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

• ChemBase ID: 161096
• Molecular Formular: C37H46O14
• Molecular Mass: 714.75274
• Monoisotopic Mass: 714.28875615
• SMILES: C1(=C2C([C@@](C[C@@H]1OC(=O)C)([C@H]([C@H]1[C@]([C@H]([C@H]2OC(=O)C)OC(=O)C)([C@@H](C[C@@H]2[C@]1(CO2)OC(=O)C)OC(=O)C)C)OC(=O)c1ccccc1)O)(C)C)C
• Canonical SMILES: CC(=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@H]([C@H](C(=C1C)C2(C)C)OC(=O)C)OC(=O)C)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C37H46O14/c1-18-25(46-19(2)38)16-37(44)32(50-33(43)24-13-11-10-12-14-24)30-35(9,26(47-20(3)39)15-27-36(30,17-45-27)51-23(6)42)31(49-22(5)41)29(48-21(4)40)28(18)34(37,7)8/h10-14,25-27,29-32,44H,15-17H2,1-9H3/t25-,26+,27+,29-,30-,31-,32-,35+,36-,37+/m0/s1
• InChIKey: UJFKTEIDORFVQS-XYEQATCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,7R,9R,10S,11R,12S,15S)-4,9,11,12,15-pentakis(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-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,9R,10S,11R,12S,15S)-4,9,11,12,15-pentakis(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: (2aR,4S,4aS,5R,6R,9S,11S,12S,12aR,12bS)-2a,3,4,4a,5,6,9,10,12,12a-Decahydro-4a,8,13,13-tetramethyl-4,5,6,9,12b-pentaacetate 12-Benzoate Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete-4,5,6,9,11,12,12b-heptol; Baccatin VI

Database IDs

• CAS Number: 57672-79-4
• PubChem SID: 162255231
• PubChem CID: 71313612

CALCULATED PROPERTIES

• Acid pKa: 13.272718
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.5987397
• LogD (pH = 7.4): 1.5987391
• Log P: 1.5987397
• Molar Refractivity: 173.4947 cm^3
• Polarizability: 70.3602 Å^3
• Polar Surface Area: 187.26 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B101030

A taxane derivative, a neoplasm inhibitor to ovarian and breast cancers found in Taxus species.

REFERENCES

• Katkovcinova, Z., et al.: J. Biosci., 63, 721 (2008)
• Tian, J., et al.: J. Pharm. Sci., 97, 3100 (2008)
• Miao, Z., et al.: App. Biochem. Microbiol., 45, 81 (2008)