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

• ChemBase ID: 165483
• Molecular Formular: C43H48Cl3NO15
• Molecular Mass: 925.19792
• Monoisotopic Mass: 923.20895288
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)C)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC(=O)OCC(Cl)(Cl)Cl)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)N)O)C
• Canonical SMILES: CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)[C@@H]([C@H](c3ccccc3)N)O)C[C@@](C2(C)C)(O)[C@H]([C@H]2[C@@](C1=O)(C)[C@@H](OC(=O)OCC(Cl)(Cl)Cl)C[C@@H]1[C@]2(CO1)OC(=O)C)OC(=O)c1ccccc1
• InChI: InChI=1S/C43H48Cl3NO15/c1-21-26(59-37(53)31(50)30(47)24-13-9-7-10-14-24)18-42(55)35(61-36(52)25-15-11-8-12-16-25)33-40(6,34(51)32(58-22(2)48)29(21)39(42,4)5)27(60-38(54)57-20-43(44,45)46)17-28-41(33,19-56-28)62-23(3)49/h7-16,26-28,30-33,35,50,55H,17-20,47H2,1-6H3/t26-,27-,28+,30-,31+,32+,33-,35-,40+,41-,42+/m0/s1
• InChIKey: KVRBBGQICGEZIW-GBMYMWMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(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)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-{[(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-Debenzoyl-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]taxol; N-Debenzoyl-7-{[(2,2,2,-trichloroethyl)oxy]carbonyl} Paclitaxel

Database IDs

• CAS Number: 114915-15-0
• PubChem SID: 162259616
• PubChem CID: 10772140

CALCULATED PROPERTIES

• Acid pKa: 11.157876
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 2.068876
• LogD (pH = 7.4): 3.7600658
• Log P: 4.5013914
• Molar Refractivity: 218.9098 cm^3
• Polarizability: 87.75948 Å^3
• Polar Surface Area: 233.51 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - D205125

A Paclitaxel (Taxol) derivative. It can be useful for the treatment of cancer. Antitumor agent.

REFERENCES

• Xiao, X.-Y., et al.: J. Org. Chem., 62, 6029 (1997)