data_8I1 # _chem_comp.id 8I1 _chem_comp.name "2-(5-{[(2R)-2-amino-3-phenylpropyl]oxy}pyridin-3-yl)-8,9-dimethoxybenzo[c][2,7]naphthyridin-4-amine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C28 H27 N5 O3" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-08-17 _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 481.546 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 8I1 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 3IOP _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 8I1 C1 C1 C 0 1 N N N -35.016 -22.117 5.778 -5.584 3.755 -0.021 C1 8I1 1 8I1 N1 N1 N 0 1 Y N N -34.409 -29.392 3.312 -0.952 -1.872 0.007 N1 8I1 2 8I1 O1 O1 O 0 1 N N N -33.673 -22.333 6.213 -6.702 2.866 -0.032 O1 8I1 3 8I1 C2 C2 C 0 1 Y N N -32.985 -23.456 5.808 -6.431 1.533 -0.033 C2 8I1 4 8I1 N2 N2 N 0 1 Y N N -30.607 -26.687 4.676 -5.639 -2.525 -0.034 N2 8I1 5 8I1 O2 O2 O 0 1 N N N -31.053 -22.243 6.438 -8.767 1.051 -0.053 O2 8I1 6 8I1 C3 C3 C 0 1 Y N N -33.582 -24.621 5.301 -5.122 1.100 -0.024 C3 8I1 7 8I1 N3 N3 N 0 1 N N N -32.264 -30.304 3.092 -1.773 -4.065 -0.005 N3 8I1 8 8I1 O3 O3 O 0 1 N N N -39.720 -26.670 3.014 3.750 0.087 0.053 O3 8I1 9 8I1 C4 C4 C 0 1 Y N N -32.826 -25.758 4.896 -4.846 -0.268 -0.025 C4 8I1 10 8I1 N4 N4 N 0 1 Y N N -38.583 -30.210 3.200 1.063 2.469 0.032 N4 8I1 11 8I1 C5 C5 C 0 1 Y N N -33.389 -26.977 4.365 -3.475 -0.779 -0.014 C5 8I1 12 8I1 N5 N5 N 0 1 N N N -40.992 -24.277 2.459 6.286 -0.477 1.332 N5 8I1 13 8I1 C6 C6 C 0 1 Y N N -34.777 -27.191 4.174 -2.351 0.044 -0.002 C6 8I1 14 8I1 C7 C7 C 0 1 Y N N -35.259 -28.394 3.653 -1.094 -0.548 0.008 C7 8I1 15 8I1 C8 C8 C 0 1 Y N N -33.072 -29.233 3.473 -1.983 -2.697 -0.004 C8 8I1 16 8I1 C9 C9 C 0 1 Y N N -32.524 -28.038 4.002 -3.295 -2.185 -0.015 C9 8I1 17 8I1 C10 C10 C 0 1 Y N N -31.154 -27.816 4.184 -4.430 -3.016 -0.026 C10 8I1 18 8I1 C11 C11 C 0 1 Y N N -31.419 -25.682 5.025 -5.904 -1.208 -0.035 C11 8I1 19 8I1 C12 C12 C 0 1 Y N N -30.830 -24.526 5.534 -7.227 -0.744 -0.044 C12 8I1 20 8I1 C13 C13 C 0 1 Y N N -31.582 -23.409 5.929 -7.482 0.609 -0.044 C13 8I1 21 8I1 C14 C14 C 0 1 N N N -29.656 -22.147 6.709 -9.795 0.058 -0.064 C14 8I1 22 8I1 C15 C15 C 0 1 Y N N -36.698 -28.663 3.447 0.113 0.313 0.021 C15 8I1 23 8I1 C16 C16 C 0 1 Y N N -37.617 -27.606 3.314 1.390 -0.256 0.031 C16 8I1 24 8I1 C17 C17 C 0 1 Y N N -38.986 -27.822 3.125 2.488 0.593 0.042 C17 8I1 25 8I1 C18 C18 C 0 1 Y N N -39.416 -29.143 3.080 2.282 1.966 0.042 C18 8I1 26 8I1 C19 C19 C 0 1 Y N N -37.257 -29.947 3.384 -0.007 1.701 0.021 C19 8I1 27 8I1 C20 C20 C 0 1 N N N -41.108 -26.713 2.662 4.826 1.026 0.064 C20 8I1 28 8I1 C21 C21 C 0 1 N N R -41.777 -25.390 3.076 6.159 0.275 0.076 C21 8I1 29 8I1 C22 C22 C 0 1 N N N -41.884 -25.104 4.596 7.310 1.277 -0.038 C22 8I1 30 8I1 C23 C23 C 0 1 Y N N -41.394 -26.209 5.504 8.615 0.532 -0.150 C23 8I1 31 8I1 C24 C24 C 0 1 Y N N -40.087 -26.172 6.030 9.105 0.179 -1.394 C24 8I1 32 8I1 C25 C25 C 0 1 Y N N -39.629 -27.203 6.855 10.302 -0.504 -1.497 C25 8I1 33 8I1 C26 C26 C 0 1 Y N N -40.469 -28.274 7.171 11.009 -0.835 -0.356 C26 8I1 34 8I1 C27 C27 C 0 1 Y N N -41.768 -28.322 6.656 10.520 -0.482 0.887 C27 8I1 35 8I1 C28 C28 C 0 1 Y N N -42.234 -27.294 5.827 9.325 0.206 0.990 C28 8I1 36 8I1 H1 H1 H 0 1 N N N -35.393 -21.175 6.203 -5.939 4.786 -0.022 H1 8I1 37 8I1 H1A H1A H 0 1 N N N -35.041 -22.060 4.680 -4.987 3.577 0.873 H1A 8I1 38 8I1 H1B H1B H 0 1 N N N -35.649 -22.950 6.116 -4.972 3.582 -0.906 H1B 8I1 39 8I1 H3 H3 H 0 1 N N N -34.658 -24.656 5.215 -4.314 1.816 -0.016 H3 8I1 40 8I1 HN3 HN3 H 0 1 N N N -32.836 -31.048 2.746 -0.870 -4.418 0.004 HN3 8I1 41 8I1 HN3A HN3A H 0 0 N N N -31.634 -30.007 2.374 -2.531 -4.672 -0.013 HN3A 8I1 42 8I1 HN5 HN5 H 0 1 N N N -41.402 -23.400 2.710 6.257 0.142 2.128 HN5 8I1 43 8I1 HN5A HN5A H 0 0 N N N -40.049 -24.311 2.791 5.575 -1.189 1.400 HN5A 8I1 44 8I1 H6 H6 H 0 1 N N N -35.475 -26.410 4.436 -2.454 1.119 -0.001 H6 8I1 45 8I1 H10 H10 H 0 1 N N N -30.481 -28.614 3.908 -4.297 -4.088 -0.026 H10 8I1 46 8I1 H12 H12 H 0 1 N N N -29.755 -24.488 5.628 -8.046 -1.448 -0.052 H12 8I1 47 8I1 H14 H14 H 0 1 N N N -29.427 -21.148 7.107 -10.770 0.545 -0.070 H14 8I1 48 8I1 H14A H14A H 0 0 N N N -29.373 -22.910 7.449 -9.692 -0.562 -0.954 H14A 8I1 49 8I1 H14B H14B H 0 0 N N N -29.090 -22.310 5.780 -9.706 -0.566 0.826 H14B 8I1 50 8I1 H16 H16 H 0 1 N N N -37.252 -26.591 3.360 1.518 -1.329 0.031 H16 8I1 51 8I1 H18 H18 H 0 1 N N N -40.470 -29.332 2.942 3.133 2.632 0.051 H18 8I1 52 8I1 H19 H19 H 0 1 N N N -36.589 -30.789 3.489 -0.988 2.152 0.013 H19 8I1 53 8I1 H20 H20 H 0 1 N N N -41.208 -26.852 1.575 4.770 1.653 -0.825 H20 8I1 54 8I1 H20A H20A H 0 0 N N N -41.594 -27.551 3.184 4.753 1.651 0.955 H20A 8I1 55 8I1 H21 H21 H 0 1 N N N -42.817 -25.471 2.727 6.194 -0.416 -0.766 H21 8I1 56 8I1 H22 H22 H 0 1 N N N -41.279 -24.210 4.807 7.167 1.895 -0.924 H22 8I1 57 8I1 H22A H22A H 0 0 N N N -42.946 -24.933 4.826 7.328 1.911 0.848 H22A 8I1 58 8I1 H24 H24 H 0 1 N N N -39.436 -25.343 5.794 8.552 0.438 -2.285 H24 8I1 59 8I1 H25 H25 H 0 1 N N N -38.624 -27.172 7.249 10.684 -0.780 -2.469 H25 8I1 60 8I1 H26 H26 H 0 1 N N N -40.114 -29.066 7.814 11.944 -1.370 -0.437 H26 8I1 61 8I1 H27 H27 H 0 1 N N N -42.413 -29.154 6.898 11.072 -0.740 1.778 H27 8I1 62 8I1 H28 H28 H 0 1 N N N -43.239 -27.333 5.434 8.944 0.485 1.961 H28 8I1 63 # 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 8I1 C1 O1 SING N N 1 8I1 N1 C7 DOUB Y N 2 8I1 N1 C8 SING Y N 3 8I1 O1 C2 SING N N 4 8I1 C2 C3 DOUB Y N 5 8I1 C2 C13 SING Y N 6 8I1 N2 C10 DOUB Y N 7 8I1 N2 C11 SING Y N 8 8I1 O2 C13 SING N N 9 8I1 O2 C14 SING N N 10 8I1 C3 C4 SING Y N 11 8I1 N3 C8 SING N N 12 8I1 O3 C17 SING N N 13 8I1 O3 C20 SING N N 14 8I1 C4 C5 SING Y N 15 8I1 C4 C11 DOUB Y N 16 8I1 N4 C18 DOUB Y N 17 8I1 N4 C19 SING Y N 18 8I1 C5 C6 DOUB Y N 19 8I1 C5 C9 SING Y N 20 8I1 N5 C21 SING N N 21 8I1 C6 C7 SING Y N 22 8I1 C7 C15 SING Y N 23 8I1 C8 C9 DOUB Y N 24 8I1 C9 C10 SING Y N 25 8I1 C11 C12 SING Y N 26 8I1 C12 C13 DOUB Y N 27 8I1 C15 C16 SING Y N 28 8I1 C15 C19 DOUB Y N 29 8I1 C16 C17 DOUB Y N 30 8I1 C17 C18 SING Y N 31 8I1 C20 C21 SING N N 32 8I1 C21 C22 SING N N 33 8I1 C22 C23 SING N N 34 8I1 C23 C24 DOUB Y N 35 8I1 C23 C28 SING Y N 36 8I1 C24 C25 SING Y N 37 8I1 C25 C26 DOUB Y N 38 8I1 C26 C27 SING Y N 39 8I1 C27 C28 DOUB Y N 40 8I1 C1 H1 SING N N 41 8I1 C1 H1A SING N N 42 8I1 C1 H1B SING N N 43 8I1 C3 H3 SING N N 44 8I1 N3 HN3 SING N N 45 8I1 N3 HN3A SING N N 46 8I1 N5 HN5 SING N N 47 8I1 N5 HN5A SING N N 48 8I1 C6 H6 SING N N 49 8I1 C10 H10 SING N N 50 8I1 C12 H12 SING N N 51 8I1 C14 H14 SING N N 52 8I1 C14 H14A SING N N 53 8I1 C14 H14B SING N N 54 8I1 C16 H16 SING N N 55 8I1 C18 H18 SING N N 56 8I1 C19 H19 SING N N 57 8I1 C20 H20 SING N N 58 8I1 C20 H20A SING N N 59 8I1 C21 H21 SING N N 60 8I1 C22 H22 SING N N 61 8I1 C22 H22A SING N N 62 8I1 C24 H24 SING N N 63 8I1 C25 H25 SING N N 64 8I1 C26 H26 SING N N 65 8I1 C27 H27 SING N N 66 8I1 C28 H28 SING N N 67 # 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 8I1 SMILES ACDLabs 11.02 "n2c1cc(OC)c(OC)cc1c5c(c2)c(nc(c4cc(OCC(N)Cc3ccccc3)cnc4)c5)N" 8I1 SMILES_CANONICAL CACTVS 3.352 "COc1cc2ncc3c(N)nc(cc3c2cc1OC)c4cncc(OC[C@H](N)Cc5ccccc5)c4" 8I1 SMILES CACTVS 3.352 "COc1cc2ncc3c(N)nc(cc3c2cc1OC)c4cncc(OC[CH](N)Cc5ccccc5)c4" 8I1 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "COc1cc2c3cc(nc(c3cnc2cc1OC)N)c4cc(cnc4)OC[C@@H](Cc5ccccc5)N" 8I1 SMILES "OpenEye OEToolkits" 1.7.0 "COc1cc2c3cc(nc(c3cnc2cc1OC)N)c4cc(cnc4)OCC(Cc5ccccc5)N" 8I1 InChI InChI 1.03 "InChI=1S/C28H27N5O3/c1-34-26-11-22-21-10-24(33-28(30)23(21)15-32-25(22)12-27(26)35-2)18-9-20(14-31-13-18)36-16-19(29)8-17-6-4-3-5-7-17/h3-7,9-15,19H,8,16,29H2,1-2H3,(H2,30,33)/t19-/m1/s1" 8I1 InChIKey InChI 1.03 XNXUJUXYVTYIGP-LJQANCHMSA-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 8I1 "SYSTEMATIC NAME" ACDLabs 11.02 "2-(5-{[(2R)-2-amino-3-phenylpropyl]oxy}pyridin-3-yl)-8,9-dimethoxybenzo[c][2,7]naphthyridin-4-amine" 8I1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "2-[5-[(2R)-2-azanyl-3-phenyl-propoxy]pyridin-3-yl]-8,9-dimethoxy-benzo[f][2,7]naphthyridin-4-amine" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 8I1 "Create component" 2009-08-17 RCSB 8I1 "Modify aromatic_flag" 2011-06-04 RCSB 8I1 "Modify descriptor" 2011-06-04 RCSB #