Structure of PDB 3eyl Chain A Binding Site BS02

Receptor Information

>3eyl Chain A (length=101) Species: 9606 (Homo sapiens)

TNLPRNPSMADYEARIFTFGTWIYSVNKEQLARAGFYALGEGDKVKCFHC
GGGLTDWKPSEDPWEQHAKWYPGCKYLLEQKGQEYINNIHLTHSLEECLV
R

Ligand information

• Ligand ID: SMK
• InChI: InChI=1S/C29H39N5O3/c1-2-23(31)27(35)33-26-21(17-18-30)13-14-22-15-16-24(34(22)29(26)37)28(36)32-25(19-9-5-3-6-10-19)20-11-7-4-8-12-20/h3-12,21-26H,2,13-18,30-31H2,1H3,(H,32,36)(H,33,35)/t21-,22+,23+,24+,26+/m1/s1
• InChIKey: KQHWCFZCUNTTCW-VEGWMBEDSA-N
• SMILES:
  OpenEye OEToolkits 1.5.0: CCC(C(=O)NC1C(CCC2CCC(N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4)CCN)N
  OpenEye OEToolkits 1.5.0: CC[C@@H](C(=O)N[C@H]1[C@H](CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4)CCN)N
  CACTVS 3.341: CC[C@H](N)C(=O)N[C@H]1[C@@H](CCN)CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4
  CACTVS 3.341: CC[CH](N)C(=O)N[CH]1[CH](CCN)CC[CH]2CC[CH](N2C1=O)C(=O)NC(c3ccccc3)c4ccccc4
  ACDLabs 10.04: O=C(NC(c1ccccc1)c2ccccc2)C4N3C(=O)C(NC(=O)C(N)CC)C(CCC3CC4)CCN
• Formula: C29 H39 N5 O3
• Name: (3S,6S,7R,9aS)-6-{[(2S)-2-aminobutanoyl]amino}-7-(2-aminoethyl)-N-(diphenylmethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamide
• ChEMBL: CHEMBL574027
• ZINC: ZINC000039205347
• PDB chain: 3eyl Chain A Residue 600

Receptor-Ligand Complex Structure

Structure summary

• PDB: 3eyl Designing Smac-mimetics as antagonists of XIAP, cIAP1, and cIAP2.
• Resolution: 3.0 Å
• Binding residue (original residue number in PDB): K297 G306 L307 T308 D309 W310 E314 Q319 W323
• Binding residue (residue number reindexed from 1): K44 G53 L54 T55 D56 W57 E61 Q66 W70
• Annotation score: 1
• Binding affinity: PDBbind-CN: -logKd/Ki=6.60,IC50=250nM
  BindingDB: IC50=86nM

Enzymatic activity

• Enzyme Commision number: 2.3.2.27: RING-type E3 ubiquitin transferase.

External links

• PDB: RCSB:3eyl, PDBe:3eyl, PDBj:3eyl
• PDBsum: 3eyl
• PubMed: 18992220
• UniProt: P98170|XIAP_HUMAN E3 ubiquitin-protein ligase XIAP (Gene Name=XIAP)