data_DF2
# 
_chem_comp.id                                    DF2 
_chem_comp.name                                  (2R)-3-{[(4Z)-5,6-DIPHENYL-6,7-DIHYDRO-4H-PYRROLO[2,3-D]PYRIMIDIN-4-YLIDENE]AMINO}PROPANE-1,2-DIOL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H20 N4 O2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-05-09 
_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                        360.409 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DF2 
_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        2BRO 
_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 
DF2 C2   C2   C 0 1 Y N N 6.008  -2.244 19.494 3.504  3.230  -2.020 C2   DF2 1  
DF2 C10  C10  C 0 1 Y N N 2.017  -4.258 19.564 5.579  -0.576 -1.159 C10  DF2 2  
DF2 C11  C11  C 0 1 Y N N 0.675  -4.577 19.762 6.531  -1.664 -1.137 C11  DF2 3  
DF2 C12  C12  C 0 1 Y N N 0.031  -5.633 19.118 6.409  -2.711 -2.049 C12  DF2 4  
DF2 C13  C13  C 0 1 Y N N -1.325 -5.903 19.363 7.328  -3.761 -2.028 C13  DF2 5  
DF2 C14  C14  C 0 1 Y N N -2.048 -5.090 20.250 8.366  -3.761 -1.096 C14  DF2 6  
DF2 C15  C15  C 0 1 Y N N -1.414 -4.025 20.872 8.485  -2.711 -0.185 C15  DF2 7  
DF2 C16  C16  C 0 1 Y N N -0.061 -3.770 20.631 7.566  -1.662 -0.205 C16  DF2 8  
DF2 C19  C19  C 0 1 Y N N 2.413  -6.585 17.124 2.999  -2.395 -0.083 C19  DF2 9  
DF2 C20  C20  C 0 1 Y N N 2.389  -7.945 16.775 2.476  -3.348 0.791  C20  DF2 10 
DF2 C21  C21  C 0 1 Y N N 2.826  -8.949 17.661 2.795  -3.300 2.148  C21  DF2 11 
DF2 C22  C22  C 0 1 Y N N 3.339  -8.759 18.919 3.638  -2.298 2.631  C22  DF2 12 
DF2 N1   N1   N 0 1 Y N N 4.764  -2.110 19.920 4.644  2.606  -2.382 N1   DF2 13 
DF2 C26  C26  C 0 1 N N N 8.648  -5.460 15.685 0.402  0.787  2.957  C26  DF2 14 
DF2 C6   C6   C 0 1 Y N N 3.848  -3.058 19.686 4.755  1.413  -1.773 C6   DF2 15 
DF2 C5   C5   C 0 1 Y N N 4.191  -4.227 19.005 3.850  0.848  -0.883 C5   DF2 16 
DF2 O27  O27  O 0 1 N N N 7.840  -6.548 15.226 -0.481 0.088  3.830  O27  DF2 17 
DF2 N9   N9   N 0 1 N N N 6.029  -5.385 17.991 1.732  1.113  0.297  N9   DF2 18 
DF2 C4   C4   C 0 1 Y N N 5.528  -4.336 18.605 2.695  1.588  -0.578 C4   DF2 19 
DF2 N3   N3   N 0 1 Y N N 6.400  -3.352 18.869 2.540  2.806  -1.173 N3   DF2 20 
DF2 N90  N90  N 0 1 Y N N 2.540  -3.106 19.975 5.797  0.537  -1.930 N90  DF2 21 
DF2 C17  C17  C 0 1 Y N N 3.350  -7.380 19.167 4.161  -1.345 1.757  C17  DF2 22 
DF2 C1   C1   C 0 1 Y N N 3.019  -4.996 18.938 4.379  -0.411 -0.499 C1   DF2 23 
DF2 C18  C18  C 0 1 Y N N 2.905  -6.305 18.383 3.841  -1.394 0.401  C18  DF2 24 
DF2 C23  C23  C 0 1 N N R 7.750  -4.582 16.538 -0.321 1.066  1.643  C23  DF2 25 
DF2 C8   C8   C 0 1 N N N 7.467  -5.401 17.808 0.531  1.841  0.638  C8   DF2 26 
DF2 O24  O24  O 0 1 N N N 8.335  -3.264 16.836 -0.723 -0.180 1.073  O24  DF2 27 
DF2 H2   H2   H 0 1 N N N 6.731  -1.427 19.659 3.338  4.203  -2.470 H2   DF2 28 
DF2 H12  H12  H 0 1 N N N 0.593  -6.263 18.408 5.605  -2.725 -2.781 H12  DF2 29 
DF2 H13  H13  H 0 1 N N N -1.820 -6.751 18.860 7.234  -4.578 -2.737 H13  DF2 30 
DF2 H14  H14  H 0 1 N N N -3.113 -5.297 20.451 9.081  -4.578 -1.079 H14  DF2 31 
DF2 H15  H15  H 0 1 N N N -1.980 -3.376 21.561 9.293  -2.711 0.541  H15  DF2 32 
DF2 H16  H16  H 0 1 N N N 0.431  -2.921 21.134 7.673  -0.851 0.511  H16  DF2 33 
DF2 H19  H19  H 0 1 N N N 2.063  -5.795 16.439 2.740  -2.445 -1.138 H19  DF2 34 
DF2 H20  H20  H 0 1 N N N 2.017  -8.236 15.778 1.819  -4.126 0.415  H20  DF2 35 
DF2 H21  H21  H 0 1 N N N 2.748  -9.991 17.308 2.389  -4.042 2.828  H21  DF2 36 
DF2 H22  H22  H 0 1 N N N 3.681  -9.548 19.610 3.887  -2.261 3.687  H22  DF2 37 
DF2 H261 1H26 H 0 0 N N N 9.573  -5.790 16.214 0.698  1.718  3.449  H261 DF2 38 
DF2 H262 2H26 H 0 0 N N N 9.151  -4.905 14.859 1.283  0.155  2.804  H262 DF2 39 
DF2 H27  H27  H 0 1 N N N 8.402  -7.097 14.692 -0.181 0.273  4.733  H27  DF2 40 
DF2 H90  H90  H 0 1 N N N 2.020  -2.364 20.444 6.601  0.694  -2.523 H90  DF2 41 
DF2 H17  H17  H 0 1 N N N 3.780  -7.092 20.141 4.817  -0.572 2.149  H17  DF2 42 
DF2 H23  H23  H 0 1 N N N 6.788  -4.427 15.995 -1.240 1.627  1.848  H23  DF2 43 
DF2 H8C1 1H8C H 0 0 N N N 7.898  -6.429 17.777 -0.039 2.011  -0.282 H8C1 DF2 44 
DF2 H8C2 2H8C H 0 0 N N N 8.031  -5.043 18.701 0.807  2.818  1.048  H8C2 DF2 45 
DF2 H24  H24  H 0 1 N N N 8.510  -2.758 16.051 -1.490 0.011  0.512  H24  DF2 46 
DF2 HN1  HN1  H 0 1 N N N 5.791  -6.189 18.537 1.876  0.205  0.724  HN1  DF2 47 
# 
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 
DF2 C2  N1   SING Y N 1  
DF2 C2  N3   DOUB Y N 2  
DF2 C2  H2   SING N N 3  
DF2 C10 C11  SING N N 4  
DF2 C10 N90  SING Y N 5  
DF2 C10 C1   DOUB Y N 6  
DF2 C11 C12  DOUB Y N 7  
DF2 C11 C16  SING Y N 8  
DF2 C12 C13  SING Y N 9  
DF2 C12 H12  SING N N 10 
DF2 C13 C14  DOUB Y N 11 
DF2 C13 H13  SING N N 12 
DF2 C14 C15  SING Y N 13 
DF2 C14 H14  SING N N 14 
DF2 C15 C16  DOUB Y N 15 
DF2 C15 H15  SING N N 16 
DF2 C16 H16  SING N N 17 
DF2 C19 C20  DOUB Y N 18 
DF2 C19 C18  SING Y N 19 
DF2 C19 H19  SING N N 20 
DF2 C20 C21  SING Y N 21 
DF2 C20 H20  SING N N 22 
DF2 C21 C22  DOUB Y N 23 
DF2 C21 H21  SING N N 24 
DF2 C22 C17  SING Y N 25 
DF2 C22 H22  SING N N 26 
DF2 N1  C6   DOUB Y N 27 
DF2 C26 O27  SING N N 28 
DF2 C26 C23  SING N N 29 
DF2 C26 H261 SING N N 30 
DF2 C26 H262 SING N N 31 
DF2 C6  C5   SING Y N 32 
DF2 C6  N90  SING Y N 33 
DF2 C5  C4   DOUB Y N 34 
DF2 C5  C1   SING Y N 35 
DF2 O27 H27  SING N N 36 
DF2 N9  C4   SING N Z 37 
DF2 N9  C8   SING N N 38 
DF2 C4  N3   SING Y N 39 
DF2 N90 H90  SING N N 40 
DF2 C17 C18  DOUB Y N 41 
DF2 C17 H17  SING N N 42 
DF2 C1  C18  SING N N 43 
DF2 C23 C8   SING N N 44 
DF2 C23 O24  SING N N 45 
DF2 C23 H23  SING N N 46 
DF2 C8  H8C1 SING N N 47 
DF2 C8  H8C2 SING N N 48 
DF2 O24 H24  SING N N 49 
DF2 HN1 N9   SING N N 50 
# 
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 
DF2 SMILES           ACDLabs              10.04 n1c3c(c(nc1)NCC(O)CO)c(c(c2ccccc2)n3)c4ccccc4                                                                                                                            
DF2 InChI            InChI                1.02b InChI=1/C21H20N4O2/c26-12-16(27)11-22-20-18-17(14-7-3-1-4-8-14)19(15-9-5-2-6-10-15)25-21(18)24-13-23-20/h1-10,13,16,26-27H,11-12H2,(H2,22,23,24,25)/t16-/m1/s1/f/h22,25H 
DF2 InChIKey         InChI                1.02b TWEONIHFGKSPLC-IOVUNQANDD                                                                                                                                                
DF2 SMILES_CANONICAL CACTVS               3.341 OC[C@H](O)CNc1ncnc2[nH]c(c3ccccc3)c(c4ccccc4)c12                                                                                                                         
DF2 SMILES           CACTVS               3.341 OC[CH](O)CNc1ncnc2[nH]c(c3ccccc3)c(c4ccccc4)c12                                                                                                                          
DF2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)c2c3c([nH]c2c4ccccc4)ncnc3NC[C@H](CO)O                                                                                                                         
DF2 SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc(cc1)c2c3c([nH]c2c4ccccc4)ncnc3NCC(CO)O                                                                                                                             
# 
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 
DF2 "SYSTEMATIC NAME" ACDLabs              10.04 (2R)-3-[(5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]propane-1,2-diol 
DF2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (2R)-3-[(5,6-diphenyl-7H-pyrrolo[3,2-e]pyrimidin-4-yl)amino]propane-1,2-diol 
# 
