(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-(acetyloxy)-1,9,12-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 168036
• Molecular Formular: C45H49NO13
• Molecular Mass: 811.86946
• Monoisotopic Mass: 811.32039063
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2O)([C@@H](C[C@@H]2[C@]1(CO2)OC(=O)C)O)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C
• Canonical SMILES: CC(=O)O[C@@]12CO[C@@H]1C[C@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H]([C@H](c3ccccc3)NC(=O)c3ccccc3)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
• InChI: InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30+,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
• InChIKey: TYLVGQKNNUHXIP-DIYBZAJCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-(acetyloxy)-1,9,12-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: (1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-(acetyloxy)-1,9,12-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: 10-Deacetyl-7-epi-taxol; 10-Deacetyl-7-epitaxol; 10-Desacetyl-7-epipaclitaxel; 7-Epi-10-deacetyltaxol; Ormosin VI; 7-Epi 10-Desacetyl Paclitaxel

Database IDs

• CAS Number: 78454-17-8
• PubChem SID: 162262168
• PubChem CID: 14355298

CALCULATED PROPERTIES

• Acid pKa: 10.958207
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 3.097713
• LogD (pH = 7.4): 3.0975947
• Log P: 3.0977147
• Molar Refractivity: 209.143 cm^3
• Polarizability: 82.69364 Å^3
• Polar Surface Area: 215.22 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Ethyl acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 163-170°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E583500

Paclitaxel impurity. Paclitaxel related compound B. The compound has been isolated from Taxus yunnanensis. It has shown to have potential growth inhibitory activities against human cancer cells.

REFERENCES

• Schiff, P., et al.: Nature, 277, 665 (1979)
• Parness, J., et al.: J. Cell Biol., 91, 479 (1979)
• Swindell, C., et al.: J. Med. Chem., 34, 1176 (1979)
• Dordunoo, S., et al.: Int. J. Pharm., 133, 191 (1979)
• Ueda, J., et al.: Planta Med. Epub (1979)