VERCIRNON

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Search structure


Synonyms	CCX-282-B CCX282 GSK-1605786 GSK1605786 Vercirnon Verecimon
Status
Molecule Category	UNKNOWN
UNII	MWI54OUA12
EPA CompTox	DTXSID50220135


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	JRWROCIMSDXGOZ-UHFFFAOYSA-N
Smiles	CC(C)(C)c1ccc(S(=O)(=O)Nc2ccc(Cl)cc2C(=O)c2cc[n+]([O-])cc2)cc1
InChI	InChI=1S/C22H21ClN2O4S/c1-22(2,3)16-4-7-18(8-5-16)30(28,29)24-20-9-6-17(23)14-19(20)21(26)15-10-12-25(27)13-11-15/h4-14,24H,1-3H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H21ClN2O4S
Molecular Weight	444.94
AlogP	4.3
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	5.0
Polar Surface Area	90.18
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	30.0

Bioactivity

Mechanism of Action	Action	Reference
C-C chemokine receptor type 9 antagonist	ANTAGONIST	PubMed


Protein: C-C chemokine receptor type 9 Description: C-C chemokine receptor type 9 Organism : Homo sapiens P51686 ENSG00000173585

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CC chemokine receptor	-	3-539	-	1-10	-

Assay Description	Organism	Bioactivity	Reference
Antagonist activity at CCR9 assessed as inhibition of CCL25-induced chemotaxis by cell based assay	None	2.8 nM
Binding affinity to CCR9	None	6.0 nM
Antagonist activity at CCR9 receptor (unknown origin) assessed as inhibition of TECK-induced calcium mobilization incubated for 10 mins prior to TECK induction	Homo sapiens	10.0 nM
Antagonist activity at CCR9 receptor (unknown origin) by buffer chemotaxis assay	Homo sapiens	11.0 nM
Antagonist activity at CCR9 receptor (unknown origin) by serum chemotaxis assay	Homo sapiens	539.0 nM
Antagonist activity against CCR9 in human MOLT4 cells assessed as inhibition of human recombinant TECK-induced calcium response pre-treated before TECK stimulation by Flou-4-AM dye based FLIPR assay	Homo sapiens	100.0 nM
Antagonist activity against CCR9 in human MOLT4 cells assessed as inhibition of human recombinant TECK-induced cell migration pre-treated for 15 mins before TECK stimulation for 150 mins by fluorescence based assay	Homo sapiens	100.0 nM
Antagonist activity at CCR9 receptor in human MOLT4 cells assessed as inhibition of CCL25-induced increase in intracellular calcium level preincubated for 1 hr followed CCL25 addition by FLIPR assay	Homo sapiens	1.1 nM
Antagonist activity at CCR9A receptor (unknown origin) overexpressed in human MOLT4 cells assessed as inhibition of CCL25-induced increase in intracellular calcium level preincubated for 1 hr followed CCL25 addition by FLIPR assay	Homo sapiens	3.7 nM
Antagonist activity at CCR9 receptor in human MOLT4 cells assessed as inhibition of CCl25-mediated cell migration preincubated for 30 mins followed CCL25 addition incubated for 2 hrs by ChemoTx plate system	Homo sapiens	10.0 nM
Antagonist activity at CCR9 (unknown origin) assessed as inhibition of TECK-stimulated calcium mobilization preincubated for 10 mins followed by agonist addition measured for 90 sec by fluo-8 dye-based FLIPR assay	Homo sapiens	5.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-3.04 %
Antagonist activity at recombinant human CCR9A expressed in BAF3 cells assessed as reduction in CCL25-induced chemotaxis preincubated for 10 mins followed by addition of CCL25 and measured after 120 min by QUANT dye based fluorescence assay	Homo sapiens	2.8 nM
Antagonist activity at recombinant human CCR9B expressed in BAF3 cells assessed as reduction in CCL25-induced chemotaxis preincubated for 10 mins followed by addition of CCL25 and measured after 120 min by QUANT dye based fluorescence assay	Homo sapiens	2.6 nM
Inhibition of chemotaxis in mouse BAF3 cells	Mus musculus	2.8 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-1.384 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.11 %

Cross References

Resources	Reference
ChEMBL	CHEMBL2178578
DrugBank	DB15250
FDA SRS	MWI54OUA12
Guide to Pharmacology	9046
PDB	79K
PubChem	10343454
SureChEMBL	SCHEMBL342225
ZINC	ZINC000038562120

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).