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 N-(2-{[(furan-2-yl)methyl][2-(4-sulfamoylphenyl)ethyl]amino}-2-oxoethyl)-N-(2-phenylethyl)-beta-alanine Ligand Info
Canonical SMILES C1=CC=C(C=C1)CCN(CCC(=O)O)CC(=O)N(CCC2=CC=C(C=C2)S(=O)(=O)N)CC3=CC=CO3
InChI 1S/C26H31N3O6S/c27-36(33,34)24-10-8-22(9-11-24)13-17-29(19-23-7-4-18-35-23)25(30)20-28(16-14-26(31)32)15-12-21-5-2-1-3-6-21/h1-11,18H,12-17,19-20H2,(H,31,32)(H2,27,33,34)
InChIKey VOLPYGCWCBVKEI-UHFFFAOYSA-N
PubChem Compound ID 146171282
Drug Binding Sites of Target  Top
PDB ID: 6WQ8      Carbonic Anhydrase II Complexed with 3-((2-((Furan-2-ylmethyl)(4-sulfamoylphenethyl)amino)-2-oxoethyl)(phenethyl)amino)propanoic acid
Method X-ray diffraction Resolution 1.41 Å Mutation No [1]
PDB Sequence
HHWGYGKHNG
12
PEHWHKDFPI
22
AKGERQSPVD
32
IDTHTAKYDP
42
SLKPLSVSYD
52

QATSLRILNN
62
GHAFNVEFDD
72
SQDKAVLKGG
82
PLDGTYRLIQ
92
FHFHWGSLDG
102

QGSEHTVDKK
112
KYAAELHLVH
122
WNTKYGDFGK
133
AVQQPDGLAV
143
LGIFLKVGSA
153

KPGLQKVVDV
163
LDSIKTKGKS
173
ADFTNFDPRG
183
LLPESLDYWT
193
YPGSLTTPPL
203

LECVTWIVLK
213
EPISVSSEQV
223
LKFRKLNFNG
233
EGEPEELMVD
243
NWRPAQPLKN
253

RQIKASFK
Residue
Distance (Å)
HIS3
4.399
HIS4
1.548
TRP5
2.064
GLY6
4.533
GLY8
4.205
HIS10
2.631
ASN11
1.923
GLY12
4.634
HIS15
2.425
TRP16
2.350
HIS17
4.845
LYS18
3.255
ASP19
2.725
PHE20
1.957
ARG58
4.505
LEU60
3.573
ASN67
3.933
GLU69
4.316
ILE91
3.149
GLN92
3.004
HIS94
2.657
Residue
Distance (Å)
HIS96
2.980
GLU106
3.396
HIS119
3.151
VAL121
2.333
ASP130
2.860
PHE131
2.409
GLY132
2.560
LYS133
4.744
VAL135
2.481
LEU141
4.669
VAL143
2.956
SER197
4.095
LEU198
2.456
THR199
2.013
THR200
2.498
PRO201
3.984
PRO202
2.882
LEU204
2.620
VAL207
4.237
TRP209
2.886
PDB ID: 7SUW      Carbonic Anhydrase IX-mimic with 2-((3-Aminopropyl)(phenethyl)amino)-N-(furan-2-ylmethyl)-N-(4-sulfamoylphenethyl)acetamide
Method X-ray diffraction Resolution 1.46 Å Mutation Yes [2]
PDB Sequence
HWGYGKHNGP
13
EHWHKDFPIA
23
KGERQSPVDI
33
DTHTAKYDPS
43
LKPLSVSYDQ
53

ATSLRILNNG
63
HSFQVTFDDS
73
QDKAVLKGGP
83
LDGTYRLLQF
93
HFHWGSLDGQ
103

GSEHTVDKKK
113
YAAELHLVHW
123
NTKYGDVGKA
134
VQQPDGLAVL
144
GIFLKVGSAK
154

PGLQKVVDVL
164
DSIKTEGKSA
174
DFTNFDPRGL
184
LPESLDYWTY
194
PGSLTTPPLA
204

ECVTWIVLKE
214
PISVSSEQVL
224
KFRKLNFNGE
234
GEPEELMVDN
244
WRPAQPLKNR
254

QIKASFK
Residue
Distance (Å)
GLN67
3.657
THR69
4.463
LEU91
2.155
GLN92
3.148
HIS94
2.663
HIS96
3.010
GLU106
3.358
HIS119
3.024
VAL121
2.409
ASP130
4.197
VAL131
2.035
GLY132
2.848
Residue
Distance (Å)
VAL135
2.853
GLN136
4.898
LEU141
3.325
VAL143
2.828
SER197
4.024
LEU198
2.544
THR199
2.103
THR200
2.335
PRO201
4.186
PRO202
3.074
VAL207
4.255
TRP209
2.671
References  Top
REF 1 Sulfonamide Inhibitors of Human Carbonic Anhydrases Designed through a Three-Tails Approach: Improving Ligand/Isoform Matching and Selectivity of Action. J Med Chem. 2020 Jul 9;63(13):7422-7444.
REF 2 The three-tails approach as a new strategy to improve selectivity of action of sulphonamide inhibitors against tumour-associated carbonic anhydrase IX and XII. J Enzyme Inhib Med Chem. 2022 Dec;37(1):930-939.

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