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

• ChemBase ID: 162429
• Molecular Formular: C57H77NO13Si2
• Molecular Mass: 1040.39118
• Monoisotopic Mass: 1039.49334459
• 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[Si](CC)(CC)CC)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O[Si](CC)(CC)CC)C
• Canonical SMILES: CC[Si](O[C@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@@]4(CO[C@@H]4C[C@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)O)C)O[Si](CC)(CC)CC)OC(=O)C)(CC)CC
• InChI: InChI=1S/C57H77NO13Si2/c1-12-72(13-2,14-3)70-42-33-43-56(35-66-43,69-37(8)59)48-50(68-52(63)40-31-25-20-26-32-40)57(65)34-41(36(7)44(54(57,9)10)46(60)49(61)55(42,48)11)67-53(64)47(71-73(15-4,16-5)17-6)45(38-27-21-18-22-28-38)58-51(62)39-29-23-19-24-30-39/h18-32,41-43,45-48,50,60,65H,12-17,33-35H2,1-11H3,(H,58,62)/t41-,42+,43+,45-,46+,47+,48-,50-,55+,56-,57+/m0/s1
• InChIKey: XEYAPYLENSHPRC-VZECWUOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9R,10S,12R,15S)-4-(acetyloxy)-1,12-dihydroxy-10,14,17,17-tetramethyl-11-oxo-15-{[(2R,3S)-3-phenyl-3-(phenylformamido)-2-[(triethylsilyl)oxy]propanoyl]oxy}-9-[(triethylsilyl)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,9R,10S,12R,15S)-4-(acetyloxy)-1,12-dihydroxy-10,14,17,17-tetramethyl-11-oxo-15-{[(2R,3S)-3-phenyl-3-(phenylformamido)-2-[(triethylsilyl)oxy]propanoyl]oxy}-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: (αR,βS)-(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-6,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[(triethylsilyl)oxy]-benzenepropanoic Acid β-(Benzoylamino)-α-[(triethylsilyl)oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; 2',7-Bis-O-(Triethylsilyl) 10-Desacetyl Paclitaxel

Database IDs

• CAS Number: 155556-72-2
• PubChem SID: 162256564
• PubChem CID: 71314113

CALCULATED PROPERTIES

• Acid pKa: 11.771782
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): 8.9835
• LogD (pH = 7.4): 8.983481
• Log P: 8.9835
• Molar Refractivity: 269.7196 cm^3
• Polarizability: 110.73998 Å^3
• Polar Surface Area: 193.22 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B585470

Protected Paclitaxel (P132500). An antineoplastic. Used in the study of structure and function of microtubles into tubulin. Paclitaxel is now used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanced forms of Kaposi's sa

REFERENCES

• Letourneau, P.C., et al.: J. Cell Biol., 98, 1355 (1984)
• Manfredi, J.J., et al.: Pharmacol. Ther., 25, 83 (1984)
• Danesi, R., et al.: Mol. Pharmacol., 47, 1106 (1984)
• Markman, M., et al.: Expert. Opin. Pharmacother., 3, 755 (1984)
• Stone, G.W., et al.: