(1S,2S,3R,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-1,8,9-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-(4-hydroxyphenyl)-3-[(2H5)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: 167860
• Molecular Formular: C47H51NO16
• Molecular Mass: 885.90494
• Monoisotopic Mass: 885.32078456
• 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](c1ccc(cc1)O)NC(=O)c1ccccc1)O)C
• Canonical SMILES: Oc1ccc(cc1)[C@@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@H]3[C@@](C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)(C)[C@@H](O)[C@@H]([C@@H]1[C@]3(CO1)OC(=O)C)O)O)NC(=O)c1ccccc1
• InChI: InChI=1S/C47H51NO16/c1-23-30(62-43(58)33(52)32(26-17-19-29(51)20-18-26)48-41(56)27-13-9-7-10-14-27)21-47(59)40(63-42(57)28-15-11-8-12-16-28)36-45(6,38(55)35(61-24(2)49)31(23)44(47,4)5)37(54)34(53)39-46(36,22-60-39)64-25(3)50/h7-20,30,32-37,39-40,51-54,59H,21-22H2,1-6H3,(H,48,56)/t30-,32-,33+,34-,35+,36-,37-,39+,40-,45-,46+,47+/m0/s1
• InChIKey: NEGGNAWLXHJUEM-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-(4-hydroxyphenyl)-3-[(^2H₅)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: (1S,2S,3R,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-1,8,9-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-(4-hydroxyphenyl)-3-[(^2H₅)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
• Synonyms: αR,βS)-β-(Benzoylamino-d5)-α,4-dihydroxybenzenepropanoic Acid 6,12b-Bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-3,4,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester; 6α,3'-p-Dihydroxy Paclitaxel-d5

Database IDs

• PubChem SID: 162261993
• PubChem CID: 71316265

CALCULATED PROPERTIES

• Acid pKa: 9.331361
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): 2.5449162
• LogD (pH = 7.4): 2.5399327
• Log P: 2.54498
• Molar Refractivity: 221.3725 cm^3
• Polarizability: 87.872055 Å^3
• Polar Surface Area: 261.75 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 166-170°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D454202

The human liver labelled metabοlite of Paclitaxel. Antitumor agent.

REFERENCES

• Harris, J., et al.: Cancer Res., 54, 4026 (1994)
• Harris, J., et al.: J. Med. Chem., 37, 706 (1994)
• Tolcher, A., et al.: J. Clin. Oncol., 14, 1173 (1994)
• Ohyama, K., et al.: Drug Metab. Dispos., 28, 1303 (1994)