Target Binding Site Detail
| Target General Information | Top | ||||
|---|---|---|---|---|---|
| Target ID | T20401 | Target Info | |||
| Target Name | Carbonic anhydrase II (CA-II) | ||||
| Synonyms | Carbonic anhydrase C; Carbonic anhydrase 2; Carbonate dehydratase II; CAC | ||||
| Target Type | Successful Target | ||||
| Gene Name | CA2 | ||||
| Biochemical Class | Alpha-carbonic anhydrase | ||||
| UniProt ID | |||||
| Ligand General Information | Top | ||||
|---|---|---|---|---|---|
| Ligand Name | Benzenesulfonamide | Ligand Info | |||
| Canonical SMILES | C1=CC=C(C=C1)S(=O)(=O)N | ||||
| InChI | 1S/C6H7NO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9) | ||||
| InChIKey | KHBQMWCZKVMBLN-UHFFFAOYSA-N | ||||
| PubChem Compound ID | 7370 | ||||
| Drug Binding Sites of Target | Top | |||||
|---|---|---|---|---|---|---|
| PDB ID: 4YX4 Human Carbonic Anhydrase II complexed with an inhibitor with a benzenesulfonamide group (1). | ||||||
| Method | X-ray diffraction | Resolution | 1.01 Å | Mutation | No | [1] |
| PDB Sequence |
HWGYGKHNGP
13 EHWHKDFPIA23 KGERQSPVDI33 DTHTAKYDPS43 LKPLSVSYDQ53 ATSLRILNNG 63 HAFNVEFDDS73 QDKAVLKGGP83 LDGTYRLIQF93 HFHWGSLDGQ103 GSEHTVDKKK 113 YAAELHLVHW123 NTKYGDFGKA134 VQQPDGLAVL144 GIFLKVGSAK154 PGLQKVVDVL 164 DSIKTKGKSA174 DFTNFDPRGL184 LPESLDYWTY194 PGSLTTPPLL204 ECVTWIVLKE 214 PISVSSEQVL224 KFRKLNFNGE234 GEPEELMVDN244 WRPAQPLKNR254 QIKASFK |
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| PDB ID: 4JSA Benzenesulfonamide complexed with hCAII H94D | ||||||
| Method | X-ray diffraction | Resolution | 1.50 Å | Mutation | Yes | [2] |
| PDB Sequence |
HWGYGKHNGP
13 EHWHKDFPIA23 KGERQSPVDI33 DTHTAKYDPS43 LKPLSVSYDQ53 ATSLRILNNG 63 HAFNVEFDDS73 QDKAVLKGGP83 LDGTYRLIQF93 DFHWGSLDGQ103 GSEHTVDKKK 113 YAAELHLVHW123 NTKYGDFGKA134 VQQPDGLAVL144 GIFLKVGSAK154 PGLQKVVDVL 164 DSIKTKGKSA174 DFTNFDPRGL184 LPESLDYWTY194 PGSLTTPPLL204 ECVTWIVLKE 214 PISVSSEQVL224 KFRKLNFNGE234 GEPEELMVDN244 WRPAQPLKNR254 QIKASFK |
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HIS4
3.899
TRP5
3.602
HIS10
3.623
ASN11
3.482
GLY12
4.473
HIS15
2.909
TRP16
3.375
HIS17
4.887
LYS18
4.167
ASP19
2.759
PHE20
3.794
GLN92
3.967
|
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| PDB ID: 4JSZ Benzenesulfonamide bound to hCAII H94C | ||||||
| Method | X-ray diffraction | Resolution | 1.90 Å | Mutation | Yes | [2] |
| PDB Sequence |
HWGYGKHNGP
13 EHWHKDFPIA23 KGERQSPVDI33 DTHTAKYDPS43 LKPLSVSYDQ53 ATSLRILNNG 63 HAFNVEFDDS73 QDKAVLKGGP83 LDGTYRLIQF93 CFHWGSLDGQ103 GSEHTVDKKK 113 YAAELHLVHW123 NTKYGDFGKA134 VQQPDGLAVL144 GIFLKVGSAK154 PGLQKVVDVL 164 DSIKTKGKSA174 DFTNFDPRGL184 LPESLDYWTY194 PGSLTTPPLL204 ECVTWIVLKE 214 PISVSSEQVL224 KFRKLNFNGE234 GEPEELMVDN244 WRPAQPLKNR254 QIKASFK |
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HIS4
3.821
TRP5
3.529
GLY6
4.854
HIS10
3.545
ASN11
3.517
GLY12
4.481
HIS15
2.786
TRP16
3.352
HIS17
4.866
LYS18
4.157
ASP19
2.985
PHE20
3.796
GLN92
3.762
|
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| PDB ID: 2WEJ Thermodynamic Optimisation of Carbonic Anhydrase Fragment Inhibitors | ||||||
| Method | X-ray diffraction | Resolution | 1.45 Å | Mutation | No | [3] |
| PDB Sequence |
HHWGYGKHNG
12 PEHWHKDFPI22 AKGERQSPVD32 IDTHTAKYDP42 SLKPLSVSYD52 QATSLRILNN 62 GHAFNVEFDD72 SQDKAVLKGG82 PLDGTYRLIQ92 FHFHWGSLDG102 QGSEHTVDKK 112 KYAAELHLVH122 WNTKYGDFGK133 AVQQPDGLAV143 LGIFLKVGSA153 KPGLQKVVDV 163 LDSIKTKGKS173 ADFTNFDPRG183 LLPESLDYWT193 YPGSLTTPPL203 LECVTWIVLK 213 EPISVSSEQV223 LKFRKLNFNG233 EGEPEELMVD243 NWRPAQPLKN253 RQIKASFK |
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Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .FB2 or .FB22 or .FB23 or :3FB2;style chemicals stick;color identity;select .A:92 or .A:94 or .A:96 or .A:106 or .A:119 or .A:121 or .A:131 or .A:141 or .A:143 or .A:197 or .A:198 or .A:199 or .A:200 or .A:209; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
|
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| PDB ID: 5NYA Carbonic Anhydrase II Inhibitor RA13 | ||||||
| Method | X-ray diffraction | Resolution | 1.20 Å | Mutation | No | [4] |
| PDB Sequence |
HWGYGKHNGP
13 EHWHKDFPIA23 KGERQSPVDI33 DTHTAKYDPS43 LKPLSVSYDQ53 ATSLRILNNG 63 HAFNVEFDDS73 QDKAVLKGGP83 LDGTYRLIQF93 HFHWGSLDGQ103 GSEHTVDKKK 113 YAAELHLVHW123 NTKYGDFGKA134 VQQPDGLAVL144 GIFLKVGSAK154 PGLQKVVDVL 164 DSIKTKGKSA174 DFTNFDPRGL184 LPESLDYWTY194 PGSLTTPPLL204 ECVTWIVLKE 214 PISVSSEQVL224 KFRKLNFNGE234 GEPEELMVDN244 WRPAQPLKNR254 QIKASFK |
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|
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .FB2 or .FB22 or .FB23 or :3FB2;style chemicals stick;color identity;select .A:92 or .A:94 or .A:96 or .A:106 or .A:119 or .A:121 or .A:131 or .A:141 or .A:143 or .A:197 or .A:198 or .A:199 or .A:200 or .A:209; color #00ffc7; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
|
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| PDB ID: 6GDC Human Carbonic Anhydrase II in complex with Benzenesulfonamide | ||||||
| Method | X-ray diffraction | Resolution | 1.08 Å | Mutation | No | [5] |
| PDB Sequence |
HWGYGKHNGP
13 EHWHKDFPIA23 KGERQSPVDI33 DTHTAKYDPS43 LKPLSVSYDQ53 ATSLRILNNG 63 HAFNVEFDDS73 QDKAVLKGGP83 LDGTYRLIQF93 HFHWGSLDGQ103 GSEHTVDKKK 113 YAAELHLVHW123 NTKYGDFGKA134 VQQPDGLAVL144 GIFLKVGSAK154 PGLQKVVDVL 164 DSIKTKGKSA174 DFTNFDPRGL184 LPESLDYWTY194 PGSLTTPPLL204 ECVTWIVLKE 214 PISVSSEQVL224 KFRKLNFNGE234 GEPEELMVDN244 WRPAQPLKNR254 QIKASFK |
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|
Click to Show 3D Structure of This Binding Site
set background white;style ions nothing; color 8e8e8e;style chemicals nothing; select .FB2 or .FB22 or .FB23 or :3FB2;style chemicals stick;color identity;select .A:4 or .A:5 or .A:6 or .A:10 or .A:11 or .A:12 or .A:15 or .A:16 or .A:17 or .A:18 or .A:19 or .A:20 or .A:92 or .A:94 or .A:96 or .A:106 or .A:119 or .A:121 or .A:131 or .A:141 or .A:143 or .A:197 or .A:198 or .A:199 or .A:200 or .A:202 or .A:207 or .A:209; color #f3c393; zoom selection;set surface opacity 0.5;set surface Van der Waals surface;set mode all
|
HIS4
3.610
TRP5
2.794
GLY6
4.243
HIS10
4.151
ASN11
3.461
GLY12
4.751
HIS15
2.904
TRP16
2.437
HIS17
4.831
LYS18
2.509
ASP19
2.386
PHE20
3.201
GLN92
3.534
HIS94
2.678
|
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| References | Top | ||||
|---|---|---|---|---|---|
| REF 1 | Kinetic and Structural Insights into the Mechanism of Binding of Sulfonamides to Human Carbonic Anhydrase by Computational and Experimental Studies. J Med Chem. 2016 May 12;59(9):4245-56. | ||||
| REF 2 | Metalloprotein-inhibitor binding: human carbonic anhydrase II as a model for probing metal-ligand interactions in a metalloprotein active site. Inorg Chem. 2013 Nov 4;52(21):12207-15. | ||||
| REF 3 | Thermodynamic optimisation in drug discovery: a case study using carbonic anhydrase inhibitors. ChemMedChem. 2009 Dec;4(12):1985-9. | ||||
| REF 4 | Ranking Power of the SQM/COSMO Scoring Function on Carbonic Anhydrase?II-Inhibitor Complexes. Chemphyschem. 2018 Apr 5;19(7):873-879. | ||||
| REF 5 | Conformational Changes in Alkyl Chains Determine the Thermodynamic and Kinetic Binding Profiles of Carbonic Anhydrase Inhibitors. ACS Chem Biol. 2020 Mar 20;15(3):675-685. | ||||
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