(1S,2S,3R,4S,7R,9R,10S,12S,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 163519
• Molecular Formular: C45H57NO14
• Molecular Mass: 835.93238
• Monoisotopic Mass: 835.37790551
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)[C@@H]([C@@H](NC(=O)OC(C)(C)C)c1ccccc1)O)([C@H]([C@H]1[C@](C(=O)[C@H]2OC)([C@@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC)C)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: CO[C@@H]1C(=O)[C@]2(C)[C@H](OC)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)OC(C)(C)C)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29+,30+,32-,33+,34-,35-,37-,43+,44-,45+/m0/s1
• InChIKey: BMQGVNUXMIRLCK-VGSBGYIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9R,10S,12S,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-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,9R,10S,12S,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-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: (αR,βS)-β-[[(1,1-Dimethylethoxy)carbonyl]amino]-α-hydroxybenzenepropanoic Acid (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-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; TXD 258; XRP 6258; β-[[(1,1-Dimethylethoxy)carbonyl]amino]-α-hydroxybenzenepropanoic Acid [2aR-[2aα,4β,4aβ,6β,9α(αR*,βS*),11α,12α,12aα,12bα]]-12b-(Acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; Cabazitaxel

Database IDs

• CAS Number: 183133-96-2
• PubChem SID: 162257654
• PubChem CID: 71314469

CALCULATED PROPERTIES

• Acid pKa: 11.967099
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): 4.203044
• LogD (pH = 7.4): 4.2030325
• Log P: 4.203044
• Molar Refractivity: 213.4041 cm^3
• Polarizability: 85.22958 Å^3
• Polar Surface Area: 202.45 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 181-183°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C046500

A novel semi-synthetic taxane with antitumor activity used for the treatment of castration-resistant prostate cancer. A microtubule inhibitor.

REFERENCES

• Agarwal, N. et al.: Fut. Oncol., 7, 15 (2011)
• Mita, A. et al.: Clin. Cancer Res., 15, 723 (2011)
• Figg, W.D. et al.: Cancer Biol. Ther., 10, 1233 (2011)