(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1,12-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(2R,3R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 165458
• Molecular Formular: C50H57NO17
• Molecular Mass: 943.98408
• Monoisotopic Mass: 943.36264937
• SMILES: C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2O)([C@H](C[C@@H]2[C@]1(CO2)OC(=O)C)O[C@H]1OC[C@@H](C([C@@H]1O)O)O)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C
• Canonical SMILES: CC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H]([C@H](c3ccccc3)NC(=O)c3ccccc3)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O[C@H]1OC[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C50H57NO17/c1-25-31(65-45(61)38(56)35(27-15-9-6-10-16-27)51-43(59)28-17-11-7-12-18-28)22-50(62)42(67-44(60)29-19-13-8-14-20-29)40-48(5,41(58)37(55)34(25)47(50,3)4)32(21-33-49(40,24-64-33)68-26(2)52)66-46-39(57)36(54)30(53)23-63-46/h6-20,30-33,35-40,42,46,53-57,62H,21-24H2,1-5H3,(H,51,59)/t30-,31-,32-,33+,35-,36?,37+,38+,39+,40-,42-,46+,48+,49-,50+/m0/s1
• InChIKey: ORKLEZFXASNLFJ-ADAUMUDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-1,12-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(2R,3R,5S)-3,4,5-trihydroxyoxan-2-yl]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)-1,12-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-9-{[(2R,3R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: 10-Deacetyl-7-xylosyltaxol; 10-Deacetylpaclitaxel 7-Xyloside; 10-Deacetyltaxol 7-Xyloside; 7-Xylosyl-10-deacetyltaxol; 7β-Xylosyl-10-deacetyltaxol; 10-Deacetyl-7-xylosyl Paclitaxel

Database IDs

• CAS Number: 90332-63-1
• PubChem SID: 162259591
• PubChem CID: 71315214

CALCULATED PROPERTIES

• Acid pKa: 11.487853
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): 1.9572134
• LogD (pH = 7.4): 1.9571785
• Log P: 1.9572139
• Molar Refractivity: 235.5938 cm^3
• Polarizability: 93.91171 Å^3
• Polar Surface Area: 274.14 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D198965

A metabolite of Paclitaxel (P132500).

REFERENCES

• Li, S., et al.: J. Pharm. Biomed. Anal., 49, 81, (2008)
• Gut, I., et al.: Xenobiotica, 36, 772 ( 2006), Zhang, J., et al.: Drug Metab. Dispos., 36, 418 (2008)