tanshinone IIA   Click here for help

GtoPdb Ligand ID: 13771

Synonyms: salviol IIA | Tanshinone B
Compound class: Natural product
Comment: Tanshinone IIA is a plant-derived natural product. It has been reported in Salvia species. Extracts of Salvia miltiorrhiza roots are known as Danshen in traditional Chinese medicine. Tanshinone IIA is proposed as an active component of Danshen that presents a risk of adverse drug-drug interactions as it interferes with the metabolism of esterified (pro)drugs [1].
Click here for help

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.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 43.37
Molecular weight 294.35
XLogP 3.25
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
Click here for help

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/)

✖
Canonical SMILES CC1=COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
Isomeric SMILES CC1=COC2=C1C(=O)C(=O)C3=C2C=CC4=C3CCCC4(C)C
InChI InChI=1S/C19H18O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,9H,4-5,8H2,1-3H3
InChI Key HYXITZLLTYIPOF-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 Natural product
IUPAC Name Click here for help
1,6,6-trimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms Click here for help
salviol IIA | Tanshinone B
Database Links Click here for help
BindingDB Ligand 83922
CAS Registry No. 568-72-9 (source: PubChem)
ChEBI CHEBI:108595
ChEMBL Ligand CHEMBL187266
GtoPdb PubChem SID 507750404
PubChem CID 164676
Search Google for chemical match using the InChIKey HYXITZLLTYIPOF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HYXITZLLTYIPOF
UniChem Compound Search for chemical match using the InChIKey HYXITZLLTYIPOF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HYXITZLLTYIPOF-UHFFFAOYSA-N