(1S,2S,3R,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-1,8,9-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 171028
• Molecular Formular: C47H51NO15
• Molecular Mass: 869.90554
• Monoisotopic Mass: 869.32586994
• 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@@H]([C@@H]2[C@]1(CO2)OC(=O)C)O)O)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@@H](NC(=O)c1ccccc1)c1ccccc1)O)C
• Canonical SMILES: CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)[C@H](O)[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C47H51NO15/c1-24-30(61-43(57)33(51)32(27-16-10-7-11-17-27)48-41(55)28-18-12-8-13-19-28)22-47(58)40(62-42(56)29-20-14-9-15-21-29)36-45(6,38(54)35(60-25(2)49)31(24)44(47,4)5)37(53)34(52)39-46(36,23-59-39)63-26(3)50/h7-21,30,32-37,39-40,51-53,58H,22-23H2,1-6H3,(H,48,55)/t30-,32-,33+,34-,35+,36-,37-,39+,40-,45-,46+,47+/m0/s1
• InChIKey: NDCWHEDPSFRTDA-FJMWQILYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-1,8,9-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: 6α-hydroxypaclitaxel
• Synonyms: 6α-Hydroxy Taxol; 6α-Hydroxy Paclitaxel

Database IDs

• CAS Number: 153212-75-0
• PubChem SID: 164226938
• PubChem CID: 10056458

CALCULATED PROPERTIES

• Acid pKa: 9.862219
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 2.8485265
• LogD (pH = 7.4): 2.847051
• Log P: 2.8485453
• Molar Refractivity: 219.3916 cm^3
• Polarizability: 87.20104 Å^3
• Polar Surface Area: 241.52 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Methanol
• Apperance: Off-White to Pale Pink Solid
• Melting Point: 177-180°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H948890

The major human metabolite of Paclitaxel.

REFERENCES

• Walle, T., et al.: Biochem. Pharm., 46, 1661 (1993)
• Kumar, G., et al.: Drug Metab. Dispos., 22, 177 (1993)