tianeptine   Click here for help

GtoPdb Ligand ID: 7558

Synonyms: Stablon® | tianeptine sodium
Approved drug
tianeptine is an approved drug
Compound class: Synthetic organic
Comment: Chemically tianeptine can be classified as a tricyclic antidepressant (TCA), but evidence suggests that it has a quite different pharmacological mechanism of action compared to typical TCAs [2-4].
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 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 95.09
Molecular weight 436.12
XLogP 4.27
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 OC(=O)CCCCCCNC1c2ccccc2N(S(=O)(=O)c2c1ccc(c2)Cl)C
Isomeric SMILES OC(=O)CCCCCCNC1c2ccccc2N(S(=O)(=O)c2c1ccc(c2)Cl)C
InChI InChI=1S/C21H25ClN2O4S/c1-24-18-9-6-5-8-16(18)21(23-13-7-3-2-4-10-20(25)26)17-12-11-15(22)14-19(17)29(24,27)28/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26)
InChI Key JICJBGPOMZQUBB-UHFFFAOYSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
7-[(3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoic acid
International Nonproprietary Names Click here for help
INN number INN
4906 tianeptine
Synonyms Click here for help
Stablon® | tianeptine sodium
Database Links Click here for help
CAS Registry No. 66981-73-5
ChEMBL Ligand CHEMBL1289110
DrugCentral Ligand 2650
GtoPdb PubChem SID 223365894
PubChem CID 68870
Search Google for chemical match using the InChIKey JICJBGPOMZQUBB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JICJBGPOMZQUBB
Search PubMed clinical trials tianeptine
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Search PubMed titles/abstracts tianeptine
UniChem Compound Search for chemical match using the InChIKey JICJBGPOMZQUBB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JICJBGPOMZQUBB-UHFFFAOYSA-N
Wikipedia Tianeptine