TERUTROBAN

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Search structure


Synonyms	S18886 Terutroban Triplion
Status
Molecule Category	UNKNOWN
UNII	A6WX9391D8


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

Structure


InChI Key	HWEOXFSBSQIWSY-MRXNPFEDSA-N
Smiles	Cc1ccc2c(c1CCC(=O)O)CC[C@@H](NS(=O)(=O)c1ccc(Cl)cc1)C2
InChI	InChI=1S/C20H22ClNO4S/c1-13-2-3-14-12-16(6-9-19(14)18(13)10-11-20(23)24)22-27(25,26)17-7-4-15(21)5-8-17/h2-5,7-8,16,22H,6,9-12H2,1H3,(H,23,24)/t16-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H22ClNO4S
Molecular Weight	407.92
AlogP	3.5
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	6.0
Polar Surface Area	83.47
Molecular species	ACID
Aromatic Rings	2.0
Heavy Atoms	27.0

Bioactivity

Mechanism of Action	Action	Reference
Thromboxane A2 receptor antagonist	ANTAGONIST	PubMed Wikipedia


Protein: Thromboxane A2 receptor Description: Thromboxane A2 receptor Organism : Homo sapiens P21731 ENSG00000006638

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Prostanoid receptor	-	16	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antagonist activity against human thromboxane A2 receptor alpha expressed in QBI-HEK293A cells assessed as reduction in I-BOP-induced inositol monophosphate production incubated for 15 to 60 mins before I-BOP addition by HTRF assay	Homo sapiens	16.4 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	5.7 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	2.655 %
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	-0.15 %		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	-0.15 %

Cross References

Resources	Reference
ChEMBL	CHEMBL2107786
FDA SRS	A6WX9391D8
Guide to Pharmacology	6073
PubChem	9938840
SureChEMBL	SCHEMBL1896773
ZINC	ZINC000003811419

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).