data_TL4
# 
_chem_comp.id                                    TL4 
_chem_comp.name                                  2-O-{3-[AMINO(IMINO)METHYL]PHENYL}-5-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-O-(3'-AMIDINOPHENYL)-5-O-(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                     TL4 
_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        1Y5U 
_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 
TL4 C4   C4   C 0 1 Y N N 37.885 24.389 55.993 -6.309 0.218  0.405  C4   TL4 1  
TL4 C5   C5   C 0 1 Y N N 39.317 24.482 56.228 -5.561 -0.668 1.183  C5   TL4 2  
TL4 C6   C6   C 0 1 Y N N 40.232 25.016 55.230 -4.185 -0.595 1.177  C6   TL4 3  
TL4 C7   C7   C 0 1 Y N N 39.751 25.533 53.940 -3.542 0.359  0.398  C7   TL4 4  
TL4 O8   O8   O 0 1 N N N 40.855 26.015 53.051 -2.186 0.428  0.395  O8   TL4 5  
TL4 C9   C9   C 0 1 N N R 42.320 26.338 53.533 -1.746 -0.153 -0.835 C9   TL4 6  
TL4 C10  C10  C 0 1 N N N 42.865 27.204 52.326 -1.499 -1.667 -0.659 C10  TL4 7  
TL4 O11  O11  O 0 1 N N N 43.249 26.177 51.388 -0.091 -1.780 -0.362 O11  TL4 8  
TL4 C12  C12  C 0 1 N N R 43.964 25.288 52.268 0.565  -0.834 -1.232 C12  TL4 9  
TL4 C13  C13  C 0 1 N N S 44.142 23.871 51.591 1.860  -0.349 -0.548 C13  TL4 10 
TL4 O14  O14  O 0 1 N N N 45.231 23.040 52.245 2.972  -0.473 -1.437 O14  TL4 11 
TL4 C15  C15  C 0 1 Y N N 45.166 21.666 51.804 4.072  -0.674 -0.665 C15  TL4 12 
TL4 C16  C16  C 0 1 Y N N 44.735 21.259 50.456 4.314  -1.926 -0.115 C16  TL4 13 
TL4 C17  C17  C 0 1 Y N N 44.700 19.840 50.116 5.431  -2.135 0.672  C17  TL4 14 
TL4 C18  C18  C 0 1 Y N N 45.059 18.843 51.094 6.313  -1.102 0.915  C18  TL4 15 
TL4 C19  C19  C 0 1 Y N N 45.467 19.220 52.447 6.078  0.159  0.366  C19  TL4 16 
TL4 C20  C20  C 0 1 N N N 45.841 18.189 53.490 7.022  1.270  0.626  C20  TL4 17 
TL4 N21  N21  N 0 1 N N N 46.695 18.521 54.433 6.800  2.446  0.113  N21  TL4 18 
TL4 N22  N22  N 0 1 N N N 45.279 16.940 53.437 8.134  1.060  1.411  N22  TL4 19 
TL4 C23  C23  C 0 1 Y N N 45.526 20.648 52.802 4.954  0.368  -0.431 C23  TL4 20 
TL4 C24  C24  C 0 1 N N N 42.628 23.476 51.767 1.585  1.137  -0.226 C24  TL4 21 
TL4 O25  O25  O 0 1 N N N 42.378 23.806 53.154 0.148  1.237  -0.147 O25  TL4 22 
TL4 C26  C26  C 0 1 N N R 43.072 25.002 53.474 -0.368 0.414  -1.238 C26  TL4 23 
TL4 C27  C27  C 0 1 Y N N 38.253 25.469 53.804 -4.283 1.241  -0.378 C27  TL4 24 
TL4 C28  C28  C 0 1 Y N N 37.346 24.894 54.742 -5.659 1.170  -0.381 C28  TL4 25 
TL4 N1   N1   N 0 1 N N N 35.772 23.283 56.657 -8.391 -0.751 1.140  N1   TL4 26 
TL4 C2   C2   C 0 1 N N N 36.855 23.902 57.053 -7.786 0.142  0.409  C2   TL4 27 
TL4 N3   N3   N 0 1 N N N 37.015 24.100 58.411 -8.523 1.017  -0.360 N3   TL4 28 
TL4 H5   H5   H 0 1 N N N 39.722 24.137 57.194 -6.061 -1.409 1.789  H5   TL4 29 
TL4 H6   H6   H 0 1 N N N 41.312 25.029 55.456 -3.606 -1.279 1.779  H6   TL4 30 
TL4 H9   H9   H 0 1 N N N 42.406 26.817 54.536 -2.477 0.025  -1.623 H9   TL4 31 
TL4 H101 1H10 H 0 0 N N N 43.666 27.934 52.587 -2.094 -2.055 0.168  H101 TL4 32 
TL4 H102 2H10 H 0 0 N N N 42.157 27.969 51.931 -1.737 -2.200 -1.580 H102 TL4 33 
TL4 H12  H12  H 0 1 N N N 44.942 25.760 52.520 0.741  -1.234 -2.231 H12  TL4 34 
TL4 H13  H13  H 0 1 N N N 44.525 23.766 50.549 2.041  -0.910 0.368  H13  TL4 35 
TL4 H16  H16  H 0 1 N N N 44.440 22.012 49.706 3.628  -2.738 -0.302 H16  TL4 36 
TL4 H17  H17  H 0 1 N N N 44.398 19.517 49.106 5.615  -3.111 1.097  H17  TL4 37 
TL4 H18  H18  H 0 1 N N N 45.021 17.780 50.804 7.185  -1.269 1.531  H18  TL4 38 
TL4 H21  H21  H 0 1 N N N 47.249 18.076 53.702 7.418  3.174  0.283  H21  TL4 39 
TL4 H221 1H22 H 0 0 N N N 45.451 16.545 52.513 8.300  0.184  1.793  H221 TL4 40 
TL4 H222 2H22 H 0 0 N N N 45.531 16.245 54.140 8.752  1.787  1.581  H222 TL4 41 
TL4 H23  H23  H 0 1 N N N 45.839 20.955 53.814 4.767  1.342  -0.859 H23  TL4 42 
TL4 H241 1H24 H 0 0 N N N 42.381 22.427 51.483 2.038  1.408  0.728  H241 TL4 43 
TL4 H242 2H24 H 0 0 N N N 41.931 23.953 51.039 1.967  1.774  -1.023 H242 TL4 44 
TL4 H26  H26  H 0 1 N N N 43.482 24.779 54.487 -0.383 0.942  -2.191 H26  TL4 45 
TL4 H27  H27  H 0 1 N N N 37.762 25.893 52.912 -3.779 1.981  -0.983 H27  TL4 46 
TL4 H28  H28  H 0 1 N N N 36.269 24.842 54.509 -6.234 1.857  -0.984 H28  TL4 47 
TL4 HN1  HN1  H 0 1 N N N 34.932 23.773 56.966 -9.360 -0.801 1.142  HN1  TL4 48 
TL4 HN31 1HN3 H 0 0 N N N 37.153 25.100 58.558 -8.072 1.683  -0.903 HN31 TL4 49 
TL4 HN32 2HN3 H 0 0 N N N 36.340 23.781 59.106 -9.491 0.965  -0.360 HN32 TL4 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 
TL4 C4  C5   DOUB Y N 1  
TL4 C4  C28  SING Y N 2  
TL4 C4  C2   SING N N 3  
TL4 C5  C6   SING Y N 4  
TL4 C5  H5   SING N N 5  
TL4 C6  C7   DOUB Y N 6  
TL4 C6  H6   SING N N 7  
TL4 C7  O8   SING N N 8  
TL4 C7  C27  SING Y N 9  
TL4 O8  C9   SING N N 10 
TL4 C9  C10  SING N N 11 
TL4 C9  C26  SING N N 12 
TL4 C9  H9   SING N N 13 
TL4 C10 O11  SING N N 14 
TL4 C10 H101 SING N N 15 
TL4 C10 H102 SING N N 16 
TL4 O11 C12  SING N N 17 
TL4 C12 C13  SING N N 18 
TL4 C12 C26  SING N N 19 
TL4 C12 H12  SING N N 20 
TL4 C13 O14  SING N N 21 
TL4 C13 C24  SING N N 22 
TL4 C13 H13  SING N N 23 
TL4 O14 C15  SING N N 24 
TL4 C15 C16  DOUB Y N 25 
TL4 C15 C23  SING Y N 26 
TL4 C16 C17  SING Y N 27 
TL4 C16 H16  SING N N 28 
TL4 C17 C18  DOUB Y N 29 
TL4 C17 H17  SING N N 30 
TL4 C18 C19  SING Y N 31 
TL4 C18 H18  SING N N 32 
TL4 C19 C20  SING N N 33 
TL4 C19 C23  DOUB Y N 34 
TL4 C20 N21  DOUB N N 35 
TL4 C20 N22  SING N N 36 
TL4 N21 H21  SING N N 37 
TL4 N22 H221 SING N N 38 
TL4 N22 H222 SING N N 39 
TL4 C23 H23  SING N N 40 
TL4 C24 O25  SING N N 41 
TL4 C24 H241 SING N N 42 
TL4 C24 H242 SING N N 43 
TL4 O25 C26  SING N N 44 
TL4 C26 H26  SING N N 45 
TL4 C27 C28  DOUB Y N 46 
TL4 C27 H27  SING N N 47 
TL4 C28 H28  SING N N 48 
TL4 N1  C2   DOUB N N 49 
TL4 N1  HN1  SING N N 50 
TL4 C2  N3   SING N N 51 
TL4 N3  HN31 SING N N 52 
TL4 N3  HN32 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 
TL4 SMILES           ACDLabs              10.04 O(c1ccc(C(=[N@H])N)cc1)C3C4OCC(Oc2cc(C(=[N@H])N)ccc2)C4OC3                                                                                                                                                 
TL4 InChI            InChI                1.02b InChI=1/C20H22N4O4/c21-19(22)11-4-6-13(7-5-11)27-15-9-25-18-16(10-26-17(15)18)28-14-3-1-2-12(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? 
TL4 InChIKey         InChI                1.02b DKBAWRNTUZFJKV-VYDUPPSCDH                                                                                                                                                                                  
TL4 SMILES_CANONICAL CACTVS               3.341 NC(=N)c1ccc(O[C@@H]2CO[C@@H]3[C@H](CO[C@H]23)Oc4cccc(c4)C(N)=N)cc1                                                                                                                                         
TL4 SMILES           CACTVS               3.341 NC(=N)c1ccc(O[CH]2CO[CH]3[CH](CO[CH]23)Oc4cccc(c4)C(N)=N)cc1                                                                                                                                               
TL4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)O[C@H]2CO[C@H]3[C@@H]2OC[C@H]3Oc4ccc(cc4)C(=N)N)C(=N)N                                                                                                                                          
TL4 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)OC2COC3C2OCC3Oc4ccc(cc4)C(=N)N)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 
TL4 "SYSTEMATIC NAME" ACDLabs              10.04 1,4:3,6-dianhydro-2-O-(3-carbamimidoylphenyl)-5-O-(4-carbamimidoylphenyl)-D-glucitol                                   
TL4 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[[(3R,3aR,6S,6aR)-6-(3-carbamimidoylphenoxy)-2,3,3a,5,6,6a-hexahydrofuro[4,5-b]furan-3-yl]oxy]benzenecarboximidamide 
# 
