data_OSC # _chem_comp.id OSC _chem_comp.name "(2R,3AS,6R,7AS)-N-(2-{1-[AMINO(IMINO)METHYL]-2,5-DIHYDRO-1H-PYRROL-3-YL}ETHYL)-6-HYDROXY-1-{N-[(2S)-2-HYDROXY-3-PHENYLPROPANOYL]PHENYLALANYL}OCTAHYDRO-1H-INDOLE-2-CARBOXAMIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C34 H44 N6 O5" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "OSCILLARIN; (2R,3AS,6R,7AS)-6-HYDROXY-1-{(2R)-2-[(2R)-2-HYDROXY-3-PHENYL-PROPIONYLAMINO]-3-PHENYL-PROPIONYL}-OCTAHYDORO-INDOLE-2-CARBOXYLIC ACID [2-(1-CARBAMIMIDOYL-2,5-DIHYDRO-1H-PYRROL-3-YL)-ETHYL]-AMIDE" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2004-01-14 _chem_comp.pdbx_modified_date 2020-05-27 _chem_comp.pdbx_ambiguous_flag N _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 616.750 _chem_comp.one_letter_code ? _chem_comp.three_letter_code OSC _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details ? _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 1RIW _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # loop_ _chem_comp_atom.comp_id _chem_comp_atom.atom_id _chem_comp_atom.alt_atom_id _chem_comp_atom.type_symbol _chem_comp_atom.charge _chem_comp_atom.pdbx_align _chem_comp_atom.pdbx_aromatic_flag _chem_comp_atom.pdbx_leaving_atom_flag _chem_comp_atom.pdbx_stereo_config _chem_comp_atom.model_Cartn_x _chem_comp_atom.model_Cartn_y _chem_comp_atom.model_Cartn_z _chem_comp_atom.pdbx_model_Cartn_x_ideal _chem_comp_atom.pdbx_model_Cartn_y_ideal _chem_comp_atom.pdbx_model_Cartn_z_ideal _chem_comp_atom.pdbx_component_atom_id _chem_comp_atom.pdbx_component_comp_id _chem_comp_atom.pdbx_ordinal OSC N1 N1 N 0 1 N N N 18.405 -13.548 21.865 0.029 -2.128 1.090 N1 OSC 1 OSC C2 C2 C 0 1 N N S 19.490 -14.384 21.258 -0.312 -3.447 0.540 C2 OSC 2 OSC C3 C3 C 0 1 N N S 18.381 -12.247 21.149 1.358 -2.233 1.718 C3 OSC 3 OSC C4 C4 C 0 1 N N N 17.584 -13.915 22.906 -0.732 -1.018 1.017 C4 OSC 4 OSC C5 C5 C 0 1 N N S 20.493 -13.319 20.759 1.033 -4.144 0.263 C5 OSC 5 OSC C6 C6 C 0 1 N N N 18.924 -15.308 20.127 -1.186 -3.351 -0.696 C6 OSC 6 OSC C7 C7 C 0 1 N N N 19.520 -12.306 20.109 1.855 -3.680 1.505 C7 OSC 7 OSC C8 C8 C 0 1 N N N 17.069 -12.027 20.446 2.311 -1.263 1.067 C8 OSC 8 OSC C9 C9 C 0 1 N N R 17.736 -15.277 23.556 -2.133 -1.100 0.468 C9 OSC 9 OSC O10 O10 O 0 1 N N N 16.726 -13.146 23.322 -0.290 0.046 1.395 O10 OSC 10 OSC C11 C11 C 0 1 N N N 21.471 -13.836 19.681 1.723 -3.547 -0.965 C11 OSC 11 OSC C12 C12 C 0 1 N N R 20.035 -15.917 19.243 -0.440 -2.725 -1.874 C12 OSC 12 OSC N13 N13 N 0 1 N N N 16.595 -10.768 20.288 3.549 -1.093 1.571 N13 OSC 13 OSC O14 O14 O 0 1 N N N 16.452 -12.984 20.021 1.963 -0.635 0.089 O14 OSC 14 OSC C15 C15 C 0 1 N N N 18.188 -15.147 25.026 -2.930 -2.141 1.256 C15 OSC 15 OSC N16 N16 N 0 1 N N N 16.458 -15.976 23.466 -2.783 0.208 0.590 N16 OSC 16 OSC C17 C17 C 0 1 N N N 20.840 -14.758 18.594 0.794 -3.583 -2.176 C17 OSC 17 OSC O18 O18 O 0 1 N N N 20.903 -16.743 20.027 -1.292 -2.687 -3.020 O18 OSC 18 OSC C19 C19 C 0 1 N N N 15.324 -10.527 19.595 4.474 -0.150 0.938 C19 OSC 19 OSC C20 C20 C 0 1 Y N N 19.635 -14.680 25.088 -4.299 -2.294 0.644 C20 OSC 20 OSC C21 C21 C 0 1 N N N 16.359 -17.146 22.783 -3.791 0.540 -0.241 C21 OSC 21 OSC C22 C22 C 0 1 N N N 14.423 -9.610 20.441 5.801 -0.148 1.701 C22 OSC 22 OSC C23 C23 C 0 1 Y N N 19.947 -13.418 25.640 -4.509 -3.227 -0.354 C23 OSC 23 OSC C24 C24 C 0 1 Y N N 20.678 -15.505 24.588 -5.346 -1.506 1.084 C24 OSC 24 OSC C25 C25 C 0 1 N N R 15.027 -17.834 22.689 -4.459 1.885 -0.115 C25 OSC 25 OSC O26 O26 O 0 1 N N N 17.337 -17.639 22.238 -4.160 -0.244 -1.090 O26 OSC 26 OSC C27 C27 C 0 1 N N N 13.667 -10.386 21.509 6.753 0.822 1.050 C27 OSC 27 OSC C28 C28 C 0 1 Y N N 21.289 -12.979 25.694 -5.765 -3.368 -0.916 C28 OSC 28 OSC C29 C29 C 0 1 Y N N 22.016 -15.064 24.643 -6.600 -1.644 0.520 C29 OSC 29 OSC C30 C30 C 0 1 N N N 14.920 -18.958 23.730 -3.453 2.987 -0.452 C30 OSC 30 OSC O31 O31 O 0 1 N N N 13.984 -16.874 22.899 -5.563 1.954 -1.020 O31 OSC 31 OSC C32 C32 C 0 1 N N N 13.104 -9.760 22.755 7.639 0.504 -0.126 C32 OSC 32 OSC C33 C33 C 0 1 N N N 13.400 -11.667 21.492 6.926 2.061 1.419 C33 OSC 33 OSC C34 C34 C 0 1 Y N N 22.321 -13.801 25.195 -6.810 -2.576 -0.479 C34 OSC 34 OSC C35 C35 C 0 1 Y N N 13.751 -19.849 23.369 -4.084 4.334 -0.208 C35 OSC 35 OSC N36 N36 N 0 1 N N N 12.235 -10.791 23.350 8.401 1.721 -0.436 N36 OSC 36 OSC C37 C37 C 0 1 N N N 12.632 -12.066 22.722 7.954 2.724 0.541 C37 OSC 37 OSC C38 C38 C 0 1 Y N N 13.923 -20.932 22.474 -4.766 4.972 -1.226 C38 OSC 38 OSC C39 C39 C 0 1 Y N N 12.483 -19.595 23.925 -3.975 4.933 1.033 C39 OSC 39 OSC C40 C40 C 0 1 N N N 11.262 -10.605 24.304 9.333 1.888 -1.433 C40 OSC 40 OSC C41 C41 C 0 1 Y N N 12.823 -21.755 22.141 -5.348 6.206 -1.001 C41 OSC 41 OSC C42 C42 C 0 1 Y N N 11.385 -20.415 23.593 -4.554 6.169 1.257 C42 OSC 42 OSC N43 N43 N 0 1 N N N 10.589 -11.687 24.821 9.625 0.896 -2.225 N43 OSC 43 OSC N44 N44 N 0 1 N N N 10.972 -9.403 24.719 9.957 3.103 -1.594 N44 OSC 44 OSC C45 C45 C 0 1 Y N N 11.554 -21.492 22.702 -5.240 6.805 0.240 C45 OSC 45 OSC H2 H2 H 0 1 N N N 19.969 -15.105 21.960 -0.856 -3.996 1.308 H2 OSC 46 OSC H3 H3 H 0 1 N N N 18.510 -11.406 21.870 1.283 -2.019 2.784 H3 OSC 47 OSC H5 H5 H 0 1 N N N 21.153 -12.941 21.574 0.938 -5.228 0.201 H5 OSC 48 OSC H61 1H6 H 0 1 N N N 18.172 -14.767 19.507 -2.063 -2.746 -0.467 H61 OSC 49 OSC H62 2H6 H 0 1 N N N 18.269 -16.104 20.551 -1.509 -4.355 -0.971 H62 OSC 50 OSC H71 1H7 H 0 1 N N N 19.970 -11.321 19.844 2.923 -3.695 1.289 H71 OSC 51 OSC H72 2H7 H 0 1 N N N 19.200 -12.557 19.071 1.626 -4.299 2.373 H72 OSC 52 OSC H9 H9 H 0 1 N N N 18.524 -15.858 23.023 -2.095 -1.390 -0.582 H9 OSC 53 OSC H111 1H11 H 0 0 N N N 22.335 -14.349 20.163 2.000 -2.514 -0.755 H111 OSC 54 OSC H112 2H11 H 0 0 N N N 21.996 -12.979 19.198 2.622 -4.122 -1.186 H112 OSC 55 OSC H12 H12 H 0 1 N N N 19.577 -16.553 18.450 -0.128 -1.713 -1.614 H12 OSC 56 OSC H13 H13 H 0 1 N N N 17.176 -10.026 20.678 3.827 -1.595 2.353 H13 OSC 57 OSC H151 1H15 H 0 0 N N N 18.029 -16.092 25.597 -2.409 -3.098 1.224 H151 OSC 58 OSC H152 2H15 H 0 0 N N N 17.510 -14.485 25.614 -3.030 -1.815 2.291 H152 OSC 59 OSC H16 H16 H 0 1 N N N 15.600 -15.633 23.898 -2.487 0.834 1.269 H16 OSC 60 OSC H171 1H17 H 0 0 N N N 21.609 -15.140 17.883 1.313 -3.183 -3.047 H171 OSC 61 OSC H172 2H17 H 0 0 N N N 20.217 -14.177 17.875 0.486 -4.610 -2.371 H172 OSC 62 OSC H18 H18 H 0 1 N N N 21.586 -17.117 19.483 -0.776 -2.301 -3.740 H18 OSC 63 OSC H191 1H19 H 0 0 N N N 14.811 -11.479 19.323 4.043 0.851 0.956 H191 OSC 64 OSC H192 2H19 H 0 0 N N N 15.480 -10.124 18.567 4.650 -0.451 -0.095 H192 OSC 65 OSC H221 1H22 H 0 0 N N N 13.727 -9.021 19.799 6.232 -1.148 1.683 H221 OSC 66 OSC H222 2H22 H 0 0 N N N 15.005 -8.769 20.886 5.625 0.154 2.734 H222 OSC 67 OSC H23 H23 H 0 1 N N N 19.141 -12.774 26.030 -3.693 -3.846 -0.696 H23 OSC 68 OSC H24 H24 H 0 1 N N N 20.448 -16.493 24.155 -5.181 -0.778 1.865 H24 OSC 69 OSC H25 H25 H 0 1 N N N 14.925 -18.287 21.675 -4.817 2.018 0.906 H25 OSC 70 OSC H28 H28 H 0 1 N N N 21.531 -11.993 26.126 -5.929 -4.096 -1.696 H28 OSC 71 OSC H29 H29 H 0 1 N N N 22.824 -15.707 24.254 -7.416 -1.025 0.861 H29 OSC 72 OSC H301 1H30 H 0 0 N N N 14.852 -18.568 24.772 -2.571 2.879 0.179 H301 OSC 73 OSC H302 2H30 H 0 0 N N N 15.872 -19.528 23.840 -3.162 2.906 -1.499 H302 OSC 74 OSC H31 H31 H 0 1 N N N 13.142 -17.309 22.840 -5.204 1.832 -1.909 H31 OSC 75 OSC H321 1H32 H 0 0 N N N 12.590 -8.787 22.576 7.029 0.213 -0.981 H321 OSC 76 OSC H322 2H32 H 0 0 N N N 13.881 -9.370 23.453 8.326 -0.302 0.135 H322 OSC 77 OSC H33 H33 H 0 1 N N N 13.744 -12.272 20.636 6.408 2.541 2.237 H33 OSC 78 OSC H34 H34 H 0 1 N N N 23.368 -13.456 25.237 -7.791 -2.685 -0.918 H34 OSC 79 OSC H371 1H37 H 0 0 N N N 13.190 -12.751 23.402 8.798 3.058 1.144 H371 OSC 80 OSC H372 2H37 H 0 0 N N N 11.780 -12.756 22.520 7.507 3.573 0.023 H372 OSC 81 OSC H38 H38 H 0 1 N N N 14.915 -21.135 22.036 -4.850 4.504 -2.196 H38 OSC 82 OSC H39 H39 H 0 1 N N N 12.349 -18.751 24.623 -3.439 4.437 1.828 H39 OSC 83 OSC H41 H41 H 0 1 N N N 12.955 -22.600 21.445 -5.885 6.703 -1.796 H41 OSC 84 OSC H42 H42 H 0 1 N N N 10.393 -20.214 24.031 -4.469 6.637 2.227 H42 OSC 85 OSC H43 H43 H 0 1 N N N 9.644 -11.656 24.438 9.184 0.039 -2.112 H43 OSC 86 OSC H441 1H44 H 0 0 N N N 10.741 -8.830 23.908 10.614 3.221 -2.297 H441 OSC 87 OSC H442 2H44 H 0 0 N N N 10.250 -9.265 25.427 9.737 3.843 -1.007 H442 OSC 88 OSC H45 H45 H 0 1 N N N 10.692 -22.130 22.443 -5.693 7.770 0.415 H45 OSC 89 # loop_ _chem_comp_bond.comp_id _chem_comp_bond.atom_id_1 _chem_comp_bond.atom_id_2 _chem_comp_bond.value_order _chem_comp_bond.pdbx_aromatic_flag _chem_comp_bond.pdbx_stereo_config _chem_comp_bond.pdbx_ordinal OSC N1 C2 SING N N 1 OSC N1 C3 SING N N 2 OSC N1 C4 SING N N 3 OSC C2 C5 SING N N 4 OSC C2 C6 SING N N 5 OSC C2 H2 SING N N 6 OSC C3 C7 SING N N 7 OSC C3 C8 SING N N 8 OSC C3 H3 SING N N 9 OSC C4 C9 SING N N 10 OSC C4 O10 DOUB N N 11 OSC C5 C7 SING N N 12 OSC C5 C11 SING N N 13 OSC C5 H5 SING N N 14 OSC C6 C12 SING N N 15 OSC C6 H61 SING N N 16 OSC C6 H62 SING N N 17 OSC C7 H71 SING N N 18 OSC C7 H72 SING N N 19 OSC C8 N13 SING N N 20 OSC C8 O14 DOUB N N 21 OSC C9 C15 SING N N 22 OSC C9 N16 SING N N 23 OSC C9 H9 SING N N 24 OSC C11 C17 SING N N 25 OSC C11 H111 SING N N 26 OSC C11 H112 SING N N 27 OSC C12 C17 SING N N 28 OSC C12 O18 SING N N 29 OSC C12 H12 SING N N 30 OSC N13 C19 SING N N 31 OSC N13 H13 SING N N 32 OSC C15 C20 SING N N 33 OSC C15 H151 SING N N 34 OSC C15 H152 SING N N 35 OSC N16 C21 SING N N 36 OSC N16 H16 SING N N 37 OSC C17 H171 SING N N 38 OSC C17 H172 SING N N 39 OSC O18 H18 SING N N 40 OSC C19 C22 SING N N 41 OSC C19 H191 SING N N 42 OSC C19 H192 SING N N 43 OSC C20 C23 DOUB Y N 44 OSC C20 C24 SING Y N 45 OSC C21 C25 SING N N 46 OSC C21 O26 DOUB N N 47 OSC C22 C27 SING N N 48 OSC C22 H221 SING N N 49 OSC C22 H222 SING N N 50 OSC C23 C28 SING Y N 51 OSC C23 H23 SING N N 52 OSC C24 C29 DOUB Y N 53 OSC C24 H24 SING N N 54 OSC C25 C30 SING N N 55 OSC C25 O31 SING N N 56 OSC C25 H25 SING N N 57 OSC C27 C32 SING N N 58 OSC C27 C33 DOUB N N 59 OSC C28 C34 DOUB Y N 60 OSC C28 H28 SING N N 61 OSC C29 C34 SING Y N 62 OSC C29 H29 SING N N 63 OSC C30 C35 SING N N 64 OSC C30 H301 SING N N 65 OSC C30 H302 SING N N 66 OSC O31 H31 SING N N 67 OSC C32 N36 SING N N 68 OSC C32 H321 SING N N 69 OSC C32 H322 SING N N 70 OSC C33 C37 SING N N 71 OSC C33 H33 SING N N 72 OSC C34 H34 SING N N 73 OSC C35 C38 SING Y N 74 OSC C35 C39 DOUB Y N 75 OSC N36 C37 SING N N 76 OSC N36 C40 SING N N 77 OSC C37 H371 SING N N 78 OSC C37 H372 SING N N 79 OSC C38 C41 DOUB Y N 80 OSC C38 H38 SING N N 81 OSC C39 C42 SING Y N 82 OSC C39 H39 SING N N 83 OSC C40 N43 DOUB N N 84 OSC C40 N44 SING N N 85 OSC C41 C45 SING Y N 86 OSC C41 H41 SING N N 87 OSC C42 C45 DOUB Y N 88 OSC C42 H42 SING N N 89 OSC N43 H43 SING N N 90 OSC N44 H441 SING N N 91 OSC N44 H442 SING N N 92 OSC C45 H45 SING N N 93 # loop_ _pdbx_chem_comp_descriptor.comp_id _pdbx_chem_comp_descriptor.type _pdbx_chem_comp_descriptor.program _pdbx_chem_comp_descriptor.program_version _pdbx_chem_comp_descriptor.descriptor OSC SMILES ACDLabs 10.04 "O=C(NC(C(=O)N1C3CC(O)CCC3CC1C(=O)NCCC2=CCN(C(=[N@H])N)C2)Cc4ccccc4)C(O)Cc5ccccc5" OSC SMILES_CANONICAL CACTVS 3.341 "NC(=N)N1CC=C(CCNC(=O)[C@@H]2C[C@@H]3CC[C@@H](O)C[C@@H]3N2C(=O)[C@@H](Cc4ccccc4)NC(=O)[C@H](O)Cc5ccccc5)C1" OSC SMILES CACTVS 3.341 "NC(=N)N1CC=C(CCNC(=O)[CH]2C[CH]3CC[CH](O)C[CH]3N2C(=O)[CH](Cc4ccccc4)NC(=O)[CH](O)Cc5ccccc5)C1" OSC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)C[C@H](C(=O)N2[C@H]3C[C@@H](CC[C@H]3C[C@H]2C(=O)NCCC4=CCN(C4)C(=N)N)O)NC(=O)[C@@H](Cc5ccccc5)O" OSC SMILES "OpenEye OEToolkits" 1.5.0 "c1ccc(cc1)CC(C(=O)N2C3CC(CCC3CC2C(=O)NCCC4=CCN(C4)C(=N)N)O)NC(=O)C(Cc5ccccc5)O" OSC InChI InChI 1.03 "InChI=1S/C34H44N6O5/c35-34(36)39-16-14-24(21-39)13-15-37-31(43)29-19-25-11-12-26(41)20-28(25)40(29)33(45)27(17-22-7-3-1-4-8-22)38-32(44)30(42)18-23-9-5-2-6-10-23/h1-10,14,25-30,41-42H,11-13,15-21H2,(H3,35,36)(H,37,43)(H,38,44)/t25-,26+,27+,28-,29-,30+/m0/s1" OSC InChIKey InChI 1.03 YNAKQOCSOOKXJP-VCNFNBSBSA-N # loop_ _pdbx_chem_comp_identifier.comp_id _pdbx_chem_comp_identifier.type _pdbx_chem_comp_identifier.program _pdbx_chem_comp_identifier.program_version _pdbx_chem_comp_identifier.identifier OSC "SYSTEMATIC NAME" ACDLabs 10.04 "(2S,3aS,6R,7aS)-N-[2-(1-carbamimidoyl-2,5-dihydro-1H-pyrrol-3-yl)ethyl]-6-hydroxy-1-[(2R)-2-{[(2R)-2-hydroxy-3-phenylpropanoyl]amino}-3-phenylpropanoyl]octahydro-1H-indole-2-carboxamide (non-preferred name)" OSC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S,3aS,6R,7aS)-N-[2-(1-carbamimidoyl-2,5-dihydropyrrol-3-yl)ethyl]-6-hydroxy-1-[(2R)-2-[[(2R)-2-hydroxy-3-phenyl-propanoyl]amino]-3-phenyl-propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxamide" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site OSC "Create component" 2004-01-14 RCSB OSC "Modify descriptor" 2011-06-04 RCSB OSC "Modify synonyms" 2020-05-27 PDBE # loop_ _pdbx_chem_comp_synonyms.ordinal _pdbx_chem_comp_synonyms.comp_id _pdbx_chem_comp_synonyms.name _pdbx_chem_comp_synonyms.provenance _pdbx_chem_comp_synonyms.type 1 OSC OSCILLARIN ? ? 2 OSC "(2R,3AS,6R,7AS)-6-HYDROXY-1-{(2R)-2-[(2R)-2-HYDROXY-3-PHENYL-PROPIONYLAMINO]-3-PHENYL-PROPIONYL}-OCTAHYDORO-INDOLE-2-CARBOXYLIC ACID [2-(1-CARBAMIMIDOYL-2,5-DIHYDRO-1H-PYRROL-3-YL)-ETHYL]-AMIDE" ? ? #