)20-13-9-7-10-14-20)27(32(25,33)6)43-29(38)21-15-11-8-12-16-21/h7-16,22-27,36,39H,17H2,1-6H3/t22-,23+,24-,25-,26+,27-,31-,32-,33-/m0/s1
InChI KeyFOIOSVGAFMLLDU-XJQORQGESA-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
Tripterygium wilfordiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentAgarofurans
Alternative Parents
Substituents
  • Agarofuran
  • Tetracarboxylic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Oxepane
  • Cyclitol or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP3.22ChemAxon
pKa (Strongest Acidic)13.52ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area154.89 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity152.61 m³·mol⁻¹ChemAxon
Polarizability61.78 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
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 Compound162926803
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]