4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate

• ChemBase ID: 105327
• Molecular Formular: C31H38O11
• Molecular Mass: 586.62682
• Monoisotopic Mass: 586.24141204
• SMILES: CC(=O)OC1C(=O)C2(C)C(O)CC3OCC3(OC(=O)C)C2C(OC(=O)c2ccccc2)C2(O)CC(O)C(=C1C2(C)C)C
• Canonical SMILES: CC(=O)OC1C(=O)C2(C)C(O)CC3C(C2C(C2(C(C1=C(C)C(O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
• InChI: InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3
• InChIKey: OVMSOCFBDVBLFW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: 4,12-bis(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate
• Synonyms: BACCATINE III

Database IDs

• CAS Number: 27548-93-2
• PubChem SID: 162092321
• PubChem CID: 4357887

CALCULATED PROPERTIES

• Acid pKa: 9.661471
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.042699
• LogD (pH = 7.4): 1.0403587
• Log P: 1.0427289
• Molar Refractivity: 145.3486 cm^3
• Polarizability: 58.259655 Å^3
• Polar Surface Area: 165.89 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

DETAILS

MP Biomedicals - 02159793

Starting material for taxol derivatives.

REFERENCES

• Wheeler, N.C., J. Natl. Prod. , 55 : 432, (1992).