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.
2D Structure
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Physico-chemical Properties
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
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)
1. Baldwin AG, Brough D, Freeman S. (2016)
Inhibiting the Inflammasome: A Chemical Perspective.
J. Med. Chem., 59 (5): 1691-710. [PMID:26422006]
2. Becq F, Hamon Y, Bajetto A, Gola M, Verrier B, Chimini G. (1997)
ABC1, an ATP binding cassette transporter required for phagocytosis of apoptotic cells, generates a regulated anion flux after expression in Xenopus laevis oocytes.
J. Biol. Chem., 272 (5): 2695-9. [PMID:9006906]
3. Hamon Y, Luciani MF, Becq F, Verrier B, Rubartelli A, Chimini G. (1997)
Interleukin-1beta secretion is impaired by inhibitors of the Atp binding cassette transporter, ABC1.
Blood, 90 (8): 2911-5. [PMID:9376570]
4. Schulz P, Werner J, Stauber T, Henriksen K, Fendler K. (2010)
The G215R mutation in the Cl-/H+-antiporter ClC-7 found in ADO II osteopetrosis does not abolish function but causes a severe trafficking defect.
PLoS ONE, 5 (9): e12585. [PMID:20830208]