Target Binding Site Detail

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Target General Information
Ligand General Information
Drug Binding Sites of Target
References
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
CAH2_HUMAN
Ligand General Information  Top
Ligand Name 2,3,6-Trifluoro-5-{[(1r,2s)-2-Hydroxy-1,2-Diphenylethyl]amino}-4-[(2-Hydroxyethyl)sulfonyl]benzenesulfonamide Ligand Info
Canonical SMILES C1=CC=C(C=C1)C(C(C2=CC=CC=C2)O)NC3=C(C(=C(C(=C3S(=O)(=O)CCO)F)F)S(=O)(=O)N)F
InChI 1S/C22H21F3N2O6S2/c23-15-16(24)22(34(30,31)12-11-28)19(17(25)21(15)35(26,32)33)27-18(13-7-3-1-4-8-13)20(29)14-9-5-2-6-10-14/h1-10,18,20,27-29H,11-12H2,(H2,26,32,33)/t18-,20+/m1/s1
InChIKey ZOZJONWJZVJBCD-QUCCMNQESA-N
PubChem Compound ID 91667929
Drug Binding Sites of Target  Top
PDB ID: 4QIY      Crystal structure of human carbonic anhydrase isozyme II with inhibitor
Method X-ray diffraction Resolution 1.30 Å Mutation No [1]
PDB Sequence
HWGYGKHNGP
13
EHWHKDFPIA
23
KGERQSPVDI
33
DTHTAKYDPS
43
LKPLSVSYDQ
53

ATSLRILNNG
63
HAFNVEFDDS
73
QDKAVLKGGP
83
LDGTYRLIQF
93
HFHWGSLDGQ
103

GSEHTVDKKK
113
YAAELHLVHW
123
NTKYGDFGKA
134
VQQPDGLAVL
144
GIFLKVGSAK
154

PGLQKVVDVL
164
DSIKTKGKSA
174
DFTNFDPRGL
184
LPESLDYWTY
194
PGSLTTPPLL
204

ECVTWIVLKE
214
PISVSSEQVL
224
KFRKLNFNGE
234
GEPEELMVDN
244
WRPAQPLKNR
254

QIKASFK
Residue
Distance (Å)
TRP5
4.068
TYR7
4.888
ASN62
3.095
HIS64
4.150
ALA65
4.314
PHE66
4.811
ASN67
2.154
ILE91
3.742
GLN92
3.388
HIS94
3.178
HIS96
2.919
GLU106
3.969
HIS119
3.301
Residue
Distance (Å)
VAL121
3.783
PHE131
3.645
VAL135
3.805
LEU141
3.800
VAL143
4.103
SER197
4.435
LEU198
3.065
THR199
2.759
THR200
3.142
PRO201
4.515
PRO202
3.557
LEU204
4.407
TRP209
4.429
PDB ID: 6YH9      Crystal structure of chimeric carbonic anhydrase XII with 2,3,6-trifluoro-5-{[(1R,2S)-2-hydroxy-1,2-diphenylethyl]amino}-4-[(2-hydroxyethyl)sulfonyl]benzenesulfonamide
Method X-ray diffraction Resolution 1.55 Å Mutation Yes [2]
PDB Sequence
HWGYGKHNGP
13
EHWHKDFPIA
23
KGERQSPVDI
33
DTHTAKYDPS
43
LKPLSVSYDQ
53

ATSLRILNNG
63
HSFKVEFDDS
73
QDKAVLKGGP
83
LDGTYRLTQF
93
HFHWGSLDGQ
103

GSEHTVDKKK
113
YAAELHLVHW
123
NTKYGDAGKA
134
SQQPDGLAVL
144
GIFLKVGSAK
154

PGLQKVVDVL
164
DSIKTKGKSA
174
DFTNFDPRGL
184
LPESLDYWTY
194
PGSLTTPPLN
204

ECVTWIVLKE
214
PISVSSEQVL
224
KFRKLNFNGE
234
GEPEELMVDN
244
WRPAQPLKNR
254

QIKASFK
Residue
Distance (Å)
TRP5
3.884
TYR7
4.974
ASN62
2.888
HIS64
4.233
SER65
4.232
LYS67
4.079
THR91
3.603
GLN92
3.587
HIS94
3.068
HIS96
2.891
GLU106
3.601
HIS119
3.175
VAL121
3.712
Residue
Distance (Å)
ALA131
3.608
GLY132
4.491
SER135
3.268
LEU141
3.548
VAL143
4.028
SER197
4.392
LEU198
3.037
THR199
2.437
THR200
3.301
PRO201
4.222
PRO202
3.685
ASN204
4.285
TRP209
4.389
References  Top
REF 1 Functionalization of fluorinated benzenesulfonamides and their inhibitory properties toward carbonic anhydrases. ChemMedChem. 2015 Apr;10(4):662-87.
REF 2 Switching the Inhibitor-Enzyme Recognition Profile via Chimeric Carbonic Anhydrase XII. ChemistryOpen. 2021 May;10(5):567-580.

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