ICILLIN

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Search structure


Synonyms	Icilin Icillin
Status
Molecule Category	UNKNOWN
UNII	CS70PZQ4QJ
EPA CompTox	DTXSID70190442


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

Structure


InChI Key	RCEFMOGVOYEGJN-UHFFFAOYSA-N
Smiles	O=C1NC(c2cccc([N+](=O)[O-])c2)=CCN1c1ccccc1O
InChI	InChI=1S/C16H13N3O4/c20-15-7-2-1-6-14(15)18-9-8-13(17-16(18)21)11-4-3-5-12(10-11)19(22)23/h1-8,10,20H,9H2,(H,17,21)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H13N3O4
Molecular Weight	311.3
AlogP	2.87
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	3.0
Polar Surface Area	95.71
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	23.0

Assay Description	Organism	Bioactivity	Reference
Agonist activity at rat recombinant TRPM8 receptor expressed in HEK293 cells assessed as increase in intracellular calcium concentration by fluorimetric test	Rattus norvegicus	190.0 nM
Activation of TRPM8 channel	None	60.0 nM
Inhibition of human TRPM8 (unknown origin) expressed in HEK293 cells assessed as inhibition of WS12-induced Ca2+ elevation by FLIPR assay	Homo sapiens	300.0 nM
Agonist activity at rat TRPM8 expressed in HEK293 cells assessed as induction of intracellular Ca2+ level by Fluo-4-AM dye based spectrofluorimetry	Rattus norvegicus	110.0 nM
Antagonist activity against rat TRPM8 expressed in HEK293 cells assessed as inhibition of icilin-induced intracellular Ca2+ level pre-treated 5 mins before icilin stimulation by Fluo-4-AM dye based spectrofluorimetry	Rattus norvegicus	58.0 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	55.13 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	11.83 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-1.476 %
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	-0.08 %		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	0.0 %		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	0.0 %		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	-0.08 %

Cross References

Resources	Reference
ChEBI	92845
ChEMBL	CHEMBL258405
FDA SRS	CS70PZQ4QJ
Guide to Pharmacology	2429
PDB	KX7
SureChEMBL	SCHEMBL663503
ZINC	ZINC000000620751

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).