(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl (2H5)benzoate

• ChemBase ID: 176154
• Molecular Formular: C47H51NO14
• Molecular Mass: 853.90614
• Monoisotopic Mass: 853.33095532
• 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)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](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
• InChIKey: RCINICONZNJXQF-MZXODVADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl (^2H₅)benzoate
• IUPAC Traditional name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl (^2H₅)benzoate
• Synonyms: Abraxane-d5; Genaxol-d5; Genetaxyl-d5; OncoGel-d5; Onxal-d5; Pacliex-d5; (-)-Paclitaxel-d5; Taxol-d5; Yewtaxan-d5; NSC 125973-d5; Paclitaxel-d5 (Benzoyloxy)

Database IDs

• CAS Number: 1261254-56-1
• PubChem SID: 164232064
• PubChem CID: 71751427

CALCULATED PROPERTIES

• Acid pKa: 10.363949
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.5388339
• LogD (pH = 7.4): 3.5383687
• Log P: 3.53884
• Molar Refractivity: 218.2945 cm^3
• Polarizability: 86.56818 Å^3
• Polar Surface Area: 221.29 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P132503

Labelled Paclitaxel (P132500). An antineoplastic. Used in the study of structure and function of microtubles into tubulin.

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.: