tetrandrine   Click here for help

GtoPdb Ligand ID: 11859

Synonyms: (+)-Tetrandrine | (S,S)-Tetrandrine | D-Tetrandrine | 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].
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 CDK toolkit. 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
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.

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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (China)
Synonyms Click here for help
(+)-Tetrandrine | (S,S)-Tetrandrine | D-Tetrandrine | Tetrandrin
Database Links Click here for help
CAS Registry No. 518-34-3 (source: PubChem)
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
UniChem Compound Search for chemical match using the InChIKey WVTKBKWTSCPRNU-KYJUHHDHSA-N
UniChem Connectivity Search for chemical match using the InChIKey WVTKBKWTSCPRNU-KYJUHHDHSA-N