Marizomib

Synopsis, 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 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 Formula	C₁₅H₂₀ClNO₄
Molecular Weight	313.77 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	313.1080858 g/mol
Monoisotopic Mass	313.1080858 g/mol
Topological Polar Surface Area	75.6 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	508
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1