(1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-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: 168107
• Molecular Formular: C26H39NO6S
• Molecular Mass: 493.65596
• Monoisotopic Mass: 493.24980897
• SMILES: [C@@H]12[C@@H](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
• Canonical SMILES: O=C1OC(C[C@@H]2O[C@@H]2CCC[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/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20?,21-,22-,24-/m0/s1
• InChIKey: HESCAJZNRMSMJG-XOVLCIRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-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: (-)-epothilone A
• Synonyms: (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione; (-)-Epothilone A; Epothilone A; Epothilone A

Database IDs

• CAS Number: 152044-53-6
• PubChem SID: 162262239
• PubChem CID: 49852287

CALCULATED PROPERTIES

• Acid pKa: 14.086929
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.8414474
• LogD (pH = 7.4): 3.842148
• Log P: 3.8421571
• Molar Refractivity: 130.1218 cm^3
• Polarizability: 51.57048 Å^3
• Polar Surface Area: 105.95 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E588980

The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of

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)