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Also known as: 1224095-98-0, Brilacidin [usan], Pmx30063 free base, Pmx-30063 free base, Brilacidin (usan), I1679x069h

Molecular Formula

C₄₀H₅₀F₆N₁₄O₆

Molecular Weight

936.9 g/mol

InChI Key

QPDYBCZNGUJZDK-DNQXCXABSA-N

FDA UNII

I1679X069H

Brilacidin is a synthetic, nonpeptidic, small molecule mimetic of defensin, a type of host defense proteins/peptides (HDPs) or antimicrobial peptides (AMPs), with potential antibacterial and antiviral activities. Upon administration, brilacidin selectively destabilizes bacterial and viral membrane integrity, which leads to their proteolysis and degradation. HDPs are part of the innate immune response and act as the first line of defense against foreign pathogens. Severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) infection has been shown to suppress defensins.

1 2D Structure

Brilacidin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-N,6-N-bis[3-[5-(diaminomethylideneamino)pentanoylamino]-2-[(3R)-pyrrolidin-3-yl]oxy-5-(trifluoromethyl)phenyl]pyrimidine-4,6-dicarboxamide

2.1.2 InChI

InChI=1S/C40H50F6N14O6/c41-39(42,43)21-13-25(57-31(61)5-1-3-9-53-37(47)48)33(65-23-7-11-51-18-23)27(15-21)59-35(63)29-17-30(56-20-55-29)36(64)60-28-16-22(40(44,45)46)14-26(34(28)66-24-8-12-52-19-24)58-32(62)6-2-4-10-54-38(49)50/h13-17,20,23-24,51-52H,1-12,18-19H2,(H,57,61)(H,58,62)(H,59,63)(H,60,64)(H4,47,48,53)(H4,49,50,54)/t23-,24-/m1/s1

2.1.3 InChI Key

QPDYBCZNGUJZDK-DNQXCXABSA-N

2.1.4 Canonical SMILES

C1CNCC1OC2=C(C=C(C=C2NC(=O)C3=CC(=NC=N3)C(=O)NC4=CC(=CC(=C4OC5CCNC5)NC(=O)CCCCN=C(N)N)C(F)(F)F)C(F)(F)F)NC(=O)CCCCN=C(N)N

2.1.5 Isomeric SMILES

C1CNC[C@@H]1OC2=C(C=C(C=C2NC(=O)C3=CC(=NC=N3)C(=O)NC4=CC(=CC(=C4O[C@@H]5CCNC5)NC(=O)CCCCN=C(N)N)C(F)(F)F)C(F)(F)F)NC(=O)CCCCN=C(N)N

2.2 Other Identifiers

2.2.1 UNII

I1679X069H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Brilacidin Tetrahydrochloride

2. N4,n6-bis(3-((5-(carbamimidoylamino)pentanoyl)amino(-2-((3r)-pyrrolidin-3-yloxy)-5-(trifluoromethyl)phenyl)pyrimidine-4,6-dicarboxamide

3. Pmx 30063

4. Pmx-30063

5. Pmx-30063 Free Base

6. Pmx30063

7. Pmx30063 Free Base

2.3.2 Depositor-Supplied Synonyms

1. 1224095-98-0

2. Brilacidin [usan]

3. Pmx30063 Free Base

4. Pmx-30063 Free Base

5. Brilacidin (usan)

6. I1679x069h

7. 4,6-pyrimidinedicarboxamide, N4,n6-bis(3-((5-((aminoiminomethyl)amino)-1-oxopentyl)amino)-2-((3r)-3-pyrrolidinyloxy)-5-(trifluoromethyl)phenyl)-

8. N4,n6-bis(3-(5-guanidinopentanamido)-2-(((r)-pyrrolidin-3-yl)oxy)-5-(trifluoromethyl)phenyl)pyrimidine-4,6-dicarboxamide

9. Brilacidin [usan:inn]

10. Unii-i1679x069h

11. Brilacidin [inn]

12. Brilacidin [who-dd]

13. Schembl2878543

14. Chembl2219413

15. Dtxsid90153594

16. Glxc-25591

17. Cs-6677

18. Db12997

19. Hy-19892

20. D10414

21. Q15408420

22. 4-n,6-n-bis[3-[5-(diaminomethylideneamino)pentanoylamino]-2-[(3r)-pyrrolidin-3-yl]oxy-5-(trifluoromethyl)phenyl]pyrimidine-4,6-dicarboxamide

23. N,n'-bis(3-((5-(carbamimidoylamino)pentanoyl)amino(-2-((3r)-pyrrolidin-3-yloxy)-5-(trifluoromethyl)phenyl)pyrimidine-4,6-dicarboxamide

24. N,n'-bis(3-((5-(carbamimidoylamino)pentanoyl)amino)-2-((3r)-pyrrolidin-3-yloxy)-5-(trifluoromethyl)phenyl)pyrimidine-4,6-dicarboxamide

2.4 Create Date

2008-11-10

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₅₀F₆N₁₄O₆
Molecular Weight	936.9 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	20
Exact Mass	936.39419434 g/mol
Monoisotopic Mass	936.39419434 g/mol
Topological Polar Surface Area	314 Å²
Heavy Atom Count	66
Formal Charge	0
Complexity	1560
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)