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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key OHQDORKALTUSJJ-ZHLQKWORSA-N
References
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]