(1S,2S,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-2-[(tert-butyldimethylsilyl)oxy]-3-phenyl-3-(phenylformamido)propanoyl]oxy}-1,8,9-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 163346
• Molecular Formular: C53H65NO15Si
• Molecular Mass: 984.1664
• Monoisotopic Mass: 983.41234692
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H](C1[C@](C(=O)[C@@H]2OC(=O)C)([C@H]([C@@H]([C@@H]2[C@]1(CO2)OC(=O)C)O)O)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O[Si](C(C)(C)C)(C)C)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)[C@H](O)[C@@H]3[C@](C2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O[Si](C(C)(C)C)(C)C)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C53H65NO15Si/c1-29-35(66-48(62)40(69-70(10,11)49(4,5)6)37(32-21-15-12-16-22-32)54-46(60)33-23-17-13-18-24-33)27-53(63)45(67-47(61)34-25-19-14-20-26-34)41-51(9,43(59)39(65-30(2)55)36(29)50(53,7)8)42(58)38(57)44-52(41,28-64-44)68-31(3)56/h12-26,35,37-42,44-45,57-58,63H,27-28H2,1-11H3,(H,54,60)/t35-,37-,38-,39+,40+,41?,42-,44+,45-,51-,52+,53+/m0/s1
• InChIKey: ACJHNDYFTFXEOF-ADQLVGGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-2-[(tert-butyldimethylsilyl)oxy]-3-phenyl-3-(phenylformamido)propanoyl]oxy}-1,8,9-trihydroxy-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,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-2-[(tert-butyldimethylsilyl)oxy]-3-phenyl-3-(phenylformamido)propanoyl]oxy}-1,8,9-trihydroxy-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: 2'-O-(tert-Butyldimethylsilyl)-6α-hydroxy Paclitaxel

Database IDs

• CAS Number: 211732-86-4
• PubChem SID: 162257481
• PubChem CID: 46780939

CALCULATED PROPERTIES

• Acid pKa: 9.865337
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 5.4370813
• LogD (pH = 7.4): 5.4356165
• Log P: 5.4371
• Molar Refractivity: 249.2397 cm^3
• Polarizability: 101.20666 Å^3
• Polar Surface Area: 230.52 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B691300

6α-Hydroxypaclitaxel derivative.

REFERENCES

• Monsarrat, B., et al.: Drug Metab. Dispos., 18, 895 (1990)
• Walle, T., et al.: Biochem. Pharm., 46, 1661 (1990)
• Harris, J., et al.: J. Med. Chem., 37, 706 (1990)