data_OBN # _chem_comp.id OBN _chem_comp.name OUABAIN _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C29 H44 O12" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 1999-07-08 _chem_comp.pdbx_modified_date 2011-06-04 _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 584.652 _chem_comp.one_letter_code ? _chem_comp.three_letter_code OBN _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 1IBG _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 OBN C1 C1 C 0 1 N N R 6.971 11.837 41.951 0.571 1.426 -1.301 C1 OBN 1 OBN C2 C2 C 0 1 N N N 5.956 11.967 43.068 1.431 0.219 -1.683 C2 OBN 2 OBN C3 C3 C 0 1 N N S 5.424 10.621 43.544 0.553 -0.838 -2.354 C3 OBN 3 OBN C4 C4 C 0 1 N N N 5.039 9.694 42.375 -0.544 -1.280 -1.384 C4 OBN 4 OBN C5 C5 C 0 1 N N S 5.952 9.664 41.111 -1.403 -0.073 -1.003 C5 OBN 5 OBN C6 C6 C 0 1 N N N 5.201 9.017 39.930 -2.482 -0.580 -0.045 C6 OBN 6 OBN C7 C7 C 0 1 N N N 3.869 9.732 39.706 -1.855 -1.136 1.234 C7 OBN 7 OBN C8 C8 C 0 1 N N R 4.156 11.136 39.215 -0.988 -0.058 1.888 C8 OBN 8 OBN C9 C9 C 0 1 N N S 4.977 11.961 40.221 0.109 0.398 0.928 C9 OBN 9 OBN C10 C10 C 0 1 N N R 6.303 11.167 40.690 -0.527 0.986 -0.333 C10 OBN 10 OBN C11 C11 C 0 1 N N R 5.137 13.402 39.633 0.958 1.473 1.614 C11 OBN 11 OBN C12 C12 C 0 1 N N N 3.819 14.064 39.249 1.639 0.852 2.831 C12 OBN 12 OBN C13 C13 C 0 1 N N R 3.065 13.300 38.165 0.601 0.373 3.848 C13 OBN 13 OBN C14 C14 C 0 1 N N S 2.900 11.825 38.633 -0.430 -0.552 3.180 C14 OBN 14 OBN C15 C15 C 0 1 N N N 1.705 11.933 39.561 0.384 -1.875 2.988 C15 OBN 15 OBN C16 C16 C 0 1 N N N 0.873 13.138 39.116 1.228 -1.981 4.279 C16 OBN 16 OBN C17 C17 C 0 1 N N R 1.648 13.870 38.043 1.347 -0.553 4.844 C17 OBN 17 OBN C18 C18 C 0 1 N N N 3.859 13.412 36.863 -0.071 1.548 4.561 C18 OBN 18 OBN C19 C19 C 0 1 N N N 7.371 11.037 39.568 -1.387 2.193 0.045 C19 OBN 19 OBN C20 C20 C 0 1 N N N 0.968 13.847 36.691 0.701 -0.478 6.204 C20 OBN 20 OBN C21 C21 C 0 1 N N N 0.909 15.020 35.767 -0.685 -0.953 6.568 C21 OBN 21 OBN C22 C22 C 0 1 N N N 0.277 12.856 36.079 1.242 0.023 7.311 C22 OBN 22 OBN C23 C23 C 0 1 N N N -0.301 13.327 34.826 0.289 -0.092 8.418 C23 OBN 23 OBN "C1'" "C1'" C 0 1 N N R 5.748 8.991 45.353 -0.211 -1.366 -4.452 "C1'" OBN 24 OBN "C2'" "C2'" C 0 1 N N R 6.918 8.356 46.113 -1.123 -0.917 -5.596 "C2'" OBN 25 OBN "C3'" "C3'" C 0 1 N N R 7.665 9.474 46.885 -0.494 0.296 -6.290 "C3'" OBN 26 OBN "C4'" "C4'" C 0 1 N N R 6.746 10.100 47.939 0.938 -0.063 -6.699 "C4'" OBN 27 OBN "C5'" "C5'" C 0 1 N N S 5.356 10.459 47.376 1.694 -0.574 -5.471 "C5'" OBN 28 OBN "C6'" "C6'" C 0 1 N N N 4.348 10.506 48.518 3.137 -0.902 -5.862 "C6'" OBN 29 OBN O1 O1 O 0 1 N N N 8.127 11.092 42.391 -0.023 1.978 -2.477 O1 OBN 30 OBN O3 O3 O 0 1 N N N 6.290 10.008 44.471 -0.043 -0.287 -3.529 O3 OBN 31 OBN O5 O5 O 0 1 N N N 7.116 8.812 41.382 -2.020 0.440 -2.186 O5 OBN 32 OBN O11 O11 O 0 1 N N N 5.871 14.302 40.454 1.945 1.959 0.703 O11 OBN 33 OBN O14 O14 O 0 1 N N N 2.433 11.051 37.519 -1.506 -0.793 4.088 O14 OBN 34 OBN O19 O19 O 0 1 N N N 8.233 12.191 39.466 -1.981 2.743 -1.132 O19 OBN 35 OBN O21 O21 O 0 1 N N N 0.012 14.614 34.691 -0.847 -0.670 7.986 O21 OBN 36 OBN O23 O23 O 0 1 N N N -1.019 12.769 33.996 0.494 0.279 9.557 O23 OBN 37 OBN "O2'" "O2'" O 0 1 N N N 6.360 7.353 46.995 -1.271 -1.984 -6.536 "O2'" OBN 38 OBN "O3'" "O3'" O 0 1 N N N 8.921 9.067 47.478 -1.257 0.634 -7.449 "O3'" OBN 39 OBN "O4'" "O4'" O 0 1 N N N 7.372 11.331 48.314 1.593 1.097 -7.215 "O4'" OBN 40 OBN "O5'" "O5'" O 0 1 N N N 4.858 9.494 46.394 1.060 -1.749 -4.970 "O5'" OBN 41 OBN H1 H1 H 0 1 N N N 7.320 12.855 41.662 1.197 2.180 -0.822 H1 OBN 42 OBN H21 1H2 H 0 1 N N N 6.372 12.554 43.919 1.886 -0.200 -0.786 H21 OBN 43 OBN H22A 2H2 H 0 0 N N N 5.120 12.643 42.771 2.213 0.534 -2.374 H22A OBN 44 OBN H3 H3 H 0 1 N N N 4.475 10.824 44.093 1.165 -1.698 -2.626 H3 OBN 45 OBN H41 1H4 H 0 1 N N N 4.923 8.654 42.761 -1.168 -2.032 -1.867 H41 OBN 46 OBN H42 2H4 H 0 1 N N N 3.994 9.924 42.060 -0.094 -1.703 -0.486 H42 OBN 47 OBN H61 1H6 H 0 1 N N N 5.821 8.988 39.004 -3.099 -1.348 -0.511 H61 OBN 48 OBN H62 2H6 H 0 1 N N N 5.068 7.918 40.069 -3.101 0.283 0.199 H62 OBN 49 OBN H71 1H7 H 0 1 N N N 3.190 9.169 39.023 -1.237 -2.001 0.989 H71 OBN 50 OBN H72 2H7 H 0 1 N N N 3.218 9.719 40.611 -2.643 -1.437 1.924 H72 OBN 51 OBN H8 H8 H 0 1 N N N 4.838 11.055 38.337 -1.609 0.814 2.088 H8 OBN 52 OBN H9 H9 H 0 1 N N N 4.461 12.102 41.199 0.738 -0.450 0.659 H9 OBN 53 OBN H11 H11 H 0 1 N N N 5.731 13.209 38.709 0.318 2.296 1.933 H11 OBN 54 OBN H121 1H12 H 0 0 N N N 3.175 14.222 40.146 2.243 0.003 2.509 H121 OBN 55 OBN H122 2H12 H 0 0 N N N 3.978 15.126 38.950 2.285 1.594 3.299 H122 OBN 56 OBN H151 1H15 H 0 0 N N N 1.109 10.991 39.610 1.029 -1.801 2.113 H151 OBN 57 OBN H152 2H15 H 0 0 N N N 1.995 11.981 40.636 -0.288 -2.728 2.899 H152 OBN 58 OBN H161 1H16 H 0 0 N N N -0.154 12.855 38.789 2.218 -2.374 4.047 H161 OBN 59 OBN H162 2H16 H 0 0 N N N 0.582 13.799 39.965 0.729 -2.628 5.000 H162 OBN 60 OBN H17 H17 H 0 1 N N N 1.694 14.976 38.175 2.396 -0.263 4.912 H17 OBN 61 OBN H181 1H18 H 0 0 N N N 3.307 12.853 36.070 0.661 2.067 5.178 H181 OBN 62 OBN H182 2H18 H 0 0 N N N 4.069 14.468 36.577 -0.477 2.238 3.821 H182 OBN 63 OBN H183 3H18 H 0 0 N N N 4.915 13.072 36.972 -0.879 1.176 5.192 H183 OBN 64 OBN H191 1H19 H 0 0 N N N 7.969 10.105 39.696 -2.170 1.880 0.735 H191 OBN 65 OBN H192 2H19 H 0 0 N N N 6.890 10.813 38.587 -0.763 2.949 0.523 H192 OBN 66 OBN H211 1H21 H 0 0 N N N 0.611 15.971 36.265 -1.436 -0.416 5.990 H211 OBN 67 OBN H212 2H21 H 0 0 N N N 1.908 15.365 35.413 -0.768 -2.025 6.388 H212 OBN 68 OBN H22 H22 H 0 1 N N N 0.199 11.848 36.520 2.232 0.450 7.383 H22 OBN 69 OBN "H1'" "H1'" H 0 1 N N N 5.171 8.300 44.694 -0.664 -2.214 -3.938 "H1'" OBN 70 OBN "H2'" "H2'" H 0 1 N N N 7.656 7.866 45.436 -2.100 -0.644 -5.198 "H2'" OBN 71 OBN "H3'" "H3'" H 0 1 N N N 7.938 10.234 46.116 -0.478 1.142 -5.603 "H3'" OBN 72 OBN "H4'" "H4'" H 0 1 N N N 6.602 9.376 48.775 0.915 -0.838 -7.465 "H4'" OBN 73 OBN "H5'" "H5'" H 0 1 N N N 5.470 11.444 46.868 1.694 0.194 -4.699 "H5'" OBN 74 OBN "H6'1" "1H6'" H 0 0 N N N 3.342 10.765 48.110 3.677 -1.265 -4.987 "H6'1" OBN 75 OBN "H6'2" "2H6'" H 0 0 N N N 4.333 9.560 49.108 3.138 -1.672 -6.634 "H6'2" OBN 76 OBN "H6'3" "3H6'" H 0 0 N N N 4.665 11.196 49.333 3.623 -0.004 -6.243 "H6'3" OBN 77 OBN HO1 HO1 H 0 1 N N N 8.763 11.010 41.690 0.700 2.208 -3.075 HO1 OBN 78 OBN HO5 HO5 H 0 1 N N N 7.672 8.793 40.612 -2.516 -0.289 -2.582 HO5 OBN 79 OBN HOE HOE H 0 1 N N N 5.968 15.177 40.097 2.455 2.631 1.175 HOE OBN 80 OBN HOF HOF H 0 1 N N N 1.661 11.474 37.161 -2.069 -1.466 3.682 HOF OBN 81 OBN HON HON H 0 1 N N N 8.885 12.111 38.780 -2.513 3.499 -0.850 HON OBN 82 OBN "HO2'" "'HO2" H 0 0 N N N 7.085 6.959 47.466 -1.663 -2.726 -6.056 "HO2'" OBN 83 OBN "HO3'" "'HO3" H 0 0 N N N 9.378 9.752 47.951 -2.151 0.839 -7.145 "HO3'" OBN 84 OBN "HO4'" "'HO4" H 0 0 N N N 6.802 11.719 48.967 2.489 0.827 -7.459 "HO4'" OBN 85 # 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 OBN C1 C2 SING N N 1 OBN C1 C10 SING N N 2 OBN C1 O1 SING N N 3 OBN C1 H1 SING N N 4 OBN C2 C3 SING N N 5 OBN C2 H21 SING N N 6 OBN C2 H22A SING N N 7 OBN C3 C4 SING N N 8 OBN C3 O3 SING N N 9 OBN C3 H3 SING N N 10 OBN C4 C5 SING N N 11 OBN C4 H41 SING N N 12 OBN C4 H42 SING N N 13 OBN C5 C6 SING N N 14 OBN C5 C10 SING N N 15 OBN C5 O5 SING N N 16 OBN C6 C7 SING N N 17 OBN C6 H61 SING N N 18 OBN C6 H62 SING N N 19 OBN C7 C8 SING N N 20 OBN C7 H71 SING N N 21 OBN C7 H72 SING N N 22 OBN C8 C9 SING N N 23 OBN C8 C14 SING N N 24 OBN C8 H8 SING N N 25 OBN C9 C10 SING N N 26 OBN C9 C11 SING N N 27 OBN C9 H9 SING N N 28 OBN C10 C19 SING N N 29 OBN C11 C12 SING N N 30 OBN C11 O11 SING N N 31 OBN C11 H11 SING N N 32 OBN C12 C13 SING N N 33 OBN C12 H121 SING N N 34 OBN C12 H122 SING N N 35 OBN C13 C14 SING N N 36 OBN C13 C17 SING N N 37 OBN C13 C18 SING N N 38 OBN C14 C15 SING N N 39 OBN C14 O14 SING N N 40 OBN C15 C16 SING N N 41 OBN C15 H151 SING N N 42 OBN C15 H152 SING N N 43 OBN C16 C17 SING N N 44 OBN C16 H161 SING N N 45 OBN C16 H162 SING N N 46 OBN C17 C20 SING N N 47 OBN C17 H17 SING N N 48 OBN C18 H181 SING N N 49 OBN C18 H182 SING N N 50 OBN C18 H183 SING N N 51 OBN C19 O19 SING N N 52 OBN C19 H191 SING N N 53 OBN C19 H192 SING N N 54 OBN C20 C21 SING N N 55 OBN C20 C22 DOUB N N 56 OBN C21 O21 SING N N 57 OBN C21 H211 SING N N 58 OBN C21 H212 SING N N 59 OBN C22 C23 SING N N 60 OBN C22 H22 SING N N 61 OBN C23 O21 SING N N 62 OBN C23 O23 DOUB N N 63 OBN "C1'" "C2'" SING N N 64 OBN "C1'" O3 SING N N 65 OBN "C1'" "O5'" SING N N 66 OBN "C1'" "H1'" SING N N 67 OBN "C2'" "C3'" SING N N 68 OBN "C2'" "O2'" SING N N 69 OBN "C2'" "H2'" SING N N 70 OBN "C3'" "C4'" SING N N 71 OBN "C3'" "O3'" SING N N 72 OBN "C3'" "H3'" SING N N 73 OBN "C4'" "C5'" SING N N 74 OBN "C4'" "O4'" SING N N 75 OBN "C4'" "H4'" SING N N 76 OBN "C5'" "C6'" SING N N 77 OBN "C5'" "O5'" SING N N 78 OBN "C5'" "H5'" SING N N 79 OBN "C6'" "H6'1" SING N N 80 OBN "C6'" "H6'2" SING N N 81 OBN "C6'" "H6'3" SING N N 82 OBN O1 HO1 SING N N 83 OBN O5 HO5 SING N N 84 OBN O11 HOE SING N N 85 OBN O14 HOF SING N N 86 OBN O19 HON SING N N 87 OBN "O2'" "HO2'" SING N N 88 OBN "O3'" "HO3'" SING N N 89 OBN "O4'" "HO4'" SING N N 90 # 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 OBN SMILES ACDLabs 10.04 "O=C1OCC(=C1)C4CCC5(O)C3CCC6(O)CC(OC2OC(C(O)C(O)C2O)C)CC(O)C6(CO)C3C(O)CC45C" OBN SMILES_CANONICAL CACTVS 3.341 "C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C6=CC(=O)OC6)[C@H](O)[C@H](O)[C@H]1O" OBN SMILES CACTVS 3.341 "C[CH]1O[CH](O[CH]2C[CH](O)[C]3(CO)[CH]4[CH](O)C[C]5(C)[CH](CC[C]5(O)[CH]4CC[C]3(O)C2)C6=CC(=O)OC6)[CH](O)[CH](O)[CH]1O" OBN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O" OBN SMILES "OpenEye OEToolkits" 1.5.0 "CC1C(C(C(C(O1)OC2CC(C3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O" OBN InChI InChI 1.03 ;InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1 ; OBN InChIKey InChI 1.03 LPMXVESGRSUGHW-HBYQJFLCSA-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 OBN "SYSTEMATIC NAME" ACDLabs 10.04 "(1alpha,3beta,5beta,11alpha,17alpha)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide" OBN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site OBN "Create component" 1999-07-08 RCSB OBN "Modify descriptor" 2011-06-04 RCSB #