tetrandrine   Click here for help

GtoPdb Ligand ID: 11859

Synonyms: (+)-Tetrandrine | (S,S)-Tetrandrine | D-Tetrandrine | fanchinin | Tetrandrin
Approved drug
tetrandrine is an approved drug (China)
Compound class: Synthetic organic
Comment: Tetrandrine is a compound that can be extracted from the Stephania tetrandra vine, or synthesised chemically. It has been demonstrated to act as an inhibitor of multiple ion channels, including two-pore channels 1 and 2 (TPC1/2), and L- and T-type calcium channels [2-3]. The TPC calcium channels appear to be important for Ebola virus infection of host cells, and in vitro either ablation of TPC expression or tetrandrine-mediated inhibition of TPC channels reduces Ebola infection (IC50 55 nM) [3].

SARS-CoV-2 infection (COVID-19): Tetrandrine is being studied in clinical trial for potential to treat COVID-19. The biological and pharmacological rationale for this use was reviewed in [1].
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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

tetrandrine is commercially available from our sponsors

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 61.86
Molecular weight 622.3
XLogP 5.49
No. Lipinski's rules broken 1

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 COc1c(OC)cc2c3c1Oc1cc4c(cc1OC)CCN([C@H]4Cc1ccc(Oc4cc(C[C@@H]3N(CC2)C)ccc4OC)cc1)C
Isomeric SMILES CN1CCc2cc(c3cc2[C@@H]1Cc1ccc(cc1)Oc1c(ccc(c1)C[C@H]1c2c(O3)c(c(cc2CCN1C)OC)OC)OC)OC
InChI InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30-/m0/s1
InChI Key WVTKBKWTSCPRNU-KYJUHHDHSA-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. China (0)
International Nonproprietary Names Click here for help
INN number INN
13497 tetrandrine
Synonyms Click here for help
(+)-Tetrandrine | (S,S)-Tetrandrine | D-Tetrandrine | fanchinin | Tetrandrin
Database Links Click here for help
BindingDB Ligand 50478473
CAS Registry No. 518-34-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL176045
GtoPdb PubChem SID 461663415
PubChem CID 73078
Search Google for chemical match using the InChIKey WVTKBKWTSCPRNU-KYJUHHDHSA-N
Search Google for chemicals with the same backbone WVTKBKWTSCPRNU
Search PubMed clinical trials tetrandrine
Search PubMed titles tetrandrine
Search PubMed titles/abstracts tetrandrine
UniChem Compound Search for chemical match using the InChIKey WVTKBKWTSCPRNU-KYJUHHDHSA-N
UniChem Connectivity Search for chemical match using the InChIKey WVTKBKWTSCPRNU-KYJUHHDHSA-N

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MedChemExpress
Tetrandrine (links to external site)
Cat. No. HY-13764