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 
# 
