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

• ChemBase ID: 165484
• Molecular Formular: C50H54Cl3NO16
• Molecular Mass: 1031.31986
• Monoisotopic Mass: 1029.25081769
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)C)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC(=O)OCC(Cl)(Cl)Cl)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccc(cc1)OCc1ccccc1)N)O)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](OC(=O)OCC(Cl)(Cl)Cl)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccc(cc1)OCc1ccccc1)N)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C50H54Cl3NO16/c1-26-33(67-44(60)38(57)37(54)30-17-19-32(20-18-30)63-23-29-13-9-7-10-14-29)22-49(62)42(69-43(59)31-15-11-8-12-16-31)40-47(6,41(58)39(66-27(2)55)36(26)46(49,4)5)34(68-45(61)65-25-50(51,52)53)21-35-48(40,24-64-35)70-28(3)56/h7-20,33-35,37-40,42,57,62H,21-25,54H2,1-6H3/t33-,34-,35+,37-,38+,39+,40-,42-,47+,48-,49+/m0/s1
• InChIKey: JPRBHQJDMQCLPG-XOVTVWCYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-amino-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-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,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-amino-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(2,2,2-trichloroethoxy)carbonyl]oxy}-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: N-Debenzoyl-3'-p-O-benzy-7-{[(2,2,2,-trichloroethyl)oxy]carbonyl} Paclitaxel

Database IDs

• PubChem SID: 162259617
• PubChem CID: 71315231

CALCULATED PROPERTIES

• Acid pKa: 11.159717
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 3.644368
• LogD (pH = 7.4): 5.336302
• Log P: 6.0681934
• Molar Refractivity: 249.9856 cm^3
• Polarizability: 99.79563 Å^3
• Polar Surface Area: 242.74 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-white Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D205135

A protected Paclitaxel (Taxol) derivative. It can be useful for the treatment of cancer. Antitumor agent.

REFERENCES

• Xiao, X.-Y., et al.: J. Org. Chem., 62, 6029 (1997)