(1S,2S,3R,4S,7R,11S,13R,16S)-4-(acetyloxy)-16-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,13-dihydroxy-11,15,18,18-tetramethyl-12-oxo-6,9-dioxapentacyclo[12.3.1.03,11.04,7.08,10]octadec-14-en-2-yl benzoate

• ChemBase ID: 168111
• Molecular Formular: C43H51NO14
• Molecular Mass: 805.86334
• Monoisotopic Mass: 805.33095532
• 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)(C2C([C@@H]3[C@]1(CO3)OC(=O)C)O2)C)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: O=C(OC(C)(C)C)N[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]4C4C([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)O)C)O4)OC(=O)C)O)c1ccccc1
• InChI: InChI=1S/C43H51NO14/c1-21-25(54-37(50)29(47)27(23-15-11-9-12-16-23)44-38(51)58-39(3,4)5)19-43(52)35(56-36(49)24-17-13-10-14-18-24)31-41(8,32(48)28(46)26(21)40(43,6)7)33-30(55-33)34-42(31,20-53-34)57-22(2)45/h9-18,25,27-31,33-35,46-47,52H,19-20H2,1-8H3,(H,44,51)/t25-,27-,28+,29+,30?,31-,33?,34+,35-,41+,42+,43+/m0/s1
• InChIKey: YIMIGTNUBJPFFC-HVTKTNJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,11S,13R,16S)-4-(acetyloxy)-16-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,13-dihydroxy-11,15,18,18-tetramethyl-12-oxo-6,9-dioxapentacyclo[12.3.1.0^3,^1^1.0^4,^7.0^8,^1^0]octadec-14-en-2-yl benzoate
• IUPAC Traditional name: (1S,2S,3R,4S,7R,11S,13R,16S)-4-(acetyloxy)-16-{[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy}-1,13-dihydroxy-11,15,18,18-tetramethyl-12-oxo-6,9-dioxapentacyclo[12.3.1.0^3,^1^1.0^4,^7.0^8,^1^0]octadec-14-en-2-yl benzoate
• Synonyms: β-[[(1,1-Dimethylethoxy)carbonyl]amino]-α-hydroxybenzenepropanoic Acid; 3a-(Acetyloxy)-4-(benzoyloxy)-1a,1b,3a,3b,4,5,6,7,10,11,11a,11b-dodecahydro-5,10-dihydroxy-8,11a,12,12-tetramethyl-11-oxo-5,9-methano-3H-cyclodec[3,4]oxireno[5,6]benz[1,2-b]oxet-7-yl Ester; 6,7-Epoxy Docetaxel(Mixture of Diastereomers)

Database IDs

• CAS Number: 181208-36-6
• PubChem SID: 162262243
• PubChem CID: 71316372

CALCULATED PROPERTIES

• Acid pKa: 11.548852
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.3881996
• LogD (pH = 7.4): 3.388169
• Log P: 3.3881998
• Molar Refractivity: 201.4887 cm^3
• Polarizability: 80.78282 Å^3
• Polar Surface Area: 216.75 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E589190

A taxane derivative modified at 6 and 7 positions for use as antitumor agent.

REFERENCES

• Gaskin, F., et al.: J. Mol. Biol., 89, 737 (1974)
• Mathew, A.E., et al.: J. Med. Chem., 35, 145 (1974)