data_TL3
# 
_chem_comp.id                                    TL3 
_chem_comp.name                                  2,5-BIS-O-{4-[AMINO(IMINO)METHYL]PHENYL}-1,4:3,6-DIANHYDRO-D-GLUCITOL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H22 N4 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "2,5-O,O-BIS-{4',4''-AMIDINOPHENYL}-1,4:3,6-DIANHYDRO-D-SORBITOL" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2004-12-08 
_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                        382.413 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     TL3 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1Y5B 
_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 
TL3 N1   N1   N 0 1 N N N 12.062 31.487 25.146 8.326  1.826  0.163  N1   TL3 1  
TL3 C1   C1   C 0 1 N N N 12.228 30.188 25.242 7.840  0.621  0.264  C1   TL3 2  
TL3 N2   N2   N 0 1 N N N 12.211 29.584 26.479 8.689  -0.465 0.281  N2   TL3 3  
TL3 C2   C2   C 0 1 Y N N 12.269 29.257 24.077 6.378  0.418  0.360  C2   TL3 4  
TL3 C3   C3   C 0 1 Y N N 13.139 28.085 24.108 5.517  1.517  0.342  C3   TL3 5  
TL3 C4   C4   C 0 1 Y N N 13.132 27.219 22.960 4.156  1.324  0.432  C4   TL3 6  
TL3 C5   C5   C 0 1 Y N N 12.281 27.549 21.812 3.640  0.039  0.539  C5   TL3 7  
TL3 O1   O1   O 0 1 N N N 12.187 26.807 20.650 2.298  -0.147 0.627  O1   TL3 8  
TL3 C6   C6   C 0 1 N N R 12.883 25.518 20.569 1.861  -0.613 -0.652 C6   TL3 9  
TL3 C7   C7   C 0 1 N N N 12.812 25.197 19.052 1.466  0.577  -1.554 C7   TL3 10 
TL3 O2   O2   O 0 1 N N N 11.659 24.337 18.867 0.042  0.722  -1.370 O2   TL3 11 
TL3 C8   C8   C 0 1 N N R 11.360 23.665 20.152 -0.483 -0.621 -1.334 C8   TL3 12 
TL3 C9   C9   C 0 1 N N S 9.861  23.973 20.450 -1.757 -0.631 -0.462 C9   TL3 13 
TL3 O3   O3   O 0 1 N N N 9.309  22.751 21.048 -2.835 -1.260 -1.159 O3   TL3 14 
TL3 C10  C10  C 0 1 Y N N 9.060  21.760 20.091 -3.981 -0.696 -0.700 C10  TL3 15 
TL3 C11  C11  C 0 1 Y N N 9.029  20.415 20.553 -4.363 0.562  -1.151 C11  TL3 16 
TL3 C12  C12  C 0 1 Y N N 8.747  19.383 19.615 -5.526 1.138  -0.687 C12  TL3 17 
TL3 C13  C13  C 0 1 Y N N 8.535  19.681 18.219 -6.320 0.456  0.237  C13  TL3 18 
TL3 C14  C14  C 0 1 N N N 8.257  18.596 17.247 -7.569 1.072  0.737  C14  TL3 19 
TL3 N3   N3   N 0 1 N N N 8.515  17.348 17.561 -7.928 2.252  0.316  N3   TL3 20 
TL3 N4   N4   N 0 1 N N N 7.423  18.926 16.195 -8.352 0.398  1.649  N4   TL3 21 
TL3 C15  C15  C 0 1 Y N N 8.565  21.033 17.735 -5.933 -0.807 0.687  C15  TL3 22 
TL3 C16  C16  C 0 1 Y N N 8.890  22.064 18.670 -4.772 -1.379 0.215  C16  TL3 23 
TL3 C17  C17  C 0 1 N N N 9.827  25.028 21.543 -1.359 -1.456 0.781  C17  TL3 24 
TL3 O4   O4   O 0 1 N N N 11.084 24.733 22.264 0.076  -1.332 0.862  O4   TL3 25 
TL3 C18  C18  C 0 1 N N R 12.134 24.327 21.278 0.561  -1.434 -0.512 C18  TL3 26 
TL3 C19  C19  C 0 1 Y N N 11.441 28.696 21.813 4.494  -1.057 0.556  C19  TL3 27 
TL3 C20  C20  C 0 1 Y N N 11.429 29.528 22.943 5.856  -0.872 0.462  C20  TL3 28 
TL3 HN1  HN1  H 0 1 N N N 12.871 32.103 25.221 7.729  2.590  0.151  HN1  TL3 29 
TL3 HN21 1HN2 H 0 0 N N N 11.341 29.834 26.949 9.648  -0.332 0.219  HN21 TL3 30 
TL3 HN22 2HN2 H 0 0 N N N 12.340 28.575 26.554 8.328  -1.362 0.360  HN22 TL3 31 
TL3 H3   H3   H 0 1 N N N 13.784 27.860 24.974 5.918  2.516  0.259  H3   TL3 32 
TL3 H4   H4   H 0 1 N N N 13.768 26.318 22.960 3.489  2.174  0.419  H4   TL3 33 
TL3 H6   H6   H 0 1 N N N 13.888 25.603 21.045 2.640  -1.209 -1.126 H6   TL3 34 
TL3 H71  1H7  H 0 1 N N N 13.756 24.763 18.648 1.984  1.482  -1.237 H71  TL3 35 
TL3 H72  2H7  H 0 1 N N N 12.792 26.107 18.409 1.693  0.354  -2.596 H72  TL3 36 
TL3 H8   H8   H 0 1 N N N 11.609 22.580 20.087 -0.651 -1.034 -2.329 H8   TL3 37 
TL3 H9   H9   H 0 1 N N N 9.311  24.301 19.537 -2.031 0.384  -0.175 H9   TL3 38 
TL3 H11  H11  H 0 1 N N N 9.219  20.178 21.613 -3.748 1.088  -1.866 H11  TL3 39 
TL3 H12  H12  H 0 1 N N N 8.692  18.341 19.974 -5.822 2.115  -1.038 H12  TL3 40 
TL3 HN3  HN3  H 0 1 N N N 7.775  16.689 17.317 -8.747 2.655  0.644  HN3  TL3 41 
TL3 HN41 1HN4 H 0 0 N N N 7.788  19.744 15.707 -8.084 -0.480 1.963  HN41 TL3 42 
TL3 HN42 2HN4 H 0 0 N N N 7.232  18.180 15.527 -9.170 0.801  1.977  HN42 TL3 43 
TL3 H15  H15  H 0 1 N N N 8.346  21.272 16.681 -6.545 -1.336 1.402  H15  TL3 44 
TL3 H16  H16  H 0 1 N N N 9.010  23.094 18.295 -4.472 -2.356 0.563  H16  TL3 45 
TL3 H171 1H17 H 0 0 N N N 8.906  25.036 22.171 -1.827 -1.044 1.675  H171 TL3 46 
TL3 H172 2H17 H 0 0 N N N 9.714  26.079 21.189 -1.643 -2.500 0.650  H172 TL3 47 
TL3 H18  H18  H 0 1 N N N 12.891 23.719 21.826 0.668  -2.467 -0.844 H18  TL3 48 
TL3 H19  H19  H 0 1 N N N 10.805 28.938 20.945 4.089  -2.055 0.639  H19  TL3 49 
TL3 H20  H20  H 0 1 N N N 10.755 30.401 22.940 6.519  -1.724 0.475  H20  TL3 50 
# 
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 
TL3 N1  C1   DOUB N N 1  
TL3 N1  HN1  SING N N 2  
TL3 C1  N2   SING N N 3  
TL3 C1  C2   SING N N 4  
TL3 N2  HN21 SING N N 5  
TL3 N2  HN22 SING N N 6  
TL3 C2  C3   DOUB Y N 7  
TL3 C2  C20  SING Y N 8  
TL3 C3  C4   SING Y N 9  
TL3 C3  H3   SING N N 10 
TL3 C4  C5   DOUB Y N 11 
TL3 C4  H4   SING N N 12 
TL3 C5  O1   SING N N 13 
TL3 C5  C19  SING Y N 14 
TL3 O1  C6   SING N N 15 
TL3 C6  C7   SING N N 16 
TL3 C6  C18  SING N N 17 
TL3 C6  H6   SING N N 18 
TL3 C7  O2   SING N N 19 
TL3 C7  H71  SING N N 20 
TL3 C7  H72  SING N N 21 
TL3 O2  C8   SING N N 22 
TL3 C8  C9   SING N N 23 
TL3 C8  C18  SING N N 24 
TL3 C8  H8   SING N N 25 
TL3 C9  O3   SING N N 26 
TL3 C9  C17  SING N N 27 
TL3 C9  H9   SING N N 28 
TL3 O3  C10  SING N N 29 
TL3 C10 C11  DOUB Y N 30 
TL3 C10 C16  SING Y N 31 
TL3 C11 C12  SING Y N 32 
TL3 C11 H11  SING N N 33 
TL3 C12 C13  DOUB Y N 34 
TL3 C12 H12  SING N N 35 
TL3 C13 C14  SING N N 36 
TL3 C13 C15  SING Y N 37 
TL3 C14 N3   DOUB N N 38 
TL3 C14 N4   SING N N 39 
TL3 N3  HN3  SING N N 40 
TL3 N4  HN41 SING N N 41 
TL3 N4  HN42 SING N N 42 
TL3 C15 C16  DOUB Y N 43 
TL3 C15 H15  SING N N 44 
TL3 C16 H16  SING N N 45 
TL3 C17 O4   SING N N 46 
TL3 C17 H171 SING N N 47 
TL3 C17 H172 SING N N 48 
TL3 O4  C18  SING N N 49 
TL3 C18 H18  SING N N 50 
TL3 C19 C20  DOUB Y N 51 
TL3 C19 H19  SING N N 52 
TL3 C20 H20  SING N N 53 
# 
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 
TL3 SMILES           ACDLabs              10.04 O(c1ccc(C(=[N@H])N)cc1)C3C4OCC(Oc2ccc(C(=[N@H])N)cc2)C4OC3 
TL3 InChI            InChI                1.02b 
InChI=1/C20H22N4O4/c21-19(22)11-1-5-13(6-2-11)27-15-9-25-18-16(10-26-17(15)18)28-14-7-3-12(4-8-14)20(23)24/h1-8,15-18H,9-10H2,(H3,21,22)(H3,23,24)/t15-,16+,17-,18-/m1/s1/f/h21,23H,22,24H2/b21-19-,23-20?/t15-,16+,17+,18+/m0 
TL3 InChIKey         InChI                1.02b CDEVHSIVANGYRI-XGTNTBLVDP 
TL3 SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(O[C@@H]2CO[C@@H]3[C@H](CO[C@H]23)Oc4ccc(cc4)C(N)=N)cc1 
TL3 SMILES           CACTVS               3.341 NC(=N)c1ccc(O[CH]2CO[CH]3[CH](CO[CH]23)Oc4ccc(cc4)C(N)=N)cc1 
TL3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=N)N)O[C@H]2CO[C@H]3[C@@H]2OC[C@H]3Oc4ccc(cc4)C(=N)N 
TL3 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(=N)N)OC2COC3C2OCC3Oc4ccc(cc4)C(=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 
TL3 "SYSTEMATIC NAME" ACDLabs              10.04 1,4:3,6-dianhydro-2,5-bis-O-(4-carbamimidoylphenyl)-D-glucitol                                                         
TL3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[[(3R,3aR,6S,6aR)-6-(4-carbamimidoylphenoxy)-2,3,3a,5,6,6a-hexahydrofuro[4,5-b]furan-3-yl]oxy]benzenecarboximidamide 
# 
