{"method": "X-RAY DIFFRACTION", "mutation_s_field": "No", "ec_number": "", "description": "They designed out-of-register Beta-sheet amyloid mimics, which form both cylindrin-like oligomers and fibrils, and these mimics are cytotoxic. Structural and energetic considerations suggest that out-of-register fibrils can readily convert to toxic cylindrins. We propose that out-of-register Beta-sheets and their related cylindrins are part of a toxic amyloid pathway, which is distinct from the more energetically favored in-register amyloid pathway.", "ligstr": "4BF:A:C9 H10 Br N O2:244.09:4-BROMO-L-PHENYLALANINE:c1cc(ccc1C[C@@H](C(=O)O)N)Br:InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1:PEMUHKUIQHFMTH-QMMMGPOBSA-N;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;MPD:A:C6 H14 O2:118.17:(4S)-2-METHYL-2,4-PENTANEDIOL:C[C@@H](CC(C)(C)O)O:InChI=1S/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1:SVTBMSDMJJWYQN-YFKPBYRVSA-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;4BF:B:C9 H10 Br N O2:244.09:4-BROMO-L-PHENYLALANINE:c1cc(ccc1C[C@@H](C(=O)O)N)Br:InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1:PEMUHKUIQHFMTH-QMMMGPOBSA-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;MPD:B:C6 H14 O2:118.17:(4S)-2-METHYL-2,4-PENTANEDIOL:C[C@@H](CC(C)(C)O)O:InChI=1S/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1:SVTBMSDMJJWYQN-YFKPBYRVSA-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;PO4:B:O4 P -3:94.97:PHOSPHATE ION:[O-]P(=O)([O-])[O-]:InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3:NBIIXXVUZAFLBC-UHFFFAOYSA-K;4BF:C:C9 H10 Br N O2:244.09:4-BROMO-L-PHENYLALANINE:c1cc(ccc1C[C@@H](C(=O)O)N)Br:InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1:PEMUHKUIQHFMTH-QMMMGPOBSA-N;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;MPD:C:C6 H14 O2:118.17:(4S)-2-METHYL-2,4-PENTANEDIOL:C[C@@H](CC(C)(C)O)O:InChI=1S/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1:SVTBMSDMJJWYQN-YFKPBYRVSA-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;4BF:D:C9 H10 Br N O2:244.09:4-BROMO-L-PHENYLALANINE:c1cc(ccc1C[C@@H](C(=O)O)N)Br:InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1:PEMUHKUIQHFMTH-QMMMGPOBSA-N;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;MPD:D:C6 H14 O2:118.17:(4S)-2-METHYL-2,4-PENTANEDIOL:C[C@@H](CC(C)(C)O)O:InChI=1S/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1:SVTBMSDMJJWYQN-YFKPBYRVSA-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;PO4:D:O4 P -3:94.97:PHOSPHATE ION:[O-]P(=O)([O-])[O-]:InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3:NBIIXXVUZAFLBC-UHFFFAOYSA-K", "pmid": "23213214", "remarks": "SVQIVYK segment from human Tau (305-311) displayed on 54-membered macrocycle scaffold (form III)", "amyloid_non_amyloid": "Amyloid", "type": "Fibril", "inchi": "InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1%%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/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1%%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/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1%%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/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1%%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/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3%%InChI=1S/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1%%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/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1%%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/C9H10BrNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1%%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/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3/t5-/m0/s1%%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/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3", "resolution": "1.82", "species": "Homo sapiens", "secondary_structure": "ASVQIVYKAEFXYK#CCCCEEECCCCCCC&ASVQIVYKAEFXYK#CCCCEEECCCCCCC&ASVQIVYKAEFXYK#CCCCEEECCCCCCC&ASVQIVYKAEFXYK#CCCCEEECCCCCCC", "chain_id": "A%%A%%A%%A%%B%%B%%B%%B%%B%%C%%C%%C%%C%%D%%D%%D%%D%%D", "gene_names": "", "r_value_free": "0.22899999", "pdb_id": "4E0O", "reference": "Proc Natl Acad Sci U S A. 2012 Dec 18;109(51):20913-8.", "keyword": "Cyclic pseudo-peptide SVQIVYK(ORN)EF(HAO)(4BF)K(ORN)", "protein_name": "Microtubule-associated protein tau", "ligand_formula": "C9 H10 Br N O2%%C10 H11 N3 O5%%C6 H14 O2%%C5 H12 N2 O2%%C9 H10 Br N O2%%C10 H11 N3 O5%%C6 H14 O2%%C5 H12 N2 O2%%O4 P -3%%C9 H10 Br N O2%%C10 H11 N3 O5%%C6 H14 O2%%C5 H12 N2 O2%%C9 H10 Br N O2%%C10 H11 N3 O5%%C6 H14 O2%%C5 H12 N2 O2%%O4 P -3", "peptide_protein_sequence": "chain-ID A: ASVQIVYKAEFXYK; chain-ID B: ASVQIVYKAEFXYK; chain-ID C: ASVQIVYKAEFXYK; chain-ID D: ASVQIVYKAEFXYK", "entry": "S-0316", "length": "14", "uniprot_ac": "P10636", "author": "Liu, C., Zhao, M., Jiang, L., Cheng, P.N., Park, J., Sawaya, M.R., Pensalfini, A., Gou, D., Berk, A.J., Glabe, C.G., Nowick, J., Eisenberg, D.", "ligand_smiles": "c1cc(ccc1C[C@@H](C(=O)O)N)Br%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C[C@@H](CC(C)(C)O)O%%C(C[C@@H](C(=O)O)N)CN%%c1cc(ccc1C[C@@H](C(=O)O)N)Br%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C[C@@H](CC(C)(C)O)O%%C(C[C@@H](C(=O)O)N)CN%%[O-]P(=O)([O-])[O-]%%c1cc(ccc1C[C@@H](C(=O)O)N)Br%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C[C@@H](CC(C)(C)O)O%%C(C[C@@H](C(=O)O)N)CN%%c1cc(ccc1C[C@@H](C(=O)O)N)Br%%COc1ccc(cc1C(=O)NN)NC(=O)C(=O)O%%C[C@@H](CC(C)(C)O)O%%C(C[C@@H](C(=O)O)N)CN%%[O-]P(=O)([O-])[O-]", "ligand_mw": "244.09%%253.21%%118.17%%132.16%%244.09%%253.21%%118.17%%132.16%%94.97%%244.09%%253.21%%118.17%%132.16%%244.09%%253.21%%118.17%%132.16%%94.97", "alternative_name": "", "ligand_name": "4-BROMO-L-PHENYLALANINE%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%(4S)-2-METHYL-2,4-PENTANEDIOL%%L-ornithine%%4-BROMO-L-PHENYLALANINE%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%(4S)-2-METHYL-2,4-PENTANEDIOL%%L-ornithine%%PHOSPHATE ION%%4-BROMO-L-PHENYLALANINE%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%(4S)-2-METHYL-2,4-PENTANEDIOL%%L-ornithine%%4-BROMO-L-PHENYLALANINE%%{[3-(hydrazinocarbonyl)-4-methoxyphenyl]amino}(oxo)acetic acid%%(4S)-2-METHYL-2,4-PENTANEDIOL%%L-ornithine%%PHOSPHATE ION", "pdb_classification": "PROTEIN FIBRIL", "global_stoichiometry": "Homo 2-mer - A2 ", "inchi_key": "PEMUHKUIQHFMTH-QMMMGPOBSA-N%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%SVTBMSDMJJWYQN-YFKPBYRVSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%PEMUHKUIQHFMTH-QMMMGPOBSA-N%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%SVTBMSDMJJWYQN-YFKPBYRVSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%NBIIXXVUZAFLBC-UHFFFAOYSA-K%%PEMUHKUIQHFMTH-QMMMGPOBSA-N%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%SVTBMSDMJJWYQN-YFKPBYRVSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%PEMUHKUIQHFMTH-QMMMGPOBSA-N%%GRLLMVZTTMERGI-UHFFFAOYSA-N%%SVTBMSDMJJWYQN-YFKPBYRVSA-N%%AHLPHDHHMVZTML-BYPYZUCNSA-N%%NBIIXXVUZAFLBC-UHFFFAOYSA-K", "ligand_id": "4BF%%HAO%%MPD%%ORN%%4BF%%HAO%%MPD%%ORN%%PO4%%4BF%%HAO%%MPD%%ORN%%4BF%%HAO%%MPD%%ORN%%PO4"}