(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-hexanamido-2-hydroxy-3-phenylpropanoyl]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: 176155
• Molecular Formular: C46H57NO14
• Molecular Mass: 847.94308
• Monoisotopic Mass: 847.37790551
• 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](c1ccccc1)NC(=O)CCCCC)O)C
• Canonical SMILES: CCCCCC(=O)N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@H]3[C@@](C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)(C)[C@@H](O)C[C@@H]1[C@]3(CO1)OC(=O)C)O)c1ccccc1
• InChI: InChI=1S/C46H57NO14/c1-8-9-12-21-33(51)47-35(28-17-13-10-14-18-28)36(52)42(55)59-30-23-46(56)40(60-41(54)29-19-15-11-16-20-29)38-44(7,31(50)22-32-45(38,24-57-32)61-27(4)49)39(53)37(58-26(3)48)34(25(30)2)43(46,5)6/h10-11,13-20,30-32,35-38,40,50,52,56H,8-9,12,21-24H2,1-7H3,(H,47,51)/t30-,31-,32+,35-,36+,37+,38-,40-,44+,45-,46+/m0/s1
• InChIKey: BEHTXUBGUDGCNQ-IEAAAIHOSA-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-hexanamido-2-hydroxy-3-phenylpropanoyl]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-hexanamido-2-hydroxy-3-phenylpropanoyl]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: N-Debenzoyl-N-hexanoylpaclitaxel; (-)-Taxuyunnanine; Taxol C; Taxuyunnanine; Taxuyunnanine A; Paclitaxel C

Database IDs

• CAS Number: 153415-45-3
• PubChem SID: 164232065
• PubChem CID: 9962663

CALCULATED PROPERTIES

• Acid pKa: 10.362904
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.718901
• LogD (pH = 7.4): 3.718435
• Log P: 3.7189074
• Molar Refractivity: 216.0539 cm^3
• Polarizability: 86.38065 Å^3
• Polar Surface Area: 221.29 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P132510

Paclitaxel related compound C. Paclitaxel analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to Paclitaxel.

REFERENCES

• Ojima, I., et al.: J. Med. Chem., 38, 3891 (1995)
• van Asperen, J., et al.: J. Pharm. Sci., 86, 881 (1995)
• Fellner, S., et al.: J. Clin. Invest., 110, 1309 (1995)
• Beckers, T., et al.: Drugs Future, 28, 767 (1995)
• Kemper, E., et al.: Clin. Cancer Res.,