Also known as: 865783-99-9, On-014185, Briciclib (on-013105), On 014185, Briciclib (on-014185), 865783-99-9 (free acid)

Molecular Formula

C₁₉H₂₃O₁₀PS

Molecular Weight

474.4 g/mol

InChI Key

LXENKEWVEVKKGV-BQYQJAHWSA-N

FDA UNII

WG93X96336

Briciclib is a benzyl styryl sulfone analog, and a phosphate ester prodrug of ON 013100, with potential antineoplastic activity. Upon hydrolysis, briciclib is converted to ON 013100, which blocks cyclin D mRNA translation and decreases protein expression of cyclin D. This may induce cell cycle arrest and apoptosis in cancer cells overexpressing cyclin D and eventually decrease tumor cell proliferation. Cyclin D, a member of the cyclin family of cell cycle regulators, plays a key role in cell cycle division and is often overexpressed in a variety of hematologic and solid tumors and is correlated with poor prognosis. suppresses cyclin D1 accumulation in cancer cells.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-methoxy-5-[[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]phenyl] dihydrogen phosphate

2.1.2 InChI

InChI=1S/C19H23O10PS/c1-25-14-10-17(27-3)15(18(11-14)28-4)7-8-31(23,24)12-13-5-6-16(26-2)19(9-13)29-30(20,21)22/h5-11H,12H2,1-4H3,(H2,20,21,22)/b8-7+

2.1.3 InChI Key

LXENKEWVEVKKGV-BQYQJAHWSA-N

2.1.4 Canonical SMILES

COC1=C(C=C(C=C1)CS(=O)(=O)C=CC2=C(C=C(C=C2OC)OC)OC)OP(=O)(O)O

2.1.5 Isomeric SMILES

COC1=C(C=C(C=C1)CS(=O)(=O)/C=C/C2=C(C=C(C=C2OC)OC)OC)OP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

WG93X96336

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 865783-99-9

2. On-014185

3. Briciclib (on-013105)

4. On 014185

5. Briciclib (on-014185)

6. 865783-99-9 (free Acid)

7. Wg93x96336

8. (e)-2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl Dihydrogen Phosphate

9. Phenol, 2-methoxy-5-((((1e)-2-(2,4,6-trimethoxyphenyl)ethenyl)sulfonyl)methyl)-, 1-(dihydrogen Phosphate)

10. Phenol, 2-methoxy-5-[[[(1e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl]methyl]-, 1-(dihydrogen Phosphate)

11. Briciclib [usan:inn]

12. On-013105

13. Unii-wg93x96336

14. Briciclib [usan]

15. Briciclib [inn]

16. Briciclib (usan/inn)

17. Briciclib [who-dd]

18. Briciclib; On 014185

19. Schembl1634579

20. Schembl1634581

21. Chembl1206245

22. [2-methoxy-5-[[(e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonylmethyl]phenyl] Dihydrogen Phosphate

23. Amy42169

24. Bcp17292

25. Ex-a2492

26. Mfcd22665751

27. S6533

28. Zinc28965775

29. Cs-5589

30. Db12004

31. Ac-36098

32. Hy-16366

33. Briciclib(on 013105,on 014185)

34. D10614

35. Q27292622

36. (2-methoxy-5-{[(e)-2-(2,4,6-trimethoxyphenyl)ethenesulfonyl]methyl}phenoxy)phosphonic Acid

37. (e)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl Dihydrogen Phosphate

38. On013105; On-013105; On 013105;on-014185;on 014185;on014185

39. (e)-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)-2-methoxyphenyl Dihydrogen Phosphate

40. 2-methoxy-5-(((2-(2,4,6-trimethoxyphenyl)ethenyl)sulfonyl)methyl)phenyl Dihydrogen Phosphate

41. Phenol, 2-methoxy-5-[[[(1e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl] Methyl]-, 1-(dihydrogen Phosphate)

42. Phenol,2-methoxy-5-[[[(1e)-2-(2,4,6-trimethoxyphenyl)ethenyl]sulfonyl]methyl]-,1-(dihydrogen Phosphate)

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₃O₁₀PS
Molecular Weight	474.4 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	10
Exact Mass	474.07495510 g/mol
Monoisotopic Mass	474.07495510 g/mol
Topological Polar Surface Area	146 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	717
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

ON 013105

ON 013105

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