(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-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: 166934
• Molecular Formular: C44H47Cl6NO16
• Molecular Mass: 1058.55908
• Monoisotopic Mass: 1055.10260051
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)[C@@H]([C@@H](N)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: O=C(O[C@H]1C(=O)[C@]2(C)[C@@H](OC(=O)OCC(Cl)(Cl)Cl)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)N)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C)OCC(Cl)(Cl)Cl
• InChI: InChI=1S/C44H47Cl6NO16/c1-21-25(63-36(56)30(53)29(51)23-12-8-6-9-13-23)17-42(59)34(66-35(55)24-14-10-7-11-15-24)32-40(5,33(54)31(28(21)39(42,3)4)65-38(58)62-20-44(48,49)50)26(64-37(57)61-19-43(45,46)47)16-27-41(32,18-60-27)67-22(2)52/h6-15,25-27,29-32,34,53,59H,16-20,51H2,1-5H3/t25-,26-,27+,29-,30+,31+,32-,34-,40+,41-,42+/m0/s1
• InChIKey: WKPUBLILKSBNLE-YXOTWFKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-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)-15-{[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-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: N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel; (αR,βS)-β-Amino-α-hydroxy-benzenepropanoic 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-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

Database IDs

• CAS Number: 114915-16-1
• PubChem SID: 162261067
• PubChem CID: 10996756

CALCULATED PROPERTIES

• Acid pKa: 12.008994
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 4.2633233
• LogD (pH = 7.4): 5.9545774
• Log P: 6.695839
• Molar Refractivity: 240.4879 cm^3
• Polarizability: 96.08208 Å^3
• Polar Surface Area: 242.74 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - D422110

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

REFERENCES

• Ojima, I., et al.: J. Med. Chem., 40, 279 (1997)
• Ojima, I., et al.: Bioorg. Med. Chem., 11, 2867 (1997)
• Liu, C., et al.: Bioorg. Med. Chem., 12, 6147 (1997)