MRI-1867   Click here for help

GtoPdb Ligand ID: 10521

Synonyms: (-)-MRI-1867 | MRI1867
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: MRI-1867 is a hybrid molecule that acts both as an inverse agonist of peripheral cannabinoid receptor 1 (CB1) and as an inhibitor of inducible nitric oxide synthase (iNOS) [1]. It is orally active, and the (S)-enantiomer is the more active form of the molecule. MRI-1867 was initially shown to exhibit anti-fibrotic activity in mouse models of liver fibrosis [1] and it has subsequently been demonstrated to reduce signs of inflammation, fibrosis, oxidative stress and overall renal injury in a mouse model of obesity-induced chronic kidney disease [2]. The therapeutic effect of MRI-1867 is two-fold; it both reduces fibrotic progression and is able to attenuate established fibrosis. Activities at both of its molecular targets are involved in mediating its in vivo efficacy.
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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 7
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 108.86
Molecular weight 513.08
XLogP 5.32
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 Clc1ccc(cc1)C1=NN(CC1c1ccccc1)C(=NS(=O)(=O)c1ccc(cc1)Cl)N=C(N)C
Isomeric SMILES Clc1ccc(cc1)C1=NN(C[C@@H]1c1ccccc1)/C(=N/S(=O)(=O)c1ccc(cc1)Cl)/N=C(\N)/C
InChI InChI=1S/C24H21Cl2N5O2S/c1-16(27)28-24(30-34(32,33)21-13-11-20(26)12-14-21)31-15-22(17-5-3-2-4-6-17)23(29-31)18-7-9-19(25)10-8-18/h2-14,22H,15H2,1H3,(H2,27,28,30)/t22-/m1/s1
InChI Key GZPQTZIUWCQXCF-JOCHJYFZSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(4S)-N-(1-aminoethylidene)-5-(4-chlorophenyl)-N'-(4-chlorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide
Synonyms Click here for help
(-)-MRI-1867 | MRI1867
Database Links Click here for help
Specialist databases
GPCRdb Ligand MRI-1867
Other databases
GtoPdb PubChem SID 387065603
PubChem CID 132937648
Search Google for chemical match using the InChIKey GZPQTZIUWCQXCF-JOCHJYFZSA-N
Search Google for chemicals with the same backbone GZPQTZIUWCQXCF
UniChem Compound Search for chemical match using the InChIKey GZPQTZIUWCQXCF-JOCHJYFZSA-N
UniChem Connectivity Search for chemical match using the InChIKey GZPQTZIUWCQXCF-JOCHJYFZSA-N