data_PFH
# 
_chem_comp.id                                    PFH 
_chem_comp.name                                  6,7-DIMETHOXY-4-[(3R)-3-(2-NAPHTHYLOXY)PYRROLIDIN-1-YL]QUINAZOLINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C24 H23 N3 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-02-21 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        401.458 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PFH 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
PFH C4   C4   C 0 1 Y N N 14.030 16.049 44.500 -2.970 0.443  -7.088 C4   PFH 1  
PFH C7   C7   C 0 1 Y N N 11.963 18.934 45.682 -0.545 1.148  -4.398 C7   PFH 2  
PFH C6   C6   C 0 1 Y N N 12.508 17.945 44.774 -1.541 0.485  -5.166 C6   PFH 3  
PFH C9   C9   C 0 1 Y N N 13.243 18.035 47.394 -0.566 2.854  -5.964 C9   PFH 4  
PFH C21  C21  C 0 1 Y N N 11.652 23.401 42.909 0.927  -3.171 -1.823 C21  PFH 5  
PFH C18  C18  C 0 1 N N N 9.689  21.805 45.675 0.443  0.323  -0.947 C18  PFH 6  
PFH C16  C16  C 0 1 N N N 11.276 20.705 44.144 1.115  -0.278 -3.166 C16  PFH 7  
PFH C19  C19  C 0 1 N N N 10.461 20.689 46.412 -0.623 0.848  -1.909 C19  PFH 8  
PFH C26  C26  C 0 1 Y N N 12.874 23.974 40.407 2.231  -5.639 -2.133 C26  PFH 9  
PFH C14  C14  C 0 1 N N N 11.469 17.412 40.538 -2.858 -3.763 -5.583 C14  PFH 10 
PFH O13  O13  O 0 1 N N N 12.491 16.652 41.222 -3.528 -2.594 -5.115 O13  PFH 11 
PFH C2   C2   C 0 1 Y N N 12.736 16.847 42.588 -3.032 -1.392 -5.518 C2   PFH 12 
PFH C1   C1   C 0 1 Y N N 13.681 15.958 43.156 -3.489 -0.791 -6.686 C1   PFH 13 
PFH O11  O11  O 0 1 N N N 14.179 15.033 42.296 -4.442 -1.395 -7.449 O11  PFH 14 
PFH C12  C12  C 0 1 N N N 15.352 14.372 42.720 -5.802 -1.087 -7.151 C12  PFH 15 
PFH C3   C3   C 0 1 Y N N 12.171 17.815 43.397 -2.058 -0.757 -4.755 C3   PFH 16 
PFH C5   C5   C 0 1 Y N N 13.446 17.031 45.318 -1.994 1.101  -6.344 C5   PFH 17 
PFH N10  N10  N 0 1 Y N N 13.772 17.117 46.611 -1.508 2.288  -6.746 N10  PFH 18 
PFH N8   N8   N 0 1 Y N N 12.359 18.922 46.960 -0.057 2.361  -4.823 N8   PFH 19 
PFH N15  N15  N 0 1 N N S 10.992 19.848 45.313 -0.052 0.603  -3.231 N15  PFH 20 
PFH C17  C17  C 0 1 N N R 10.344 21.962 44.271 1.098  -0.803 -1.730 C17  PFH 21 
PFH O20  O20  O 0 1 N N N 11.104 23.195 44.164 0.293  -1.976 -1.670 O20  PFH 22 
PFH C22  C22  C 0 1 Y N N 12.478 24.529 42.751 1.929  -3.545 -0.932 C22  PFH 23 
PFH C23  C23  C 0 1 Y N N 13.071 24.806 41.544 2.577  -4.771 -1.085 C23  PFH 24 
PFH C27  C27  C 0 1 Y N N 13.456 24.252 39.157 2.873  -6.877 -2.303 C27  PFH 25 
PFH C25  C25  C 0 1 Y N N 12.041 22.821 40.549 1.212  -5.258 -3.039 C25  PFH 26 
PFH C24  C24  C 0 1 Y N N 11.445 22.570 41.803 0.570  -4.021 -2.870 C24  PFH 27 
PFH C30  C30  C 0 1 Y N N 11.803 21.957 39.460 0.866  -6.126 -4.088 C30  PFH 28 
PFH C29  C29  C 0 1 Y N N 12.365 22.244 38.266 1.514  -7.352 -4.241 C29  PFH 29 
PFH C28  C28  C 0 1 Y N N 13.192 23.385 38.124 2.516  -7.726 -3.350 C28  PFH 30 
PFH H4   H4   H 0 1 N N N 14.752 15.362 44.916 -3.340 0.898  -8.006 H4   PFH 31 
PFH H9   H9   H 0 1 N N N 13.542 18.066 48.431 -0.177 3.809  -6.295 H9   PFH 32 
PFH H181 1H18 H 0 0 N N N 9.756  22.749 46.235 1.175  1.113  -0.741 H181 PFH 33 
PFH H182 2H18 H 0 0 N N N 8.623  21.548 45.583 -0.002 -0.004 -0.002 H182 PFH 34 
PFH H161 1H16 H 0 0 N N N 11.065 20.163 43.210 2.019  0.311  -3.355 H161 PFH 35 
PFH H162 2H16 H 0 0 N N N 12.335 21.000 44.118 1.041  -1.087 -3.900 H162 PFH 36 
PFH H191 1H19 H 0 0 N N N 9.800  20.113 47.076 -1.560 0.290  -1.800 H191 PFH 37 
PFH H192 2H19 H 0 0 N N N 11.253 21.081 47.067 -0.820 1.911  -1.736 H192 PFH 38 
PFH H141 1H14 H 0 0 N N N 10.633 17.605 41.226 -2.228 -3.505 -6.438 H141 PFH 39 
PFH H142 2H14 H 0 0 N N N 11.891 18.369 40.196 -3.596 -4.514 -5.875 H142 PFH 40 
PFH H143 3H14 H 0 0 N N N 11.106 16.840 39.671 -2.234 -4.161 -4.780 H143 PFH 41 
PFH H121 1H12 H 0 0 N N N 16.010 14.200 41.855 -6.050 -1.455 -6.152 H121 PFH 42 
PFH H122 2H12 H 0 0 N N N 15.876 14.994 43.461 -6.454 -1.553 -7.894 H122 PFH 43 
PFH H123 3H12 H 0 0 N N N 15.085 13.407 43.175 -5.936 -0.003 -7.181 H123 PFH 44 
PFH H3   H3   H 0 1 N N N 11.449 18.496 42.970 -1.712 -1.241 -3.845 H3   PFH 45 
PFH H17  H17  H 0 1 N N N 9.595  22.018 43.467 2.096  -1.058 -1.363 H17  PFH 46 
PFH H22  H22  H 0 1 N N N 12.648 25.186 43.591 2.210  -2.888 -0.114 H22  PFH 47 
PFH H23  H23  H 0 1 N N N 13.703 25.677 41.456 3.358  -5.043 -0.377 H23  PFH 48 
PFH H27  H27  H 0 1 N N N 14.088 25.116 39.014 3.658  -7.190 -1.618 H27  PFH 49 
PFH H24  H24  H 0 1 N N N 10.807 21.706 41.913 -0.216 -3.713 -3.558 H24  PFH 50 
PFH H30  H30  H 0 1 N N N 11.182 21.081 39.579 0.086  -5.854 -4.796 H30  PFH 51 
PFH H29  H29  H 0 1 N N N 12.183 21.602 37.417 1.237  -8.014 -5.056 H29  PFH 52 
PFH H28  H28  H 0 1 N N N 13.636 23.583 37.159 3.020  -8.681 -3.469 H28  PFH 53 
# 
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 
PFH C4  C1   SING Y N 1  
PFH C4  C5   DOUB Y N 2  
PFH C4  H4   SING N N 3  
PFH C7  C6   SING Y N 4  
PFH C7  N15  SING N N 5  
PFH C7  N8   DOUB Y N 6  
PFH C6  C3   DOUB Y N 7  
PFH C6  C5   SING Y N 8  
PFH C9  N10  DOUB Y N 9  
PFH C9  N8   SING Y N 10 
PFH C9  H9   SING N N 11 
PFH C21 C24  DOUB Y N 12 
PFH C21 C22  SING Y N 13 
PFH C21 O20  SING N N 14 
PFH C18 C17  SING N N 15 
PFH C18 C19  SING N N 16 
PFH C18 H181 SING N N 17 
PFH C18 H182 SING N N 18 
PFH C16 C17  SING N N 19 
PFH C16 N15  SING N N 20 
PFH C16 H161 SING N N 21 
PFH C16 H162 SING N N 22 
PFH C19 N15  SING N N 23 
PFH C19 H191 SING N N 24 
PFH C19 H192 SING N N 25 
PFH C26 C27  DOUB Y N 26 
PFH C26 C25  SING Y N 27 
PFH C26 C23  SING Y N 28 
PFH C14 O13  SING N N 29 
PFH C14 H141 SING N N 30 
PFH C14 H142 SING N N 31 
PFH C14 H143 SING N N 32 
PFH O13 C2   SING N N 33 
PFH C2  C1   DOUB Y N 34 
PFH C2  C3   SING Y N 35 
PFH C1  O11  SING N N 36 
PFH O11 C12  SING N N 37 
PFH C12 H121 SING N N 38 
PFH C12 H122 SING N N 39 
PFH C12 H123 SING N N 40 
PFH C3  H3   SING N N 41 
PFH C5  N10  SING Y N 42 
PFH C17 O20  SING N N 43 
PFH C17 H17  SING N N 44 
PFH C22 C23  DOUB Y N 45 
PFH C22 H22  SING N N 46 
PFH C23 H23  SING N N 47 
PFH C27 C28  SING Y N 48 
PFH C27 H27  SING N N 49 
PFH C25 C30  DOUB Y N 50 
PFH C25 C24  SING Y N 51 
PFH C24 H24  SING N N 52 
PFH C30 C29  SING Y N 53 
PFH C30 H30  SING N N 54 
PFH C29 C28  DOUB Y N 55 
PFH C29 H29  SING N N 56 
PFH C28 H28  SING N N 57 
# 
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 
PFH SMILES           ACDLabs              10.04 n1cnc(c2cc(OC)c(OC)cc12)N5CCC(Oc4cc3ccccc3cc4)C5                                                                                                                 
PFH InChI            InChI                1.02b InChI=1/C24H23N3O3/c1-28-22-12-20-21(13-23(22)29-2)25-15-26-24(20)27-10-9-19(14-27)30-18-8-7-16-5-3-4-6-17(16)11-18/h3-8,11-13,15,19H,9-10,14H2,1-2H3/t19-/m1/s1 
PFH InChIKey         InChI                1.02b UPTQSRGSSJRBKJ-LJQANCHMBB                                                                                                                                        
PFH SMILES_CANONICAL CACTVS               3.341 COc1cc2ncnc(N3CC[C@H](C3)Oc4ccc5ccccc5c4)c2cc1OC                                                                                                                 
PFH SMILES           CACTVS               3.341 COc1cc2ncnc(N3CC[CH](C3)Oc4ccc5ccccc5c4)c2cc1OC                                                                                                                  
PFH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 COc1cc2c(cc1OC)ncnc2[N@]3CC[C@H](C3)Oc4ccc5ccccc5c4                                                                                                              
PFH SMILES           "OpenEye OEToolkits" 1.5.0 COc1cc2c(cc1OC)ncnc2N3CCC(C3)Oc4ccc5ccccc5c4                                                                                                                     
# 
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 
PFH "SYSTEMATIC NAME" ACDLabs              10.04 6,7-dimethoxy-4-[(3R)-3-(naphthalen-2-yloxy)pyrrolidin-1-yl]quinazoline  
PFH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 6,7-dimethoxy-4-[(1S,3R)-3-naphthalen-2-yloxypyrrolidin-1-yl]quinazoline 
# 
