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TitleDesign and Synthesis of Potent Inhibitor of Apoptosis (IAP) Proteins Antagonists Bearing an Octahydropyrrolo[1,2-a]pyrazine Scaffold as a Novel Proline Mimetic.
Journal, issue, pagesJ. Med. Chem., Vol. 56, Page 1228-1246, Year 2013
Publish dateNov 12, 2012 (structure data deposition date)
AuthorsHashimoto, K. / Saito, B. / Miyamoto, N. / Oguro, Y. / Tomita, D. / Shiokawa, Z. / Asano, M. / Kakei, H. / Taya, N. / Kawasaki, M. ...Hashimoto, K. / Saito, B. / Miyamoto, N. / Oguro, Y. / Tomita, D. / Shiokawa, Z. / Asano, M. / Kakei, H. / Taya, N. / Kawasaki, M. / Sumi, H. / Yabuki, M. / Iwai, K. / Yoshida, S. / Yoshimatsu, M. / Aoyama, K. / Kosugi, Y. / Kojima, T. / Morishita, N. / Dougan, D.R. / Snell, G.P. / Imamura, S. / Ishikawa, T.
External linksJ. Med. Chem. / PubMed:23298277
MethodsX-ray diffraction
Resolution1.249 - 2.84 Å
Structure data

PDB-4hy0:
Crystal structure of XIAP BIR3 with T3256336
Method: X-RAY DIFFRACTION / Resolution: 2.84 Å

PDB-4hy4:
Crystal structure of cIAP1 BIR3 bound to T3170284
Method: X-RAY DIFFRACTION / Resolution: 1.249 Å

PDB-4hy5:
Crystal structure of cIAP1 BIR3 bound to T3256336
Method: X-RAY DIFFRACTION / Resolution: 1.752 Å

Chemicals

ChemComp-ZN:
Unknown entry

ChemComp-1AQ:
(3S,7R,8aR)-2-{(2S)-2-(4,4-difluorocyclohexyl)-2-[(N-methyl-L-alanyl)amino]acetyl}-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-ethoxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

ChemComp-HOH:
WATER

ChemComp-1BG:
(3S,8aR)-2-{(2S)-2-cyclohexyl-2-[(N-methyl-L-alanyl)amino]acetyl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide

Source
  • homo sapiens (human)
KeywordsLIGASE/LIGASE INHIBITOR / BIR3 / Baculoviral IAP repeat-containing protein 4 / Apoptotic suppressor. Inhibitor of caspase-3 / -7 and -9. / Interacts with SMAC and with PRSS25 / XIAP / BIRC4 / X-linked inhibitor of apoptosis / LIGASE-LIGASE INHIBITOR complex / IAP family / BIR repeats / CARD domain / RING-type zinc finger

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