benzatropine   Click here for help

GtoPdb Ligand ID: 7601

Synonyms: benztropine | benztropine mesylate | Cogentin®
Approved drug PDB Ligand
benzatropine is an approved drug (FDA (1954))
Compound class: Synthetic organic
Comment: Benzatropine (benztropine) is an anticholinergic drug. PubChem CID 1201549 represents an alternative isomer of this compound.
Benzatropine is reported as an inhibitor of the neutral amino acid transporter B0AT1 (SLC6A19) [1], a recently identified molecular target for treatment of type 2 diabetes and related disorders [2]. Note that the mesylate salt was used in the experiments reported in [1]. B0AT1 has been identified as a potential ancillary protein for SARS-CoV-2 entry into host cells. Benzatropine was reported to inhibit SARS-CoV-2 infection in vitro [4].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 12.47
Molecular weight 307.19
XLogP 4.28
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1C2CCC1CC(C2)OC(c1ccccc1)c1ccccc1
Isomeric SMILES CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(c1ccccc1)c1ccccc1
InChI InChI=1S/C21H25NO/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-21H,12-15H2,1H3/t18-,19+,20+
InChI Key GIJXKZJWITVLHI-PMOLBWCYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Cheng Q, Shah N, Bröer A, Fairweather S, Jiang Y, Schmoll D, Corry B, Bröer S. (2017)
Identification of novel inhibitors of the amino acid transporter B0 AT1 (SLC6A19), a potential target to induce protein restriction and to treat type 2 diabetes.
Br J Pharmacol, 174 (6): 468-482. [PMID:28176326]
2. Jiang Y, Rose AJ, Sijmonsma TP, Bröer A, Pfenninger A, Herzig S, Schmoll D, Bröer S. (2015)
Mice lacking neutral amino acid transporter B(0)AT1 (Slc6a19) have elevated levels of FGF21 and GLP-1 and improved glycaemic control.
Mol Metab, 4 (5): 406-17. [PMID:25973388]
3. Newman AH, Kline RH, Allen AC, Izenwasser S, George C, Katz JL. (1995)
Novel 4'-substituted and 4',4"-disubstituted 3 alpha-(diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors.
J Med Chem, 38 (20): 3933-40. [PMID:7562926]
4. Williams TL, Colzani MT, Macrae RGC, Robinson EL, Bloor S, Greenwood EJD, Zhan JR, Strachan G, Kuc RE, Nyimanu D et al.. (2021)
Human embryonic stem cell-derived cardiomyocyte platform screens inhibitors of SARS-CoV-2 infection.
Commun Biol, 4 (1): 926. [PMID:34326460]