(1S,2S,3R,4S,7R,9S,10S,12R)-4-(acetyloxy)-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 176003
• Molecular Formular: C29H34O10
• Molecular Mass: 542.57426
• Monoisotopic Mass: 542.21519729
• SMILES: C1(=C2C([C@@](CC1=O)([C@H]([C@H]1[C@](C(=O)[C@@H]2O)([C@H](C[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[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)CC(=O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
• InChI: InChI=1S/C29H34O10/c1-14-17(31)12-29(36)24(38-25(35)16-9-7-6-8-10-16)22-27(5,23(34)21(33)20(14)26(29,3)4)18(32)11-19-28(22,13-37-19)39-15(2)30/h6-10,18-19,21-22,24,32-33,36H,11-13H2,1-5H3/t18-,19+,21+,22-,24-,27+,28-,29+/m0/s1
• InChIKey: WMZBAMYUOYXRSF-RIFKXWPOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9S,10S,12R)-4-(acetyloxy)-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11,15-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,7R,9S,10S,12R)-4-(acetyloxy)-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-2a,4,4a,10,11,12,12a,12b-octahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxete-5,9(3H,6H)-dione; 10-Deacetyl-13-oxobaccatin III; 13-Oxo-10-deacetyl Baccatin III

Database IDs

• CAS Number: 92950-42-0
• PubChem SID: 164231913
• PubChem CID: 15227070

CALCULATED PROPERTIES

• Acid pKa: 9.433427
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.3937821
• LogD (pH = 7.4): 1.3898329
• Log P: 1.3938327
• Molar Refractivity: 135.2644 cm^3
• Polarizability: 53.867138 Å^3
• Polar Surface Area: 156.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O850110

13-Oxo-10-deacetyl Baccatin III is a novel stable derivative of 10-Deacetylbaccatin III (D198250) with antitumor and antimitotic activity.

REFERENCES

• Appendino, G., et al.: Gazzetta Chimica Italiana, 124, 253 (1994)