(1S,3S,7R,10S,11R,12S,16S)-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: 2717
• Molecular Formular: C27H41NO6S
• Molecular Mass: 507.68254
• Monoisotopic Mass: 507.26545904
• SMILES: C[C@H]1CCC[C@]2(C)O[C@H]2C[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
• Canonical SMILES: O=C1O[C@@H](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-TYFQHMATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,7R,10S,11R,12S,16S)-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: @epothilone B
• Synonyms: patupilone; EPO 906; EPO906; Epothilone B

Database IDs

• CAS Number: 152044-54-7
• PubChem SID: 46505629; 160966166
• PubChem CID: 46936553

CALCULATED PROPERTIES

JChem

• 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: 109.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.7
• LOG S: -5.17
• Solubility (Water): 3.42e-03 g/l

DETAILS

DrugBank - DB03010

• Drug Groups: experimental; investigational
• Description: Epothilone B is a 16-membered macrolide that mimics the biological effects of taxol.
• Indication: Investigated for use/treatment in ovarian cancer, lung cancer, brain cancer, breast cancer, and gastric cancer.
• Affected Organisms: Humans and other mammals