C391   Click here for help

GtoPdb Ligand ID: 9570

Synonyms: compound 5 [PMID: 27994760]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: C391 is a protease activated receptor 2 (PAR2) antagonist [5]. It is a small peptidomimetic derivative of the PAR2 agonist 2-furoyl-LIGRLO-amide [1]. PAR2 antagonists have potential for treating inflammatory, respiratory, gastrointestinal, neurological, and metabolic disorders.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 6
Rotatable bonds 22
Topological polar surface area 244.92
Molecular weight 767.39
XLogP -0.5
No. Lipinski's rules broken 3
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Canonical SMILES NCCCCC(N1CC2N(CC1=O)C(=O)C(CN2C(=O)c1ccco1)NC(=O)CC(C)C)C(=O)NC(C(=O)NC(C(=O)O)Cc1ccc(cc1)O)CC(C)C
Isomeric SMILES NCCCC[C@H](N1CC2N(CC1=O)C(=O)[C@H](CN2C(=O)c1ccco1)NC(=O)CC(C)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)O)CC(C)C
InChI InChI=1S/C38H53N7O10/c1-22(2)16-26(34(49)42-27(38(53)54)18-24-10-12-25(46)13-11-24)41-35(50)29(8-5-6-14-39)43-20-32-44(37(52)30-9-7-15-55-30)19-28(40-31(47)17-23(3)4)36(51)45(32)21-33(43)48/h7,9-13,15,22-23,26-29,32,46H,5-6,8,14,16-21,39H2,1-4H3,(H,40,47)(H,41,50)(H,42,49)(H,53,54)/t26-,27-,28-,29-,32?/m0/s1
1. Boitano S, Hoffman J, Flynn AN, Asiedu MN, Tillu DV, Zhang Z, Sherwood CL, Rivas CM, DeFea KA, Vagner J et al.. (2015)
The novel PAR2 ligand C391 blocks multiple PAR2 signalling pathways in vitro and in vivo.
Br J Pharmacol, 172 (18): 4535-4545. [PMID:26140338]
2. Cocks TM, Moffatt JD. (2000)
Protease-activated receptors: sentries for inflammation?.
Trends Pharmacol Sci, 21 (3): 103-8. [PMID:10689364]
3. Ferrell WR, Lockhart JC, Kelso EB, Dunning L, Plevin R, Meek SE, Smith AJ, Hunter GD, McLean JS, McGarry F et al.. (2003)
Essential role for proteinase-activated receptor-2 in arthritis.
J Clin Invest, 111 (1): 35-41. [PMID:12511586]
4. Kanke T, Takizawa T, Kabeya M, Kawabata A. (2005)
Physiology and pathophysiology of proteinase-activated receptors (PARs): PAR-2 as a potential therapeutic target.
J Pharmacol Sci, 97 (1): 38-42. [PMID:15655295]
5. Yau MK, Liu L, Suen JY, Lim J, Lohman RJ, Jiang Y, Cotterell AJ, Barry GD, Mak JY, Vesey DA et al.. (2016)
PAR2 Modulators Derived from GB88.
ACS Med Chem Lett, 7 (12): 1179-1184. [PMID:27994760]