[(1S,2S,3R,4S,5S,7S,8S,10R,13S)-5,10-bis(acetyloxy)-1,2,4,7-tetrahydroxy-13-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.03,8]pentadec-11-en-4-yl]methyl benzoate

• ChemBase ID: 176156
• Molecular Formular: C47H53NO15
• Molecular Mass: 871.92142
• Monoisotopic Mass: 871.34152
• 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]([C@@]1(O)COC(=O)c1ccccc1)OC(=O)C)O)C)O)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@H](O)[C@@]2([C@@H]([C@]1(O)COC(=O)c1ccccc1)[C@H](O)[C@]1(O)C[C@@H](C(=C([C@H](C2=O)OC(=O)C)C1(C)C)C)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C
• InChI: InChI=1S/C47H53NO15/c1-25-31(63-43(57)36(52)35(28-16-10-7-11-17-28)48-41(55)29-18-12-8-13-19-29)23-47(59)40(54)38-45(6,39(53)37(62-27(3)50)34(25)44(47,4)5)32(51)22-33(61-26(2)49)46(38,58)24-60-42(56)30-20-14-9-15-21-30/h7-21,31-33,35-38,40,51-52,54,58-59H,22-24H2,1-6H3,(H,48,55)/t31-,32-,33-,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
• InChIKey: BWBMUOOTJLNHSQ-SJBOGKINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,2S,3R,4S,5S,7S,8S,10R,13S)-5,10-bis(acetyloxy)-1,2,4,7-tetrahydroxy-13-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.0^3,^8]pentadec-11-en-4-yl]methyl benzoate
• IUPAC Traditional name: [(1S,2S,3R,4S,5S,7S,8S,10R,13S)-5,10-bis(acetyloxy)-1,2,4,7-tetrahydroxy-13-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.0^3,^8]pentadec-11-en-4-yl]methyl benzoate
• Synonyms: β-(Benzoylamino)-α-hydroxybenzenepropanoic Acid (αR,βS)-(1S,3S,4S,4aR,5S,6S,8S,11R,12aS)-3,11-Bis(acetyloxy)-4-[(benzoyloxy)methyl]-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-1,4,5,6-tetrahydroxy-9,12a,13,13-tetramethyl-12-oxo-6,10-methanobenzocyclodecen-8-yl Ester; Paclitaxel Oxetane Ring-Opened 3-Acetyl 4-Benzoyl Impurity

Database IDs

• CAS Number: 932042-85-8
• PubChem SID: 164232066
• PubChem CID: 71751428

CALCULATED PROPERTIES

• Acid pKa: 9.3196745
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): 2.3770707
• LogD (pH = 7.4): 2.371946
• Log P: 2.3771365
• Molar Refractivity: 221.8046 cm^3
• Polarizability: 87.84619 Å^3
• Polar Surface Area: 252.52 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P132520

An oxetane ring-opened impurity of Paclitaxel (P132500) with no significant activity.

REFERENCES

• Pyo, S.-H. et al.: J. Pharmac. Biomed. Anal., 43, 1141 (2007)