GTS-21

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Search structure


Synonyms	3-(2,4-Dimethoxybenzylidene)Anabaseine Dimethoxybenzylidene anabaseine Dmxb-a Gts-21
Status
Molecule Category	UNKNOWN
UNII	8S399XDN2K


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

Structure


InChI Key	RPYWXZCFYPVCNQ-RVDMUPIBSA-N
Smiles	COc1ccc(/C=C2\CCCN=C2c2cccnc2)c(OC)c1
InChI	InChI=1S/C19H20N2O2/c1-22-17-8-7-14(18(12-17)23-2)11-15-5-4-10-21-19(15)16-6-3-9-20-13-16/h3,6-9,11-13H,4-5,10H2,1-2H3/b15-11+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H20N2O2
Molecular Weight	308.38
AlogP	3.77
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	4.0
Polar Surface Area	43.71
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	23.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of [125I]alpha-bungarotoxin binding to rat nicotinic acetylcholine receptor alpha7	Rattus norvegicus	220.0 nM
Inhibition of [3H]cytisine binding to nicotinic acetylcholine receptor alpha4-beta2 from rat cerebral cortex	Rattus norvegicus	84.0 nM
Displacement of [125I]alpha-bungarotoxin from alpha7 nAChR	None	158.0 nM
Displacement of [125I]-alpha-bungarotoxin from alpha7 nAChR in rat brain membrane after 3 hrs	Rattus norvegicus	130.0 nM
Displacement of [3H]cytisine from alpha4beta2 nAChR in rat brain membrane after 3 hrs	Rattus norvegicus	250.0 nM
Displacement of [3H]-epibatidine from Lymnaea stagnalis N-terminal FLAG-tagged AChBP expressed in HEK293 cells after 2 hrs by liquid scintillation counting	Lymnaea stagnalis	19.0 nM
Displacement of [3H]-epibatidine from Aplysia californica N-terminal FLAG-tagged AChBP expressed in HEK293 cells after 2 hrs by liquid scintillation counting	Aplysia californica	330.0 nM
Displacement of [3H]-epibatidine from Bulinus truncatus N-terminal FLAG-tagged AChBP F149L mutant expressed in HEK293 cells after 2 hrs by liquid scintillation counting	Bulinus truncatus	59.0 nM
Displacement of [3H]-epibatidine from alpha4beta2 nAChR in rat cortical membranes after 2 hrs by liquid scintillation counting	Rattus norvegicus	51.0 nM
Displacement of [3H]epibatidine from human alpha4beta2 nAchR expressed in SH-EP1 cells	Homo sapiens	51.0 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	-6.68 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	12.79 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	20.55 %
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	-0.17 %		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	-0.12 %		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	-0.17 %		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	-0.12 %

Cross References

Resources	Reference
ChEMBL	CHEMBL134713
DrugBank	DB05708
FDA SRS	8S399XDN2K
PDB	ZY7
PubChem	5310985
SureChEMBL	SCHEMBL316745
ZINC	ZINC000000000860

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).