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

• ChemBase ID: 166935
• Molecular Formular: C49H55Cl6NO19
• Molecular Mass: 1174.6743
• Monoisotopic Mass: 1171.14994463
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)[C@@H]([C@@H](NC(=O)OC(CO)(C)C)c1ccccc1)O)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)OCC(Cl)(Cl)Cl)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC(=O)OCC(Cl)(Cl)Cl)C)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: OCC(OC(=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)OCC(Cl)(Cl)Cl)(C)[C@@H](OC(=O)OCC(Cl)(Cl)Cl)C[C@@H]1[C@]3(CO1)OC(=O)C)O)c1ccccc1)(C)C
• InChI: InChI=1S/C49H55Cl6NO19/c1-24-28(70-39(62)33(59)32(26-14-10-8-11-15-26)56-40(63)75-43(3,4)20-57)19-47(66)37(73-38(61)27-16-12-9-13-17-27)35-45(7,36(60)34(31(24)44(47,5)6)72-42(65)69-23-49(53,54)55)29(71-41(64)68-22-48(50,51)52)18-30-46(35,21-67-30)74-25(2)58/h8-17,28-30,32-35,37,57,59,66H,18-23H2,1-7H3,(H,56,63)/t28-,29-,30+,32-,33+,34+,35-,37-,45+,46-,47+/m0/s1
• InChIKey: OEIBKTAURUUWGN-LNJGEEBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-({[(1-hydroxy-2-methylpropan-2-yl)oxy]carbonyl}amino)-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9,12-bis({[(2,2,2-trichloroethoxy)carbonyl]oxy})-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-(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-({[(1-hydroxy-2-methylpropan-2-yl)oxy]carbonyl}amino)-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9,12-bis({[(2,2,2-trichloroethoxy)carbonyl]oxy})-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: [2aR-[2aα,4β,4aβ,6β,9α(αR*,βS*),11α,12α,12aα,12bα]]-α-Hydroxy-β-[[(2-hydroxy-1,1-dimethylethoxy)carbonyl]amino]benzenepropanoic Acid 12b-(Acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; N-Des-t-boc-N-2-(1-hydroxy-2-methyl)propyloxycarbonxyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel

Database IDs

• CAS Number: 160651-89-8
• PubChem SID: 162261068
• PubChem CID: 15765786

CALCULATED PROPERTIES

• Acid pKa: 11.961697
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): 7.141026
• LogD (pH = 7.4): 7.141014
• Log P: 7.141026
• Molar Refractivity: 266.9046 cm^3
• Polarizability: 106.41138 Å^3
• Polar Surface Area: 275.28 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D422225

An intermediate in partial synthesis of major human metabolites of Docetaxel (D494420), an antineoplastic.

REFERENCES

• Commercon, A., et al.: Tetrahedron, 50, 10289 (1994)