Structure of PDB 2irw Chain C Binding Site BS02

Receptor Information
>2irw Chain C (length=257) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
EFRPEMLQGKKVIVTGASKGIGREMAYHLAKMGAHVVVTARSKETLQKVV
SHCLELGAASAHYIAGTMEDMTFAEQFVAQAGKLMGGLDMLILNHITNTS
LNLFHDDIHHVRKSMEVNFLSYVVLTVAALPMLKQSNGSIVVVSSLAGKV
AYPMVAAYSASKFALDGFFSSIRKEYSVSRVNVSITLCVLGLIDTETAMK
AVSGIVHMQAAPKEECALEIIKGGALRQEEVYYDSSLWTTLLIRNPSRKI
LEFLYST
Ligand information
Ligand IDNN4
InChIInChI=1S/C22H30N2O4/c1-21(2,28-17-6-4-16(27-3)5-7-17)20(26)24-18-14-8-13-9-15(18)12-22(10-13,11-14)19(23)25/h4-7,13-15,18H,8-12H2,1-3H3,(H2,23,25)(H,24,26)/t13-,14-,15+,18-,22-
InChIKeyMNVKIDPRYUGTTG-YINOZDTMSA-N
SMILES
SoftwareSMILES
OpenEye OEToolkits 1.5.0CC(C)(C(=O)NC1C2CC3CC1CC(C3)(C2)C(=O)N)Oc4ccc(cc4)OC
CACTVS 3.341COc1ccc(OC(C)(C)C(=O)NC2[CH]3CC4C[CH]2CC(C4)(C3)C(N)=O)cc1
ACDLabs 10.04O=C(N)C14CC3CC(CC(C1)C3NC(=O)C(Oc2ccc(OC)cc2)(C)C)C4
OpenEye OEToolkits 1.5.0CC(C)(C(=O)NC1[C@H]2CC3C[C@@H]1CC(C3)(C2)C(=O)N)Oc4ccc(cc4)OC
CACTVS 3.341COc1ccc(OC(C)(C)C(=O)NC2[C@H]3CC4C[C@@H]2CC(C4)(C3)C(N)=O)cc1
FormulaC22 H30 N2 O4
Name(1S,3R,4S,5S,7S)-4-{[2-(4-METHOXYPHENOXY)-2-METHYLPROPANOYL]AMINO}ADAMANTANE-1-CARBOXAMIDE
ChEMBL
DrugBankDB08280
ZINCZINC000100036578
PDB chain2irw Chain C Residue 911 [Download ligand structure] [Download structure with residue number starting from 1] [View ligand structure]
Receptor-Ligand Complex Structure
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PDB2irw Discovery of adamantane ethers as inhibitors of 11beta-HSD-1: Synthesis and biological evaluation.
Resolution3.1 Å
Binding residue
(original residue number in PDB)		I121 S170 Y177 Y183 T222 A223 V231 M233
Binding residue
(residue number reindexed from 1)		I96 S145 Y152 Y158 T197 A198 V206 M208
Annotation score1
Enzymatic activity
Catalytic site (original residue number in PDB) S170 Y183 K187
Catalytic site (residue number reindexed from 1) S145 Y158 K162
Enzyme Commision number 1.1.1.146: 11beta-hydroxysteroid dehydrogenase.
1.1.1.201: 7beta-hydroxysteroid dehydrogenase (NADP(+)).
Gene Ontology
Molecular Function
GO:0005496 steroid binding
GO:0016491 oxidoreductase activity
GO:0042803 protein homodimerization activity
GO:0047022 7-beta-hydroxysteroid dehydrogenase (NADP+) activity
GO:0050661 NADP binding
GO:0070524 11-beta-hydroxysteroid dehydrogenase (NADP+) activity
GO:0102196 cortisol dehydrogenase activity
Biological Process
GO:0006706 steroid catabolic process
GO:0008202 steroid metabolic process
GO:0030324 lung development
Cellular Component
GO:0005783 endoplasmic reticulum
GO:0005789 endoplasmic reticulum membrane
GO:0016020 membrane
GO:0043231 intracellular membrane-bounded organelle

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Molecular Function
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Biological Process
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Cellular Component
External links
PDB RCSB:2irw, PDBe:2irw, PDBj:2irw
PDBsum2irw
PubMed17110106
UniProtP28845|DHI1_HUMAN 11-beta-hydroxysteroid dehydrogenase 1 (Gene Name=HSD11B1)

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