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Chemistry

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Also known as: 1801344-14-8, Emavusertib [inn], Mh5dmf9jky, Ca4948, Au-4948, (r)-n-(5-(3-hydroxypyrrolidin-1-yl)-2-morpholinooxazolo[4,5-b]pyridin-6-yl)-2-(2-methylpyridin-4-yl)oxazole-4-carboxamide
Molecular Formula
C24H25N7O5
Molecular Weight
491.5  g/mol
InChI Key
SJHNWSAWWOAWJH-MRXNPFEDSA-N
FDA UNII
MH5DMF9JKY

Emavusertib
Emavusertib is an orally bioavailable, reversible inhibitor of interleukin-1 receptor-associated kinase 4 (IRAK4), with potential antineoplastic, immunomodulating and anti-inflammatory activities. Upon oral administration, emavusertib targets, binds to, and blocks the kinase activity of IRAK4. This inhibits IRAK4-mediated signaling, prevents the activation of IRAK4-mediated nuclear factor-kappa B (NF-kB) signaling and decreases the expression of inflammatory cytokines and certain pro-survival factors. This inhibits proliferation of IRAK4-overactivated tumor cells, which are found in cells harboring MYD88 activating mutations or those with overactivated toll-like receptor (TLR) pathways. In addition, CA-4948 may inhibit inflammation and immune-mediated cell destruction in inflammatory and auto-immune diseases where TLR or interleukin 1 receptor (IL-1R) signaling is overactivated and MYD88 is dysregulated. IRAK4, a serine/threonine-protein kinase that plays a key role in both the TLR and IL-1R signaling pathways, is activated though the adaptor protein MYD88 and links the TLR and IL-1R signaling pathway to the NF-kB pathway.
1 2D Structure

Emavusertib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[5-[(3R)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide
2.1.2 InChI
InChI=1S/C24H25N7O5/c1-14-10-15(2-4-25-14)23-27-18(13-35-23)22(33)26-17-11-19-20(28-21(17)31-5-3-16(32)12-31)29-24(36-19)30-6-8-34-9-7-30/h2,4,10-11,13,16,32H,3,5-9,12H2,1H3,(H,26,33)/t16-/m1/s1
2.1.3 InChI Key
SJHNWSAWWOAWJH-MRXNPFEDSA-N
2.1.4 Canonical SMILES
CC1=NC=CC(=C1)C2=NC(=CO2)C(=O)NC3=CC4=C(N=C3N5CCC(C5)O)N=C(O4)N6CCOCC6
2.1.5 Isomeric SMILES
CC1=NC=CC(=C1)C2=NC(=CO2)C(=O)NC3=CC4=C(N=C3N5CC[C@H](C5)O)N=C(O4)N6CCOCC6
2.2 Other Identifiers
2.2.1 UNII
MH5DMF9JKY
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 1801344-14-8

2. Emavusertib [inn]

3. Mh5dmf9jky

4. Ca4948

5. Au-4948

6. (r)-n-(5-(3-hydroxypyrrolidin-1-yl)-2-morpholinooxazolo[4,5-b]pyridin-6-yl)-2-(2-methylpyridin-4-yl)oxazole-4-carboxamide

7. Chembl4783351

8. 4-oxazolecarboxamide, N-[5-[(3r)-3-hydroxy-1-pyrrolidinyl]-2-(4-morpholinyl)oxazolo[4,5-b]pyridin-6-yl]-2-(2-methyl-4-pyridinyl)-

9. N-[5-[(3r)-3-hydroxypyrrolidin-1-yl]-2-morpholin-4-yl-[1,3]oxazolo[4,5-b]pyridin-6-yl]-2-(2-methylpyridin-4-yl)-1,3-oxazole-4-carboxamide

10. 2-(2-methylpyridin-4-yl)-n-[2-morpholin-4-yl-5-[(3r)-3-oxidanylpyrrolidin-1-yl]-[1,3]oxazolo[4,5-b]pyridin-6-yl]-1,3-oxazole-4-carboxamide

11. 4-oxazolecarboxamide, N-(5-((3r)-3-hydroxy-1-pyrrolidinyl)-2-(4-morpholinyl)oxazolo(4,5-b)pyridin-6-yl)-2-(2-methyl-4-pyridinyl)-

12. N-(5-((3r)-3-hydroxy-1-pyrrolidinyl)-2-(4-morpholinyl)oxazolo(4,5-b)pyridin-6-yl)-2-(2-methyl-4-pyridinyl)-4-oxazolecarboxamide

13. N-(5-((3r)-3-hydroxypyrrolidin-1-yl)-2-(morpholin-4- Yl)(1,3)oxazolo(4,5-b)pyridin-6-yl)-2-(2-methylpyridin-4- Yl)-1,3-oxazole-4-carboxamide

14. N-[5-[(3r)-3-hydroxy-1-pyrrolidinyl]-2-(4-morpholinyl)oxazolo[4,5-b]pyridin-6-yl]-2-(2-methyl-4-pyridinyl)-4-oxazolecarboxamide

15. Emavusertib [usan]

16. Unii-mh5dmf9jky

17. Emavusertib(ca-4948)

18. Emavusertib (ca-4948)

19. Schembl16896638

20. Gtpl10152

21. Dtxsid001103300

22. Ex-a4736

23. Au4948

24. Bdbm50547964

25. Nsc824184

26. S9779

27. Who 11558

28. Nsc-824184

29. Compound 24 [pmid: 33335659]

30. Ac-36757

31. Hy-135317

32. Cs-0111301

33. A937061

34. Fj0

2.4 Create Date
2016-02-23
3 Chemical and Physical Properties
Molecular Weight 491.5 g/mol
Molecular Formula C24H25N7O5
XLogP31.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count5
Exact Mass491.19171692 g/mol
Monoisotopic Mass491.19171692 g/mol
Topological Polar Surface Area143 Ų
Heavy Atom Count36
Formal Charge0
Complexity773
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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