PIBOSEROD

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Search structure


Synonyms	Piboserod SB-207266
Status
Molecule Category	UNKNOWN
UNII	4UQ3S81B25
EPA CompTox	DTXSID60165129


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

Structure


InChI Key	KVCSJPATKXABRQ-UHFFFAOYSA-N
Smiles	CCCCN1CCC(CNC(=O)c2c3n(c4ccccc24)CCCO3)CC1
InChI	InChI=1S/C22H31N3O2/c1-2-3-11-24-13-9-17(10-14-24)16-23-21(26)20-18-7-4-5-8-19(18)25-12-6-15-27-22(20)25/h4-5,7-8,17H,2-3,6,9-16H2,1H3,(H,23,26)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H31N3O2
Molecular Weight	369.51
AlogP	3.67
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	6.0
Polar Surface Area	46.5
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	27.0

Bioactivity

Mechanism of Action	Action	Reference
Serotonin 4 (5-HT4) receptor antagonist	ANTAGONIST	ClinicalTrials PubMed


Protein: Serotonin 4 (5-HT4) receptor Description: 5-hydroxytryptamine receptor 4 Organism : Homo sapiens Q13639 ENSG00000164270

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel	-	-	-	-	67
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor	-	1	-	0-2	73-97

Assay Description	Organism	Bioactivity	Reference
Binding affinity was determined against 5-hydroxytryptamine 3 receptor	Cavia porcellus	0.631 nM
Binding affinity was determined against 5-hydroxytryptamine 2C receptor using cloned rat receptors expressed in 293 cells radiolabeled with [3H]mesulergine	Cavia porcellus	0.5012 nM
Inhibitory constant for human cloned 5-HT4 receptor	Homo sapiens	0.2512 nM
Binding affinity at 5HT4 receptor	None	0.5012 nM
Displacement of [3H]GR113808 from human 5HT4 receptor expressed in HEK293 cells by liquid scintillation counting	Homo sapiens	0.05248 nM
Displacement of [3H](1-(2-(methylsulfonamido)ethyl)piperidin-4-yl)methyl 1-methyl-1H-indole-3-carboxylate from human 5HT4R expressed in HEK293 cells	Homo sapiens	0.1585 nM
Inhibition of human ERG at 1 uM	Homo sapiens	67.0 %
Displacement of [3H](1-(2-(methylsulfonamido)ethyl)piperidin-4-yl)methyl 1-methyl-1H-indole-3-carboxylate from human 5HT4R expressed in HEK293 cells at 1 nM	Homo sapiens	73.0 %
Displacement of [3H](1-(2-(methylsulfonamido)ethyl)piperidin-4-yl)methyl 1-methyl-1H-indole-3-carboxylate from human 5HT4R expressed in HEK293 cells at 10 nM	Homo sapiens	95.0 %
Displacement of [3H](1-(2-(methylsulfonamido)ethyl)piperidin-4-yl)methyl 1-methyl-1H-indole-3-carboxylate from human 5HT4R expressed in HEK293 cells at 0.1 uM	Homo sapiens	97.0 %
Displacement of [3H]GR113808 from human 5-HT4B receptor expressed in HEK293 cells after 1 hr by liquid scintillation counting analysis	Homo sapiens	0.1 nM
Displacement of [3H]GR113808 from human 5HT4B receptor expressed in HEK293 cells	Homo sapiens	0.1 nM
Displacement of [125I]SB207710 from 5-HT4 receptor in guinea pig brain membranes	Cavia porcellus	1.585 nM
Displacement of [125I]SB207710 from human recombinant 5-HT4 receptor	Homo sapiens	1.585 nM
Displacement of [3H]GR113808 from human 5HT4b receptor expressed in HEK293 cell membranes	Homo sapiens	0.3981 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	-5.28 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	3.084 %
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	-0.04 %		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	-0.04 %

Cross References

Resources	Reference
ChEMBL	CHEMBL356359
DrugBank	DB04873
FDA SRS	4UQ3S81B25
Guide to Pharmacology	225
PubChem	177336
SureChEMBL	SCHEMBL467339
ZINC	ZINC000001537633

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).