(4S,7R,8S,9S,13Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

• ChemBase ID: 168109
• Molecular Formular: C27H41NO5S
• Molecular Mass: 491.68314
• Monoisotopic Mass: 491.27054442
• SMILES: C\1=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)/C
• Canonical SMILES: O=C1OC(C/C=C(/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/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22?,23-,25-/m0/s1
• InChIKey: XOZIUKBZLSUILX-AEEURSPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,7R,8S,9S,13Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• IUPAC Traditional name: (4S,7R,8S,9S,13Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• Synonyms: (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione; (-)-Desoxyepothilone B; (-)-Epothilone D; 12,13-Deoxyepothilone B; 12,13-Desoxyepothilone B; Desoxyepothilone B; Epo D; Epothilone D; KOS 862; NSC 703147; Epothilone D (synthetic)

Database IDs

• CAS Number: 189453-10-9
• PubChem SID: 162262241
• PubChem CID: 6440032

CALCULATED PROPERTIES

• Acid pKa: 14.086924
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.0955997
• LogD (pH = 7.4): 5.0963
• Log P: 5.096309
• Molar Refractivity: 136.0431 cm^3
• Polarizability: 53.16778 Å^3
• Polar Surface Area: 96.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ether; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 63-66°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E589000

Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumou

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)