Structure of PDB 4hfr Chain B Binding Site BS02

Receptor Information
>4hfr Chain B (length=253) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
EFRPEMLQGKKVIVTGASKGIGREMAYHLAKMGAHVVVTARSKETLQKVV
SHCLELGAASAHYIAGTMEDMTFAEQFVAQAGKLMGGLDMLILNHITNTS
LNLFHDDIHHVRKSMEVNFLSYVVLTVAALPMLKQSNGSIVVVSSLAGKV
AYPLVAAYSASKFALDGFFSSIRKEYSVSRVNVSITLCVLGLIDTETAMK
AVMQAAPKEECALEIIKGGALRQEEVYYDSSRWTTLLIRNPSRKILEELY
STS
Ligand information
Ligand ID14M
InChIInChI=1S/C22H33N3O3S/c1-2-13-29-22-18(21(28)23-17-8-4-3-5-9-17)10-11-19(24-22)25-12-6-7-16(15-25)14-20(26)27/h10-11,16-17H,2-9,12-15H2,1H3,(H,23,28)(H,26,27)/t16-/m0/s1
InChIKeyNCDZABJPWMBMIQ-INIZCTEOSA-N
SMILES
SoftwareSMILES
OpenEye OEToolkits 1.7.6CCCSc1c(ccc(n1)N2CCCC(C2)CC(=O)O)C(=O)NC3CCCCC3
OpenEye OEToolkits 1.7.6CCCSc1c(ccc(n1)N2CCC[C@H](C2)CC(=O)O)C(=O)NC3CCCCC3
ACDLabs 12.01O=C(O)CC3CCCN(c2nc(SCCC)c(C(=O)NC1CCCCC1)cc2)C3
CACTVS 3.370CCCSc1nc(ccc1C(=O)NC2CCCCC2)N3CCC[CH](C3)CC(O)=O
CACTVS 3.370CCCSc1nc(ccc1C(=O)NC2CCCCC2)N3CCC[C@H](C3)CC(O)=O
FormulaC22 H33 N3 O3 S
Name{(3S)-1-[5-(cyclohexylcarbamoyl)-6-(propylsulfanyl)pyridin-2-yl]piperidin-3-yl}acetic acid
ChEMBLCHEMBL2153191
DrugBankDB14875
ZINCZINC000095575356
PDB chain4hfr Chain B Residue 302 [Download ligand structure] [Download structure with residue number starting from 1] [View ligand structure]
Receptor-Ligand Complex Structure
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PDB4hfr Discovery of a Potent, Selective, and Orally Bioavailable Acidic 11 -Hydroxysteroid Dehydrogenase Type 1 (11 -HSD1) Inhibitor: Discovery of 2-[(3S)-1-[5-(Cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-piperidyl]acetic Acid (AZD4017)
Resolution2.73 Å
Binding residue
(original residue number in PDB)		S170 Y177 V180 Y183 G216 L217 D259
Binding residue
(residue number reindexed from 1)		S145 Y152 V155 Y158 G191 L192 D229
Annotation score1
Binding affinityBindingDB: IC50=7nM
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:4hfr, PDBe:4hfr, PDBj:4hfr
PDBsum4hfr
PubMed22691057
UniProtP28845|DHI1_HUMAN 11-beta-hydroxysteroid dehydrogenase 1 (Gene Name=HSD11B1)

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