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Chemistry

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Also known as: Salinosporamide a, 437742-34-2, Npi-0052, (-)-salinosporamide a, Npi 0052, Ml 858
Molecular Formula
C15H20ClNO4
Molecular Weight
313.77  g/mol
InChI Key
NGWSFRIPKNWYAO-SHTIJGAHSA-N
FDA UNII
703P9YDP7F

Marizomib
Marizomib is a naturally-occurring salinosporamide, isolated from the marine actinomycete Salinospora tropica, with potential antineoplastic activity. Marizomib irreversibly binds to and inhibits the 20S catalytic core subunit of the proteasome by covalently modifying its active site threonine residues; inhibition of ubiquitin-proteasome mediated proteolysis results in an accumulation of poly-ubiquitinated proteins, which may result in the disruption of cellular processes, cell cycle arrest, the induction of apoptosis, and the inhibition of tumor growth and angiogenesis. This agent more may more potent and selective than the proteasome inhibitor bortezomib.
1 2D Structure

Marizomib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
2.1.2 InChI
InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1
2.1.3 InChI Key
NGWSFRIPKNWYAO-SHTIJGAHSA-N
2.1.4 Canonical SMILES
CC12C(C(=O)NC1(C(=O)O2)C(C3CCCC=C3)O)CCCl
2.1.5 Isomeric SMILES
C[C@]12[C@H](C(=O)N[C@]1(C(=O)O2)[C@H]([C@H]3CCCC=C3)O)CCCl
2.2 Other Identifiers
2.2.1 UNII
703P9YDP7F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Homosalinosporamide A

2. Npi 0052

3. Npi-0052

4. Salinosporamide A

2.3.2 Depositor-Supplied Synonyms

1. Salinosporamide A

2. 437742-34-2

3. Npi-0052

4. (-)-salinosporamide A

5. Npi 0052

6. Ml 858

7. Salinosporamide A (npi-0052, Marizomib)

8. 703p9ydp7f

9. Chebi:48045

10. (1r,4r,5s)-4-(2-chloroethyl)-1-((s)-((s)-cyclohex-2-en-1-yl)(hydroxy)methyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

11. (1r,4r,5s)-4-(2-chloroethyl)-1-[(s)-(1s)-cyclohex-2-en-1-yl(hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

12. Marizomib [usan:inn]

13. Marizomibum

14. Unii-703p9ydp7f

15. Homosalinosporamide A

16. Marizomib [inn]

17. Marizomib (usan/inn)

18. Marizomib [usan]

19. Marizomib [who-dd]

20. Schembl151667

21. Salinosporamide A [mi]

22. Chembl371405

23. Dtxsid00904019

24. (1s,2r,5r)-2-(2-chloroethyl)-5-[(s)-[(1s)-cyclohex-2-en-1-yl]-hydroxymethyl]-1-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione

25. Ex-a3259

26. Zinc3990364

27. Bdbm50398608

28. Akos027323566

29. Db11762

30. Hy-10985

31. Cs-0002986

32. D09640

33. A872651

34. Q7404722

35. (1r,4r,5s)-4-(2-chloroethyl)-1-((s)-((1s)-cyclohex-2-en-1-yl)hydroxymethyl)-5-methyl- 6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione

36. (1r,4r,5s)-4-(2-chloroethyl)-1-((s)-((s)-cyclohex-2-enyl)(hydroxy)methyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

37. (1r,4r,5s)-4-(2-chloroethyl)-1-[(s)-[(1s)-cyclohex-2-en-1-yl]-hydroxymethyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

38. 6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione, 4-(2-chloroethyl)-1-((s)-(1s)-2-cyclohexen-1-ylhydroxymethyl)-5-methyl-, (1r,4r,5s)-

39. 6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione, 4-(2-chloroethyl)-1-((s)-(1s)-2-cyclohexen-1-ylhydroxymethyl)-5-methyl-, (1r,4r,5s)-

2.4 Create Date
2006-10-26
3 Chemical and Physical Properties
Molecular Weight 313.77 g/mol
Molecular Formula C15H20ClNO4
XLogP31.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass313.1080858 g/mol
Monoisotopic Mass313.1080858 g/mol
Topological Polar Surface Area75.6 Ų
Heavy Atom Count21
Formal Charge0
Complexity508
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Treatment of malignant glial tumours


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