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

• ChemBase ID: 176008
• Molecular Formular: C43H51NO14
• Molecular Mass: 805.86334
• Monoisotopic Mass: 805.33095532
• 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)C2=O)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)O)C)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[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(=O)C1=O)C)C)O
• InChI: InChI=1S/C43H51NO14/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/h9-18,26-28,30,32-33,35,46,48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,32+,33-,35-,41+,42-,43+/m0/s1
• InChIKey: ZOLQDWANVNOXBK-YYCGEXIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9-dihydroxy-10,14,17,17-tetramethyl-11,12-dioxo-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,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1,9-dihydroxy-10,14,17,17-tetramethyl-11,12-dioxo-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,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5,6-dioxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; 10-Oxo Docetaxel

Database IDs

• CAS Number: 167074-97-7
• PubChem SID: 164231918
• PubChem CID: 15200439

CALCULATED PROPERTIES

• Acid pKa: 11.965227
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.9885347
• LogD (pH = 7.4): 3.988523
• Log P: 3.9885347
• Molar Refractivity: 203.3603 cm^3
• Polarizability: 80.88712 Å^3
• Polar Surface Area: 221.29 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 135-143°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - O855800

A novel taxoid having remarkable anti-tumor properties. Docetaxel (D494420) intermediate.

REFERENCES

• Appendino, G., et al.: Tetrahedron Lett., 37, 7836 (1996)