DIDS   Click here for help

GtoPdb Ligand ID: 4177

Synonyms: 4,4'-diisothiocyanostilbene-2,2'-disulphonic acid | ABC inhibitor 2 [1]
Compound class: Synthetic organic
Comment: This compound inhibits ATP-binding cassette transporter 1 (ABCA1) [3].
There is some ambiguity as to the exact structure of this compund, with both the (E) and (Z) forms reported in the literature and on supplier websites. We show the (E) bond. The (Z) is shown in PubChem CID 9548709.
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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 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 8
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 214.4
Molecular weight 453.94
XLogP 4.3
No. Lipinski's rules broken 0
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 S=C=Nc1ccc(c(c1)S(=O)(=O)O)C=Cc1ccc(cc1S(=O)(=O)O)N=C=S
Isomeric SMILES S=C=Nc1ccc(c(c1)S(=O)(=O)O)C=Cc1ccc(cc1S(=O)(=O)O)N=C=S
InChI InChI=1S/C16H10N2O6S4/c19-27(20,21)15-7-13(17-9-25)5-3-11(15)1-2-12-4-6-14(18-10-26)8-16(12)28(22,23)24/h1-8H,(H,19,20,21)(H,22,23,24)
InChI Key YSCNMFDFYJUPEF-UHFFFAOYSA-N
Bioactivity Comments
DIDS dose-dependently inhibits the ABCA1-specific anion efflux when the transporter is expressed in Xenopus oocytes [2]. DIDS also dose-dependently, and selectively inhibits inhibit IL-1β secretion, indicating a pharmacological relationship between ABCA1, IL-1β [3] and modulation of the inflammasome [1].
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
ClC-7 Hs Channel blocker - 4.4 pIC50 - 4
⤷ pIC50 4.4 (IC50 4x10-5 M) [4]
Maxi Cl- Hs Channel blocker - 4.4 pIC50 - 4
⤷ pIC50 4.4 (IC50 4x10-5 M) [4]
ClC-6 Hs Channel blocker - 3.0 pIC50 -
⤷ pIC50 3.0 (IC50 1x10-3 M)
ClC-Ka Hs Channel blocker - - - -
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ClC-Kb Hs Channel blocker - - - -
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CaCC Hs Channel blocker - - - -
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VRAC Hs Channel blocker - - - -
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Targets where the ligand is described in the comment field
Target Comment
ClC-3 insensitive to the channel blockers DIDS, NPPB and tamoxifen (10 μM)
ClC-5 Insensitive to the channel blockers DIDS (1 mM), diphenylamine-2-carboxylic acid (1 mM), 9-anthroic acid (2 mM), NPPB (0.5 mM) and niflumic acid (1 mM)
Ligand mentioned in the following text fields
Calcium activated chloride channel (CaCC) comments
ClC family comments
Maxi chloride channel comments
SLC39 family of metal ion transporters comments
Vesicular nucleotide transporter comments