ACT-1014-6470   Click here for help

GtoPdb Ligand ID: 12326

Synonyms: example 172 [WO2019137927A1] [2] | Ic-58 [2]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: ACT-1014-6470 is a novel, orally available small molecule anatgonist of the complement factor 5a receptor 1 (C5a1 receptor) [4]. It was designed for anti-inflammatory activity, for application in autoimmune diseases. ACT-1014-6470 selectively targets C5a-mediated receptor signalling, in contrast to the clinically used anti-C5 monoclonals eculizumab and ravulizumab that prevent C5a (anaphylatoxin) and C5b production. The principal effect of both strategies is to block further activation of complement-mediated inflammation. One suggested benefit of the small-molecule approach is that it does not alter C5b-mediated membrane attack complex (MAC) formation, which means that the bactericidal activity of the complement system remains intact.

n.b. Avacopan (CCX-168) was the first C5a1 receptor antagonist to be approved by the FDA (2021).
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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 5
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 44.61
Molecular weight 565.23
XLogP 7.03
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 O=C1N(Cc2c(N1Cc1ccccc1C(F)(F)F)nn(c2)CC(F)(F)C)C1CCN(CC1)c1c(C)cccc1F
Isomeric SMILES FC(Cn1nc2N(C(=O)N(Cc2c1)C1CCN(CC1)c1c(cccc1C)F)Cc1c(cccc1)C(F)(F)F)(C)F
InChI InChI=1S/C28H29F6N5O/c1-18-6-5-9-23(29)24(18)36-12-10-21(11-13-36)38-16-20-14-37(17-27(2,30)31)35-25(20)39(26(38)40)15-19-7-3-4-8-22(19)28(32,33)34/h3-9,14,21H,10-13,15-17H2,1-2H3
InChI Key YPWBQOVYMUEXJT-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-(2,2-difluoropropyl)-5-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-7-[[2-(trifluoromethyl)phenyl]methyl]-4H-pyrazolo[3,4-d]pyrimidin-6-one
Synonyms Click here for help
example 172 [WO2019137927A1] [2] | Ic-58 [2]
Database Links Click here for help
Specialist databases
GPCRdb Ligand ACT-1014-6470
Other databases
GtoPdb PubChem SID 479821117
PubChem CID 142620206
Search Google for chemical match using the InChIKey YPWBQOVYMUEXJT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YPWBQOVYMUEXJT
UniChem Compound Search for chemical match using the InChIKey YPWBQOVYMUEXJT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YPWBQOVYMUEXJT-UHFFFAOYSA-N