{"reference": "J Am Chem Soc. 2011 May 4;133(17):6736-44.", "alternative_name": "", "entry": "S-0296", "gene_names": "", "remarks": "AIIFL segment derived from Alzheimer's Amyloid-Beta displayed on 42-membered macrocycle scaffold", "secondary_structure": "AIIFLAXYKA#CCCBCCCCCC&AIIFLAXYKA#CCCBCCCCCC&AIIFLAXYKA#CCCBCCCCCC&AIIFLAXYKA#CCCBCCCCCC&AIIFLAXYKA#CCCBCCCCCC&AIIFLAXYKA#CCCBCCCCCC&AIIFLAXYKA#CCCBCCCCCC&AIIFLAXYKA#CCCBCCCCCC", "chain_id": "A%%A%%A%%B%%B%%B%%B%%C%%C%%C%%D%%D%%D%%E%%E%%E%%E%%F%%F%%F%%F%%G%%G%%G%%H%%H%%H", "inchi": "InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1%%InChI=1S/Zn/q+2%%InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2%%InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1%%InChI=1S/Zn/q+2%%InChI=1S/ClH/h1H/p-1%%InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1%%InChI=1S/ClH/h1H/p-1%%InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1%%InChI=1S/ClH/h1H/p-1%%InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1%%InChI=1S/Zn/q+2%%InChI=1S/ClH/h1H/p-1%%InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1%%InChI=1S/Zn/q+2%%InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2%%InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1%%InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2%%InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17)%%InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1", "amyloid_non_amyloid": "Amyloid", "pmid": "21473620", "ligand_smiles": "COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN%%[Zn+2]%%C(C(CO)O)O%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN%%[Zn+2]%%[Cl-]%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN%%[Cl-]%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN%%[Cl-]%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN%%[Zn+2]%%[Cl-]%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN%%[Zn+2]%%C(C(CO)O)O%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN%%C(C(CO)O)O%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C(C[C@@H](C(=O)O)N)CN", "keyword": "Cyclic pseudo-peptide AIIFL(ORN)(HAO)YK(ORN)", "peptide_protein_sequence": "chain-ID A: AIIFLAXYKA; chain-ID B: AIIFLAXYKA; chain-ID C: AIIFLAXYKA; chain-ID D: AIIFLAXYKA; chain-ID E: AIIFLAXYKA; chain-ID F: AIIFLAXYKA; chain-ID G: AIIFLAXYKA; chain-ID H: AIIFLAXYKA", "uniprot_ac": "", "protein_name": "Amyloid-Beta", "r_value_free": "0.223", "mutation_s_field": "No", "ligand_mw": "253.21%%132.16%%65.41%%92.09%%253.21%%132.16%%65.41%%35.45%%253.21%%132.16%%35.45%%253.21%%132.16%%35.45%%253.21%%132.16%%65.41%%35.45%%253.21%%132.16%%65.41%%92.09%%253.21%%132.16%%92.09%%253.21%%132.16", "pdb_id": "3Q9J", "inchi_key": "GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%PTFCDOFLOPIGGS-UHFFFAOYSA-N%%PEDCQBHIVMGVHV-UHFFFAOYSA-N%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%PTFCDOFLOPIGGS-UHFFFAOYSA-N%%VEXZGXHMUGYJMC-UHFFFAOYSA-M%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%VEXZGXHMUGYJMC-UHFFFAOYSA-M%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%VEXZGXHMUGYJMC-UHFFFAOYSA-M%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%PTFCDOFLOPIGGS-UHFFFAOYSA-N%%VEXZGXHMUGYJMC-UHFFFAOYSA-M%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%PTFCDOFLOPIGGS-UHFFFAOYSA-N%%PEDCQBHIVMGVHV-UHFFFAOYSA-N%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%PEDCQBHIVMGVHV-UHFFFAOYSA-N%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N", "ec_number": "", "pdb_classification": "PROTEIN FIBRIL", "type": "Fibril", "author": "Liu, C., Sawaya, M.R., Cheng, P.N., Zheng, J., Nowick, J.S., Eisenberg, D.", "species": "", "ligand_id": "HAO%%ORN%%ZN%%GOL%%HAO%%ORN%%ZN%%CL%%HAO%%ORN%%CL%%HAO%%ORN%%CL%%HAO%%ORN%%ZN%%CL%%HAO%%ORN%%ZN%%GOL%%HAO%%ORN%%GOL%%HAO%%ORN", "method": "X-RAY DIFFRACTION", "ligand_name": "{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine%%ZINC ION%%GLYCEROL%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine%%ZINC ION%%CHLORIDE ION%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine%%CHLORIDE ION%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine%%CHLORIDE ION%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine%%ZINC ION%%CHLORIDE ION%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine%%ZINC ION%%GLYCEROL%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine%%GLYCEROL%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%L-ornithine", "global_stoichiometry": "Homo 4-mer - A4 ", "resolution": "2.55", "ligand_formula": "C10 H11 N3 O5%%C5 H12 N2 O2%%Zn 2%%C3 H8 O3%%C10 H11 N3 O5%%C5 H12 N2 O2%%Zn 2%%Cl -1%%C10 H11 N3 O5%%C5 H12 N2 O2%%Cl -1%%C10 H11 N3 O5%%C5 H12 N2 O2%%Cl -1%%C10 H11 N3 O5%%C5 H12 N2 O2%%Zn 2%%Cl -1%%C10 H11 N3 O5%%C5 H12 N2 O2%%Zn 2%%C3 H8 O3%%C10 H11 N3 O5%%C5 H12 N2 O2%%C3 H8 O3%%C10 H11 N3 O5%%C5 H12 N2 O2", "length": "10", "ligstr": "HAO:A:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:A:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N;ZN:A:Zn 2:65.41:ZINC ION:[Zn+2]:InChI=1S/Zn/q+2:PTFCDOFLOPIGGS-UHFFFAOYSA-N;GOL:B:C3 H8 O3:92.09:GLYCEROL:C(C(CO)O)O:InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2:PEDCQBHIVMGVHV-UHFFFAOYSA-N;HAO:B:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:B:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N;ZN:B:Zn 2:65.41:ZINC ION:[Zn+2]:InChI=1S/Zn/q+2:PTFCDOFLOPIGGS-UHFFFAOYSA-N;CL:C:Cl -1:35.45:CHLORIDE ION:[Cl-]:InChI=1S/ClH/h1H/p-1:VEXZGXHMUGYJMC-UHFFFAOYSA-M;HAO:C:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:C:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N;CL:D:Cl -1:35.45:CHLORIDE ION:[Cl-]:InChI=1S/ClH/h1H/p-1:VEXZGXHMUGYJMC-UHFFFAOYSA-M;HAO:D:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:D:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N;CL:E:Cl -1:35.45:CHLORIDE ION:[Cl-]:InChI=1S/ClH/h1H/p-1:VEXZGXHMUGYJMC-UHFFFAOYSA-M;HAO:E:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:E:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N;ZN:E:Zn 2:65.41:ZINC ION:[Zn+2]:InChI=1S/Zn/q+2:PTFCDOFLOPIGGS-UHFFFAOYSA-N;CL:F:Cl -1:35.45:CHLORIDE ION:[Cl-]:InChI=1S/ClH/h1H/p-1:VEXZGXHMUGYJMC-UHFFFAOYSA-M;HAO:F:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:F:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N;ZN:F:Zn 2:65.41:ZINC ION:[Zn+2]:InChI=1S/Zn/q+2:PTFCDOFLOPIGGS-UHFFFAOYSA-N;GOL:G:C3 H8 O3:92.09:GLYCEROL:C(C(CO)O)O:InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2:PEDCQBHIVMGVHV-UHFFFAOYSA-N;HAO:G:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:G:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N;GOL:H:C3 H8 O3:92.09:GLYCEROL:C(C(CO)O)O:InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2:PEDCQBHIVMGVHV-UHFFFAOYSA-N;HAO:H:C10 H11 N3 O5:253.21:{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid:COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O:InChI=1S/C10H11N3O5/c1-18-7-3-2-5(12-9(15)10(16)17)4-6(7)8(14)13-11/h2-4H,11H2,1H3,(H,12,15)(H,13,14)(H,16,17):GRLLMVZTTMERGI-UHFFFAOYSA-N;ORN:H:C5 H12 N2 O2:132.16:L-ornithine:C(C[C@@H](C(=O)O)N)CN:InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1:AHLPHDHHMVZTML-BYPYZUCNSA-N", "description": "They explore oligomer structure using a model system: macrocyclic peptides. Key amyloidogenic sequences from ABeta and tau were incorporated into macrocycles, thereby restraining them to Beta-strands, but limiting the growth of the oligomers so they may crystallize and cannot fibrillate. Oligomers reveal tetrameric interfaces in which Beta-sheet dimers pair together by highly complementary, dry interfaces, analogous to steric zippers found in fibers, suggesting a common structure for amyloid oligomers and fibers. In amyloid fibers, the axes of the paired sheets are either parallel or antiparallel, whereas the oligomeric interfaces display a variety of sheet-to-sheet pairing angles, offering a structural explanation for the heterogeneity of amyloid oligomers."}