data_Q22
# 
_chem_comp.id                                    Q22 
_chem_comp.name                                  (4aS)-5-[(2,4-diaminopteridin-6-yl)methyl]-4a,5-dihydro-2H-dibenzo[b,f]azepin-8-ol 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H19 N7 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-09-09 
_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                        385.422 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     Q22 
_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        3D80 
_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 
Q22 C7*  "C7'"  C 0 1 Y N N -4.187  3.413  15.277 -1.671 1.327  -1.161 C7*  Q22 1  
Q22 N8*  "N8'"  N 0 1 Y N N -3.320  4.366  15.067 -2.941 1.606  -0.960 N8*  Q22 2  
Q22 C8   C8     C 0 1 Y N N -2.116  4.122  14.537 -3.750 0.669  -0.459 C8   Q22 3  
Q22 N1*  "N1'"  N 0 1 Y N N -1.233  5.099  14.304 -5.050 0.901  -0.235 N1*  Q22 4  
Q22 C2*  "C2'"  C 0 1 Y N N -0.036  4.835  13.771 -5.833 -0.036 0.261  C2*  Q22 5  
Q22 N2*  "N2'"  N 0 1 N N N 0.836   5.783  13.574 -7.165 0.267  0.469  N2*  Q22 6  
Q22 N3*  "N3'"  N 0 1 Y N N 0.265   3.607  13.366 -5.410 -1.257 0.570  N3*  Q22 7  
Q22 C4*  "C4'"  C 0 1 Y N N -0.582  2.601  13.563 -4.144 -1.612 0.395  C4*  Q22 8  
Q22 N4*  "N4'"  N 0 1 N N N -0.269  1.383  13.186 -3.708 -2.879 0.716  N4*  Q22 9  
Q22 C4   C4     C 0 1 Y N N -1.822  2.839  14.140 -3.227 -0.611 -0.152 C4   Q22 10 
Q22 N5*  "N5'"  N 0 1 Y N N -2.710  1.859  14.342 -1.940 -0.873 -0.363 N5*  Q22 11 
Q22 C6*  "C6'"  C 0 1 Y N N -3.904  2.113  14.885 -1.161 0.065  -0.858 C6*  Q22 12 
Q22 C9*  "C9'"  C 0 1 N N N -4.859  0.893  15.129 0.298  -0.227 -1.099 C9*  Q22 13 
Q22 N*0  "N'0"  N 0 1 N N N -6.307  1.110  15.305 1.053  -0.007 0.142  N*0  Q22 14 
Q22 C*0  "C'0"  C 0 1 N N S -7.107  0.236  16.209 1.259  1.425  0.386  C*0  Q22 15 
Q22 C*1  "C'1"  C 0 1 N N N -6.439  -0.999 16.803 1.502  1.646  1.849  C*1  Q22 16 
Q22 C*2  "C'2"  C 0 1 N N N -6.713  -1.450 18.077 2.381  2.477  2.312  C*2  Q22 17 
Q22 C*3  "C'3"  C 0 1 N N N -7.487  -0.693 18.935 3.257  3.319  1.436  C*3  Q22 18 
Q22 C*4  "C'4"  C 0 1 N N N -8.094  0.474  18.512 3.290  2.796  0.034  C*4  Q22 19 
Q22 C*5  "C'5"  C 0 1 N N N -7.889  1.002  17.258 2.389  1.950  -0.443 C*5  Q22 20 
Q22 C*6  "C'6"  C 0 1 N N N -8.500  2.216  17.069 2.486  1.520  -1.850 C*6  Q22 21 
Q22 C6   C6     C 0 1 N N N -8.573  2.926  15.892 2.813  0.236  -2.109 C6   Q22 22 
Q22 C*7  "C'7"  C 0 1 Y N N -8.100  2.495  14.676 3.114  -0.651 -0.975 C*7  Q22 23 
Q22 C*8  "C'8"  C 0 1 Y N N -8.888  2.977  13.641 4.278  -1.424 -0.990 C*8  Q22 24 
Q22 C7   C7     C 0 1 Y N N -7.023  1.689  14.423 2.249  -0.724 0.133  C7   Q22 25 
Q22 C9   C9     C 0 1 Y N N -6.733  1.295  13.130 2.586  -1.521 1.215  C9   Q22 26 
Q22 C11  C11    C 0 1 Y N N -7.510  1.788  12.092 3.748  -2.268 1.196  C11  Q22 27 
Q22 C*9  "C'9"  C 0 1 Y N N -8.591  2.620  12.329 4.589  -2.228 0.091  C*9  Q22 28 
Q22 O1   O1     O 0 1 N N N -9.337  3.113  11.311 5.720  -2.982 0.073  O1   Q22 29 
Q22 H7*  "H7'"  H 0 1 N N N -5.128  3.638  15.758 -1.017 2.083  -1.570 H7*  Q22 30 
Q22 HN2* "HN2'" H 0 0 N N N 1.059   6.218  14.446 -7.501 1.151  0.251  HN2* Q22 31 
Q22 HN2A HN2A   H 0 0 N N N 1.666   5.394  13.173 -7.764 -0.404 0.832  HN2A Q22 32 
Q22 HN4* "HN4'" H 0 0 N N N -0.189  1.352  12.190 -4.331 -3.529 1.078  HN4* Q22 33 
Q22 HN4A HN4A   H 0 0 N N N 0.603   1.120  13.598 -2.778 -3.121 0.581  HN4A Q22 34 
Q22 H9*  "H9'"  H 0 1 N N N -4.754  0.243  14.248 0.413  -1.264 -1.415 H9*  Q22 35 
Q22 H9*A "H9'A" H 0 0 N N N -4.536  0.503  16.106 0.677  0.435  -1.877 H9*A Q22 36 
Q22 H*0  "H'0"  H 0 1 N N N -7.810  -0.195 15.482 0.355  1.962  0.097  H*0  Q22 37 
Q22 H*1  "H'1"  H 0 1 N N N -5.724  -1.542 16.203 0.911  1.082  2.556  H*1  Q22 38 
Q22 H*2  "H'2"  H 0 1 N N N -6.320  -2.401 18.406 2.487  2.568  3.383  H*2  Q22 39 
Q22 H*3  "H'3"  H 0 1 N N N -8.305  -1.353 19.260 2.876  4.341  1.427  H*3  Q22 40 
Q22 H*3A "H'3A" H 0 0 N N N -6.757  -0.337 19.677 4.269  3.321  1.840  H*3A Q22 41 
Q22 H*4  "H'4"  H 0 1 N N N -8.755  0.992  19.192 4.085  3.123  -0.620 H*4  Q22 42 
Q22 H6   H6     H 0 1 N N N -9.039  3.900  15.927 2.853  -0.130 -3.124 H6   Q22 43 
Q22 H*8  "H'8"  H 0 1 N N N -9.726  3.625  13.852 4.936  -1.394 -1.847 H*8  Q22 44 
Q22 H9   H9     H 0 1 N N N -5.917  0.616  12.932 1.937  -1.559 2.078  H9   Q22 45 
Q22 H11  H11    H 0 1 N N N -7.266  1.517  11.076 4.004  -2.886 2.044  H11  Q22 46 
Q22 HO1  HO1    H 0 1 N N N -10.234 3.228  11.602 6.497  -2.534 0.434  HO1  Q22 47 
Q22 H19  H19    H 0 1 N N N -8.972  2.660  17.933 2.298  2.216  -2.655 H19  Q22 48 
# 
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 
Q22 C7* N8*  DOUB Y N 1  
Q22 C7* C6*  SING Y N 2  
Q22 C7* H7*  SING N N 3  
Q22 N8* C8   SING Y N 4  
Q22 C8  N1*  DOUB Y N 5  
Q22 C8  C4   SING Y N 6  
Q22 N1* C2*  SING Y N 7  
Q22 C2* N2*  SING N N 8  
Q22 C2* N3*  DOUB Y N 9  
Q22 N2* HN2* SING N N 10 
Q22 N2* HN2A SING N N 11 
Q22 N3* C4*  SING Y N 12 
Q22 C4* N4*  SING N N 13 
Q22 C4* C4   DOUB Y N 14 
Q22 N4* HN4* SING N N 15 
Q22 N4* HN4A SING N N 16 
Q22 C4  N5*  SING Y N 17 
Q22 N5* C6*  DOUB Y N 18 
Q22 C6* C9*  SING N N 19 
Q22 C9* N*0  SING N N 20 
Q22 C9* H9*  SING N N 21 
Q22 C9* H9*A SING N N 22 
Q22 N*0 C*0  SING N N 23 
Q22 N*0 C7   SING N N 24 
Q22 C*0 C*1  SING N N 25 
Q22 C*0 C*5  SING N N 26 
Q22 C*0 H*0  SING N N 27 
Q22 C*1 C*2  DOUB N N 28 
Q22 C*1 H*1  SING N N 29 
Q22 C*2 C*3  SING N N 30 
Q22 C*2 H*2  SING N N 31 
Q22 C*3 C*4  SING N N 32 
Q22 C*3 H*3  SING N N 33 
Q22 C*3 H*3A SING N N 34 
Q22 C*4 C*5  DOUB N N 35 
Q22 C*4 H*4  SING N N 36 
Q22 C*5 C*6  SING N N 37 
Q22 C*6 C6   DOUB N N 38 
Q22 C6  C*7  SING N N 39 
Q22 C6  H6   SING N N 40 
Q22 C*7 C*8  DOUB N N 41 
Q22 C*7 C7   SING Y N 42 
Q22 C*8 C*9  SING Y N 43 
Q22 C*8 H*8  SING Y N 44 
Q22 C7  C9   DOUB N N 45 
Q22 C9  C11  SING Y N 46 
Q22 C9  H9   SING Y N 47 
Q22 C11 C*9  DOUB N N 48 
Q22 C11 H11  SING Y N 49 
Q22 C*9 O1   SING N N 50 
Q22 O1  HO1  SING N N 51 
Q22 C*6 H19  SING N N 52 
# 
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 
Q22 SMILES           ACDLabs              10.04 Oc1cc2c(cc1)N(C3C=CCC=C3C=C2)Cc4nc5c(nc4)nc(nc5N)N                                                                                                                            
Q22 InChI            InChI                1.02b InChI=1/C21H19N7O/c22-19-18-20(27-21(23)26-19)24-10-14(25-18)11-28-16-4-2-1-3-12(16)5-6-13-9-15(29)7-8-17(13)28/h2-10,16,29H,1,11H2,(H4,22,23,24,26,27)/t16-/m0/s1/f/h22-23H2 
Q22 InChIKey         InChI                1.02b PCBWLKUEKANDCL-OCPZEHGYDZ                                                                                                                                                     
Q22 SMILES_CANONICAL CACTVS               3.341 Nc1nc(N)c2nc(CN3[C@H]4C=CCC=C4C=Cc5cc(O)ccc35)cnc2n1                                                                                                                          
Q22 SMILES           CACTVS               3.341 Nc1nc(N)c2nc(CN3[CH]4C=CCC=C4C=Cc5cc(O)ccc35)cnc2n1                                                                                                                           
Q22 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1O)C=CC3=CCC=C[C@@H]3[N@]2Cc4cnc5c(n4)c(nc(n5)N)N                                                                                                                    
Q22 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1O)C=CC3=CCC=CC3N2Cc4cnc5c(n4)c(nc(n5)N)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 
Q22 "SYSTEMATIC NAME" ACDLabs              10.04 (4aS)-5-[(2,4-diaminopteridin-6-yl)methyl]-4a,5-dihydro-2H-dibenzo[b,f]azepin-8-ol       
Q22 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (10aS,11R)-11-[(2,4-diaminopteridin-6-yl)methyl]-8,10a-dihydrobenzo[b][1]benzazepin-3-ol 
# 
