(1S,2S,3R,4S,7S,9R,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-8,11-dioxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 176007
• Molecular Formular: C43H51NO15
• Molecular Mass: 821.86274
• Monoisotopic Mass: 821.32586994
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)[C@@H]([C@@H](NC(=O)OC(C)(C)C)c1ccccc1)O)([C@H]([C@H]1[C@](C(=O)[C@@H]2O)([C@H](C(=O)[C@@H]2[C@]1(CO2)OC(=O)C)O)C)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: CC(=O)O[C@@]12CO[C@@H]1C(=O)[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)OC(C)(C)C)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
• InChI: InChI=1S/C43H51NO15/c1-21-25(56-37(52)29(47)27(23-15-11-9-12-16-23)44-38(53)59-39(3,4)5)19-43(54)35(57-36(51)24-17-13-10-14-18-24)31-41(8,32(49)28(46)26(21)40(43,6)7)33(50)30(48)34-42(31,20-55-34)58-22(2)45/h9-18,25,27-29,31,33-35,46-47,50,54H,19-20H2,1-8H3,(H,44,53)/t25-,27-,28+,29+,31-,33-,34+,35-,41+,42+,43+/m0/s1
• InChIKey: FNNBOGRAQOBUFT-JHNGNYFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7S,9R,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-8,11-dioxo-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,7S,9R,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-8,11-dioxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: 6-Oxo Docetaxel

Database IDs

• PubChem SID: 164231917
• PubChem CID: 71751373

CALCULATED PROPERTIES

• Acid pKa: 11.046398
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 2.8416712
• LogD (pH = 7.4): 2.8415744
• Log P: 2.8416724
• Molar Refractivity: 204.2321 cm^3
• Polarizability: 81.55105 Å^3
• Polar Surface Area: 241.52 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O855780

Docetaxel impurity. Taxol derivatives are useful for the same cancers for which Taxol (Paclitaxel-P132500) has been shown active, including human ovarian cancer, breast cancer, and malignant melanoma as well as lung cancer, gastric cancer, colon cancer, h