data_TL2
# 
_chem_comp.id                                    TL2 
_chem_comp.name                                  2-O-{4-[AMINO(IMINO)METHYL]PHENYL}-5-O-{3-[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-(4'-AMIDINOPHENYL)-5-O-(3''-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                     TL2 
_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        1Y5A 
_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 
TL2 N    N    N 0 1 N N N 12.082 28.626 40.754 -7.413 2.268  -0.850 N    TL2 1  
TL2 C1   C1   C 0 1 N N N 11.459 28.397 39.528 -7.051 1.016  -0.834 C1   TL2 2  
TL2 C2   C2   C 0 1 Y N N 12.266 27.635 38.460 -5.777 0.622  -0.193 C2   TL2 3  
TL2 C3   C3   C 0 1 Y N N 11.666 27.308 37.209 -4.962 1.591  0.395  C3   TL2 4  
TL2 C4   C4   C 0 1 Y N N 12.419 26.650 36.216 -3.776 1.220  0.991  C4   TL2 5  
TL2 C5   C5   C 0 1 Y N N 13.641 27.326 38.682 -5.391 -0.719 -0.169 C5   TL2 6  
TL2 C6   C6   C 0 1 Y N N 14.387 26.622 37.700 -4.201 -1.081 0.424  C6   TL2 7  
TL2 C7   C7   C 0 1 Y N N 13.778 26.326 36.442 -3.392 -0.115 1.008  C7   TL2 8  
TL2 O8   O8   O 0 1 N N N 14.432 25.634 35.391 -2.223 -0.476 1.596  O8   TL2 9  
TL2 C9   C9   C 0 1 N N S 15.469 24.641 35.764 -1.278 -0.686 0.544  C9   TL2 10 
TL2 C10  C10  C 0 1 N N N 15.014 23.539 36.735 -0.481 0.608  0.268  C10  TL2 11 
TL2 O11  O11  O 0 1 N N N 14.319 22.574 35.880 0.856  0.158  -0.040 O11  TL2 12 
TL2 C11  C11  C 0 1 N N R 15.847 23.820 34.549 -0.208 -1.710 0.975  C11  TL2 13 
TL2 C12  C12  C 0 1 N N R 14.745 22.777 34.515 1.128  -0.912 0.888  C12  TL2 14 
TL2 C13  C13  C 0 1 N N R 15.500 21.534 33.974 2.123  -1.894 0.233  C13  TL2 15 
TL2 O14  O14  O 0 1 N N N 14.863 20.342 34.576 2.590  -1.375 -1.014 O14  TL2 16 
TL2 O15  O15  O 0 1 N N N 17.107 23.125 34.690 -0.074 -2.730 -0.057 O15  TL2 17 
TL2 C16  C16  C 0 1 Y N N 13.206 19.974 32.726 4.951  -1.610 -0.829 C16  TL2 18 
TL2 C17  C17  C 0 1 N N N 16.897 21.699 34.620 1.296  -3.180 0.011  C17  TL2 19 
TL2 C18  C18  C 0 1 Y N N 13.724 19.699 34.044 3.809  -0.822 -0.776 C18  TL2 20 
TL2 C20  C20  C 0 1 Y N N 13.153 18.701 34.866 3.911  0.529  -0.488 C20  TL2 21 
TL2 C21  C21  C 0 1 N N N 11.230 17.015 35.323 5.279  2.533  0.076  C21  TL2 22 
TL2 N22  N22  N 0 1 N N N 11.967 16.281 36.247 4.212  3.277  0.126  N22  TL2 23 
TL2 N23  N23  N 0 1 N N N 9.972  16.796 35.273 6.517  3.088  0.317  N23  TL2 24 
TL2 C24  C24  C 0 1 Y N N 12.054 19.271 32.302 6.192  -1.052 -0.588 C24  TL2 25 
TL2 C25  C25  C 0 1 Y N N 11.425 18.322 33.121 6.304  0.292  -0.294 C25  TL2 26 
TL2 C26  C26  C 0 1 Y N N 11.938 18.031 34.435 5.162  1.091  -0.240 C26  TL2 27 
TL2 N27  N27  N 0 1 N N N 10.289 28.841 39.356 -7.855 0.059  -1.414 N27  TL2 28 
TL2 HN   HN   H 0 1 N N N 12.455 28.315 39.857 -8.248 2.526  -1.270 HN   TL2 29 
TL2 H3   H3   H 0 1 N N N 10.613 27.566 37.008 -5.259 2.629  0.382  H3   TL2 30 
TL2 H4   H4   H 0 1 N N N 11.942 26.387 35.257 -3.144 1.969  1.446  H4   TL2 31 
TL2 H5   H5   H 0 1 N N N 14.131 27.634 39.621 -6.020 -1.470 -0.623 H5   TL2 32 
TL2 H6   H6   H 0 1 N N N 15.424 26.310 37.911 -3.900 -2.118 0.439  H6   TL2 33 
TL2 H9   H9   H 0 1 N N N 16.268 25.273 36.217 -1.785 -1.021 -0.361 H9   TL2 34 
TL2 H101 1H10 H 0 0 N N N 14.408 23.908 37.595 -0.906 1.142  -0.581 H101 TL2 35 
TL2 H102 2H10 H 0 0 N N N 15.836 23.100 37.346 -0.472 1.244  1.153  H102 TL2 36 
TL2 H11  H11  H 0 1 N N N 15.954 24.464 33.645 -0.395 -2.134 1.962  H11  TL2 37 
TL2 H12  H12  H 0 1 N N N 13.844 23.027 33.907 1.470  -0.551 1.858  H12  TL2 38 
TL2 H13  H13  H 0 1 N N N 15.514 21.437 32.863 2.961  -2.091 0.902  H13  TL2 39 
TL2 H16  H16  H 0 1 N N N 13.682 20.708 32.055 4.869  -2.662 -1.058 H16  TL2 40 
TL2 H171 1H17 H 0 0 N N N 17.709 21.148 34.090 1.585  -3.659 -0.925 H171 TL2 41 
TL2 H172 2H17 H 0 0 N N N 17.007 21.177 35.599 1.429  -3.866 0.847  H172 TL2 42 
TL2 H20  H20  H 0 1 N N N 13.644 18.451 35.822 3.024  1.143  -0.448 H20  TL2 43 
TL2 H22  H22  H 0 1 N N N 11.771 15.544 35.570 4.288  4.222  0.333  H22  TL2 44 
TL2 H231 1H23 H 0 0 N N N 9.569  16.919 36.202 7.312  2.534  0.279  H231 TL2 45 
TL2 H232 2H23 H 0 0 N N N 9.432  17.334 34.596 6.594  4.032  0.523  H232 TL2 46 
TL2 H24  H24  H 0 1 N N N 11.633 19.469 31.302 7.077  -1.669 -0.629 H24  TL2 47 
TL2 H25  H25  H 0 1 N N N 10.530 17.807 32.733 7.276  0.725  -0.105 H25  TL2 48 
TL2 H271 1H27 H 0 0 N N N 10.282 29.842 39.550 -7.586 -0.873 -1.401 H271 TL2 49 
TL2 H272 2H27 H 0 0 N N N 9.833  28.674 38.459 -8.692 0.316  -1.830 H272 TL2 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 
TL2 N   C1   DOUB N E 1  
TL2 N   HN   SING N N 2  
TL2 C1  C2   SING N N 3  
TL2 C1  N27  SING N N 4  
TL2 C2  C3   DOUB Y N 5  
TL2 C2  C5   SING Y N 6  
TL2 C3  C4   SING Y N 7  
TL2 C3  H3   SING N N 8  
TL2 C4  C7   DOUB Y N 9  
TL2 C4  H4   SING N N 10 
TL2 C5  C6   DOUB Y N 11 
TL2 C5  H5   SING N N 12 
TL2 C6  C7   SING Y N 13 
TL2 C6  H6   SING N N 14 
TL2 C7  O8   SING N N 15 
TL2 O8  C9   SING N N 16 
TL2 C9  C10  SING N N 17 
TL2 C9  C11  SING N N 18 
TL2 C9  H9   SING N N 19 
TL2 C10 O11  SING N N 20 
TL2 C10 H101 SING N N 21 
TL2 C10 H102 SING N N 22 
TL2 O11 C12  SING N N 23 
TL2 C11 C12  SING N N 24 
TL2 C11 O15  SING N N 25 
TL2 C11 H11  SING N N 26 
TL2 C12 C13  SING N N 27 
TL2 C12 H12  SING N N 28 
TL2 C13 O14  SING N N 29 
TL2 C13 C17  SING N N 30 
TL2 C13 H13  SING N N 31 
TL2 O14 C18  SING N N 32 
TL2 O15 C17  SING N N 33 
TL2 C16 C18  DOUB Y N 34 
TL2 C16 C24  SING Y N 35 
TL2 C16 H16  SING N N 36 
TL2 C17 H171 SING N N 37 
TL2 C17 H172 SING N N 38 
TL2 C18 C20  SING Y N 39 
TL2 C20 C26  DOUB Y N 40 
TL2 C20 H20  SING N N 41 
TL2 C21 N22  DOUB N N 42 
TL2 C21 N23  SING N N 43 
TL2 C21 C26  SING N N 44 
TL2 N22 H22  SING N N 45 
TL2 N23 H231 SING N N 46 
TL2 N23 H232 SING N N 47 
TL2 C24 C25  DOUB Y N 48 
TL2 C24 H24  SING N N 49 
TL2 C25 C26  SING Y N 50 
TL2 C25 H25  SING N N 51 
TL2 N27 H271 SING N N 52 
TL2 N27 H272 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 
TL2 SMILES           ACDLabs              10.04 O(c1ccc(C(=[N@H])N)cc1)C3C4OCC(Oc2cc(C(=[N@H])N)ccc2)C4OC3                                                                                                                                                 
TL2 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+/m0/s1/f/h21,23H,22,24H2/b21-19+,23-20? 
TL2 InChIKey         InChI                1.02b DKBAWRNTUZFJKV-PFLJLDPUDI                                                                                                                                                                                  
TL2 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                                                                                                                                         
TL2 SMILES           CACTVS               3.341 NC(=N)c1ccc(O[CH]2CO[CH]3[CH](CO[CH]23)Oc4cccc(c4)C(N)=N)cc1                                                                                                                                               
TL2 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(\c1ccc(cc1)O[C@H]2CO[C@H]3[C@@H]2OC[C@H]3Oc4cccc(c4)C(=N)N)/N                                                                                                                                      
TL2 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(c1ccc(cc1)OC2COC3C2OCC3Oc4cccc(c4)C(=N)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 
TL2 "SYSTEMATIC NAME" ACDLabs              10.04 1,4:3,6-dianhydro-5-O-(3-carbamimidoylphenyl)-2-O-(4-carbamimidoylphenyl)-D-glucitol                                   
TL2 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 4-[[(3S,3aR,6R,6aR)-6-(3-carbamimidoylphenoxy)-2,3,3a,5,6,6a-hexahydrofuro[4,5-b]furan-3-yl]oxy]benzenecarboximidamide 
# 
