(1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

• ChemBase ID: 168108
• Molecular Formular: C27H41NO6S
• Molecular Mass: 507.68254
• Monoisotopic Mass: 507.26545904
• SMILES: [C@@H]12[C@@](CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](CC(=O)OC(C1)/C(=C/c1csc(n1)C)/C)O)(C)C)C)O)C)(O2)C
• Canonical SMILES: O=C1OC(C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
• InChI: InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20?,21-,22-,24-,27+/m0/s1
• InChIKey: QXRSDHAAWVKZLJ-HPZHUWBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• IUPAC Traditional name: (1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• Synonyms: (-)-Epothilone B; EPO 906; EPO 906A; Epothilone B; Patupilone; Epothilone B (synthetic); (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Database IDs

• CAS Number: 152044-54-7
• PubChem SID: 162262240
• PubChem CID: 60018621

CALCULATED PROPERTIES

• Acid pKa: 14.086929
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 4.122024
• LogD (pH = 7.4): 4.1227245
• Log P: 4.1227336
• Molar Refractivity: 134.76 cm^3
• Polarizability: 53.40498 Å^3
• Polar Surface Area: 105.95 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Ethanol; Methanol
• Apperance: White Powder
• Melting Point: 95-97°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E588990

Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone B is what is known as a microtubule stabilizer. When a cell divides, the c

REFERENCES

• Bollag, D.M., et al.: Cancer. Res., 55, 2325 (1995)
• Hardt, I.H., et al.: J. Nat. Prod., 64, 847 (1995)
• Gerth, K., et al.: J. Antibiot., 55, 41, 45 (2002)