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

• ChemBase ID: 161935
• Molecular Formular: C54H57NO15
• Molecular Mass: 960.02808
• Monoisotopic Mass: 959.37282013
• 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)O)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccc(cc1)OCc1ccccc1)NC(=O)c1ccccc1)O)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)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)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C54H57NO15/c1-30-38(68-50(63)43(59)42(55-48(61)35-18-12-8-13-19-35)34-22-24-37(25-23-34)65-28-33-16-10-7-11-17-33)27-54(64)47(69-49(62)36-20-14-9-15-21-36)45-52(6,39(58)26-40-53(45,29-66-40)70-32(3)57)46(60)44(67-31(2)56)41(30)51(54,4)5/h7-25,38-40,42-45,47,58-59,64H,26-29H2,1-6H3,(H,55,61)/t38-,39-,40+,42-,43+,44+,45-,47-,52+,53-,54+/m0/s1
• InChIKey: WJOAVZUMSFWJIU-XZFFVMLHSA-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-[4-(benzyloxy)phenyl]-2-hydroxy-3-(phenylformamido)propanoyl]oxy}-1,9-dihydroxy-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,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-[4-(benzyloxy)phenyl]-2-hydroxy-3-(phenylformamido)propanoyl]oxy}-1,9-dihydroxy-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: 3'-p-O-Benzyl Paclitaxel

Database IDs

• PubChem SID: 162256070
• PubChem CID: 71313922

CALCULATED PROPERTIES

• Acid pKa: 10.364214
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 5.1056356
• LogD (pH = 7.4): 5.1051707
• Log P: 5.105642
• Molar Refractivity: 249.3703 cm^3
• Polarizability: 98.618576 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
• Apperance: White Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B288690

Protected 3’-p-Hydroxy Paclitaxel (H948895), a metabolite of Paclitaxel.

REFERENCES

• Sonnichsen, D., et al.: J. Pharmacol. Exp. Ther., 275, 566 (1995)
• Walle, T., et al.: Drug Metab. Dispos., 23, 506 (1995)
• Torres, K., et al.: Cancer Res., 58, 3620 (1995)
• Svojanovsky, S., et al.: J. Pharm. Biomed. Anal., 20, 549 (1999).