(1S,2S,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-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: 72544
• Molecular Formular: C43H53NO14
• Molecular Mass: 807.87922
• Monoisotopic Mass: 807.34660538
• SMILES: c1ccccc1C(=O)O[C@H]1C2[C@]3([C@@H](C[C@@H]([C@@]2(C)C(=O)[C@H](O)C2=C([C@H](C[C@@]1(C2(C)C)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)OC(C)(C)C)O)C)O)OC3)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1(C2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H]([C@H](c3ccccc3)NC(=O)OC(C)(C)C)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
• InChI: InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33?,35-,41+,42-,43+/m0/s1
• InChIKey: ZDZOTLJHXYCWBA-JXHJHTFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-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; (1S,2S,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: (1S,2S,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-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; (1S,2S,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
• Synonyms: Taxotere; Docetaxel

Database IDs

• CAS Number: 114977-28-5
• PubChem SID: 162037469
• PubChem CID: 9877265

CALCULATED PROPERTIES

• Acid pKa: 10.957364
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 2.9167895
• LogD (pH = 7.4): 2.9166708
• Log P: 2.916791
• Molar Refractivity: 203.9017 cm^3
• Polarizability: 81.427376 Å^3
• Polar Surface Area: 224.45 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: Microtubule Formation

Product Information

• Salt Data: Free Base
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S1148

Research Area: Solid tumours
Biological Activity:
Docetaxel (Taxotere) is a semi-synthetic, second-generation taxane, with anti-neoplastic application for the treatment of breast, ovarian, and non-small cell lung cancer. [1]Docetaxel binds to and stabilizes tubulin, thereby inhibiting microtubule disassembly which results in cell- cycle arrest at the G2/M phase and cell death. The overall cells mean IC50 for docetaxel treatment was 4.67 nM，similar to IC50 values observed across the NCI60 panel of human tumor cell lines, which exhibit a mean docetaxel IC50 of 23.4 nM, with a range of 0.31–100 nM. [2]This agent also inhibits pro-angiogenic factors such as VEGF and displays immunomodulatory and pro-inflammatory properties by inducing various mediators of the inflammatory response. Docetaxel has been studied for use as a radiation-sensitizing agent. [3] 

REFERENCES

• James W. Watters et al. PNAS.2004 August 10;101(32):11809-11814