(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-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: 171031
• 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[C@@H]2[C@]1(CO2)OC(=O)C)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@@]4(CO[C@@H]4C[C@@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)C)O)OC(=O)C)O)NC(=O)c1ccccc1
• InChI: InChI=1S/C47H51NO15/c1-24-31(61-43(57)36(53)35(27-17-19-30(51)20-18-27)48-41(55)28-13-9-7-10-14-28)22-47(58)40(62-42(56)29-15-11-8-12-16-29)38-45(6,32(52)21-33-46(38,23-59-33)63-26(3)50)39(54)37(60-25(2)49)34(24)44(47,4)5/h7-20,31-33,35-38,40,51-53,58H,21-23H2,1-6H3,(H,48,55)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
• InChIKey: XKSMHFPSILYEIA-MZXODVADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-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,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-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: 3'-p-Hydroxy Paclitaxel-d5

Database IDs

• PubChem SID: 164226941
• PubChem CID: 71749229

CALCULATED PROPERTIES

• Acid pKa: 9.429232
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 3.2352238
• LogD (pH = 7.4): 3.2312508
• Log P: 3.2352748
• Molar Refractivity: 220.2754 cm^3
• Polarizability: 87.2096 Å^3
• Polar Surface Area: 241.52 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 181-189°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H948897

A labelled metabolite of Paclitaxel; a phase I pharmacokinetic study in patients with solid tumors.

REFERENCES

• Sonnichsen, D., et al.: J. Pharmacol. Exp. Ther., 275, 566 (1995)
• Walle, T., et al.: Drug Metab. Dispos., 23, 506 (1995)
• Torres, K., et al.: Cancer Res., 58, 3620 (1995)
• Svojanovsky, S., et al.: J. Pharm. Biomed. Anal., 20, 549 (1995)