SCH-79797   Click here for help

GtoPdb Ligand ID: 10971

Synonyms: SCH 79797 | SCH79797
Compound class: Synthetic organic
Comment: Potent, selective non-peptide PAR1 antagonist. Marketed as SCH-79797 dihydrochloride.

Other biological activity: SCH-79797 has been reported to exhibit antibacterial activity against Gram-positive and -negative bacteria, including MRSA and other clinically significant bacterial pathogens, with a low frequency of resistance in vivo [2]. The authors show that SCH-79797 targets both bacterial folate metabolism and membrane integrity to mediate its antibacterial effect.
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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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Click here for structure editor
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 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 68.76
Molecular weight 371.21
XLogP 5.48
No. Lipinski's rules broken 1
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 CC(c1ccc(cc1)Cn1ccc2c1ccc1c2c(N)nc(n1)NC1CC1)C
Isomeric SMILES CC(c1ccc(cc1)Cn1ccc2c1ccc1c2c(N)nc(n1)NC1CC1)C
InChI InChI=1S/C23H25N5/c1-14(2)16-5-3-15(4-6-16)13-28-12-11-18-20(28)10-9-19-21(18)22(24)27-23(26-19)25-17-7-8-17/h3-6,9-12,14,17H,7-8,13H2,1-2H3,(H3,24,25,26,27)
InChI Key AVXQPEKZIGPIJW-UHFFFAOYSA-N
References
1. Ahn HS, Foster C, Boykow G, Stamford A, Manna M, Graziano M. (2000)
Inhibition of cellular action of thrombin by N3-cyclopropyl-7-[[4-(1-methylethyl)phenyl]methyl]-7H-pyrrolo[3, 2-f]quinazoline-1,3-diamine (SCH 79797), a nonpeptide thrombin receptor antagonist.
Biochem Pharmacol, 60 (10): 1425-34. [PMID:11020444]
2. Martin 2nd JK, Sheehan JP, Bratton BP, Moore GM, Mateus A, Li SH, Kim H, Rabinowitz JD, Typas A, Savitski MM et al.. (2020)
A Dual-Mechanism Antibiotic Kills Gram-Negative Bacteria and Avoids Drug Resistance.
Cell, 181 (7): 1518-1532.e14. [PMID:32497502]