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                    2008-10-14 
_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 InChI            InChI                1.02b 
;InChI=1/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/f/h35,37-38H,36H2
;
OSC InChIKey         InChI                1.02b YNAKQOCSOOKXJP-IOSCKGTBDA 
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 
# 
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 
# 
