Structure of PDB 5irq Chain A Binding Site BS02

Receptor Information
>5irq Chain A (length=466) Species: 9606 (Homo sapiens) [Search protein sequence] [Download receptor structure] [Download structure with residue number starting from 1] [View receptor structure]
LLSLPLVGSLPFLPRHGHMHNNFFKLQKKYGPIYSVRMGTKTTVIVGHHQ
LAKEVLIKKGKDFSGRPQMATLDIASNNRKGIAFADSGAHWQLHRRLAMA
TFALFKDGDQKLEKIICQEISTLCDMLATHNGQSIDISFPVFVAVTNVIS
LICFNTSYKNGDPELNVIQNYNEGIIDNLSKDSLVDLVPWLKIFPNKTLE
KLKSHVKIRNDLLNKILENYKEKFRSDSITNMLDTLMQAKMNSDNDSELL
SDNHILTTIGDIFGAGVETTTSVVKWTLAFLLHNPQVKKKLYEEIDQNVG
FSRTPTISDRNRLLLLEATIREVLRLRPVAPMLIPHKANVDSSIGEFAVD
KGTEVIINLWALHHNEKEWHQPDQFMPERFLNPAGTQLISPSVSYLPFGA
GPRSCIGEILARQELFLIMAWLLQRFDLEVPDDGQLPSLEGIPKVVFLID
SFKVKIKVRQAWREAQ
Ligand information
Ligand ID6D7
InChIInChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)/t18-/m1/s1
InChIKeyOZPFIJIOIVJZMN-GOSISDBHSA-N
SMILES
SoftwareSMILES
OpenEye OEToolkits 2.0.4CNC(=O)c1ccc2cc(ccc2c1)[C@@]3(CCn4c3cnc4)O
CACTVS 3.385CNC(=O)c1ccc2cc(ccc2c1)[C]3(O)CCn4cncc34
CACTVS 3.385CNC(=O)c1ccc2cc(ccc2c1)[C@]3(O)CCn4cncc34
OpenEye OEToolkits 2.0.4CNC(=O)c1ccc2cc(ccc2c1)C3(CCn4c3cnc4)O
ACDLabs 12.01C3(c1cc2c(cc1)cc(C(NC)=O)cc2)(CCn4cncc34)O
FormulaC18 H17 N3 O2
Name(R)-orteronel;
6-[(7R)-7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methylnaphthalene-2-carboxamide
ChEMBLCHEMBL1921985
DrugBank
ZINCZINC000000003322
PDB chain5irq Chain A Residue 601 [Download ligand structure] [Download structure with residue number starting from 1] [View ligand structure]
Receptor-Ligand Complex Structure
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PDB5irq Structural and Functional Evaluation of Clinically Relevant Inhibitors of Steroidogenic Cytochrome P450 17A1.
Resolution2.202 Å
Binding residue
(original residue number in PDB)		Y201 N202 G301 A302
Binding residue
(residue number reindexed from 1)		Y171 N172 G264 A265
Annotation score1
Binding affinityBindingDB: IC50=38nM
Enzymatic activity
Catalytic site (original residue number in PDB) T306 F435 C442
Catalytic site (residue number reindexed from 1) T269 F398 C405
Enzyme Commision number 1.14.14.19: steroid 17alpha-monooxygenase.
1.14.14.32: 17alpha-hydroxyprogesterone deacetylase.
Gene Ontology
Molecular Function
GO:0004497 monooxygenase activity
GO:0004508 steroid 17-alpha-monooxygenase activity
GO:0005506 iron ion binding
GO:0008395 steroid hydroxylase activity
GO:0016705 oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
GO:0016829 lyase activity
GO:0019825 oxygen binding
GO:0020037 heme binding
GO:0046872 metal ion binding
Biological Process
GO:0006694 steroid biosynthetic process
GO:0006702 androgen biosynthetic process
GO:0006704 glucocorticoid biosynthetic process
GO:0007548 sex differentiation
GO:0008202 steroid metabolic process
GO:0042445 hormone metabolic process
GO:0042446 hormone biosynthetic process
GO:0042448 progesterone metabolic process
Cellular Component
GO:0005783 endoplasmic reticulum
GO:0005789 endoplasmic reticulum membrane
GO:0016020 membrane
GO:0030424 axon
GO:0043025 neuronal cell body

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Molecular Function
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Biological Process
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Cellular Component
External links
PDB RCSB:5irq, PDBe:5irq, PDBj:5irq
PDBsum5irq
PubMed28373265
UniProtP05093|CP17A_HUMAN Steroid 17-alpha-hydroxylase/17,20 lyase (Gene Name=CYP17A1)

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