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

• ChemBase ID: 178820
• Molecular Formular: C53H65NO14Si
• Molecular Mass: 968.167
• Monoisotopic Mass: 967.4174323
• 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)O[Si](CC)(CC)CC)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C
• Canonical SMILES: CC[Si](O[C@H]1C[C@H]2OC[C@]2([C@@H]2[C@]1(C)C(=O)[C@H](OC(=O)C)C1=C(C)[C@H](C[C@@]([C@H]2OC(=O)c2ccccc2)(C1(C)C)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)OC(=O)C)(CC)CC
• InChI: InChI=1S/C53H65NO14Si/c1-10-69(11-2,12-3)68-38-28-39-52(30-63-39,67-33(6)56)44-46(66-48(60)36-26-20-15-21-27-36)53(62)29-37(31(4)40(50(53,7)8)43(64-32(5)55)45(58)51(38,44)9)65-49(61)42(57)41(34-22-16-13-17-23-34)54-47(59)35-24-18-14-19-25-35/h13-27,37-39,41-44,46,57,62H,10-12,28-30H2,1-9H3,(H,54,59)/t37-,38-,39+,41-,42+,43+,44-,46-,51+,52-,53+/m0/s1
• InChIKey: LKHIBBPOJARUFY-RGZLSWIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)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)-1-hydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: (αR,βS)-β-(Benzoylamino)-α-hydroxy-benzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(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-[(triethylsilyl)oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; 7-O-(Triethylsilyl)paclitaxel; 7-O-(Triethylsilyl)taxol; 7-O-(Triethylsilyl) Paclitaxel

Database IDs

• CAS Number: 148930-55-6
• PubChem SID: 164234730
• PubChem CID: 11115717

CALCULATED PROPERTIES

• Acid pKa: 11.136176
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): 6.3553987
• LogD (pH = 7.4): 6.3553205
• Log P: 6.3554
• Molar Refractivity: 248.5828 cm^3
• Polarizability: 100.55639 Å^3
• Polar Surface Area: 210.29 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Beige Solid
• Melting Point: 155-159°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T778055

Protected Paclitaxel.

REFERENCES

• Kerns, E., et al.: J. Nat. Products, 57, 1391 (1994)
• Golik, J., et al.: Bioorg. Med. Chem. Lett., 6, 1837 (1994)