(4R,7S,8R,9S,13Z,16R)-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: 1642
• Molecular Formular: C27H41NO5S
• Molecular Mass: 491.68314
• Monoisotopic Mass: 491.27054442
• SMILES: C[C@H]1CCC/C(=C\C[C@@H](OC(=O)C[C@@H](O)C(C)(C)C(=O)[C@@H](C)[C@@H]1O)/C(=C/c1csc(C)n1)/C)/C
• Canonical SMILES: O=C1O[C@H](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-UKMAFROXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7S,8R,9S,13Z,16R)-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: @epothilone D
• Synonyms: epothilone D; KOS-862; Epothilone D

Database IDs

• CAS Number: 189453-10-9
• PubChem SID: 160965099; 46508361
• PubChem CID: 46936246

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 4.54
• LOG S: -5.3
• Solubility (Water): 2.46e-03 g/l

DETAILS

DrugBank - DB01873

• Drug Groups: experimental; investigational
• Indication: Investigated for use/treatment in colorectal cancer, lung cancer, breast cancer, solid tumors, and prostate cancer.
• External Links: Wikipedia