SLC-0111   Click here for help

GtoPdb Ligand ID: 10149

Synonyms: 4-fluorophenylureido-benzenesulfonamide | compound 7 [PMID: 21361354] | SLC0111
PDB Ligand
Compound class: Synthetic organic
Comment: SLC-0111 is a carbonic anhydrase (CA) IX/XII inhibitor that is being investigated for anti-neoplastic potential [1,4]. SLC-0111 is selective for the transmembrane CA isoforms IX and XII, compared to the cytosolic CA I and II isoforms. CA IX and XII are expressed predominantly in the hypoxic tumour microenvironment. Their inhibition promotes a significant antitumour/antimetastatic effect and reduces cancer stem cell numbers. The crystal structure of SLC-0111 bound to CA II has been resolved (see PDB ID 3N4B) [3].
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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

SLC-0111 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 6
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 109.67
Molecular weight 309.06
XLogP 1.1
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
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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 O=C(Nc1ccc(cc1)F)Nc1ccc(cc1)S(=O)(=O)N
Isomeric SMILES O=C(Nc1ccc(cc1)F)Nc1ccc(cc1)S(=O)(=O)N
InChI InChI=1S/C13H12FN3O3S/c14-9-1-3-10(4-2-9)16-13(18)17-11-5-7-12(8-6-11)21(15,19)20/h1-8H,(H2,15,19,20)(H2,16,17,18)
InChI Key YJQZNWPYLCNRLP-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/)
References
1. Carta F, Vullo D, Osman SM, AlOthman Z, Supuran CT. (2017)
Synthesis and carbonic anhydrase inhibition of a series of SLC-0111 analogs.
Bioorg Med Chem, 25 (9): 2569-2576. [PMID:28347633]
2. Congiu C, Onnis V, Deplano A, Balboni G, Dedeoglu N, Supuran CT. (2015)
Synthesis of sulfonamides incorporating piperazinyl-ureido moieties and their carbonic anhydrase I, II, IX and XII inhibitory activity.
Bioorg Med Chem Lett, 25 (18): 3850-3. [PMID:26233435]
3. Pacchiano F, Aggarwal M, Avvaru BS, Robbins AH, Scozzafava A, McKenna R, Supuran CT. (2010)
Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency.
Chem Commun (Camb.), 46 (44): 8371-3. [PMID:20922253]
4. Pacchiano F, Carta F, McDonald PC, Lou Y, Vullo D, Scozzafava A, Dedhar S, Supuran CT. (2011)
Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.
J Med Chem, 54 (6): 1896-902. [PMID:21361354]