data_TL1
# 
_chem_comp.id                                    TL1 
_chem_comp.name                                  2,5-BIS-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                         "2,5-O,O-BIS-(3',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                     TL1 
_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        1Y59 
_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 
TL1 N1   N1   N 0 1 N N N 46.576 18.441 54.201 6.069  2.563  1.176  N1   TL1 1  
TL1 C1   C1   C 0 1 N N N 45.706 18.268 53.240 6.650  1.442  0.858  C1   TL1 2  
TL1 N2   N2   N 0 1 N N N 45.230 16.972 53.127 8.025  1.372  0.797  N2   TL1 3  
TL1 C2   C2   C 0 1 Y N N 45.175 19.324 52.356 5.834  0.242  0.561  C2   TL1 4  
TL1 C3   C3   C 0 1 Y N N 44.626 19.040 51.067 6.454  -0.960 0.220  C3   TL1 5  
TL1 C4   C4   C 0 1 Y N N 44.146 20.065 50.237 5.691  -2.075 -0.056 C4   TL1 6  
TL1 C5   C5   C 0 1 Y N N 44.186 21.432 50.622 4.311  -2.007 0.004  C5   TL1 7  
TL1 C6   C6   C 0 1 Y N N 44.709 21.729 51.914 3.685  -0.815 0.342  C6   TL1 8  
TL1 O1   O1   O 0 1 N N N 44.643 23.027 52.405 2.329  -0.752 0.399  O1   TL1 9  
TL1 C7   C7   C 0 1 N N R 43.819 24.156 51.872 1.860  -0.712 -0.950 C7   TL1 10 
TL1 C8   C8   C 0 1 N N N 44.172 25.507 52.614 1.742  0.749  -1.437 C8   TL1 11 
TL1 O2   O2   O 0 1 N N N 42.969 26.324 52.434 0.368  1.112  -1.186 O2   TL1 12 
TL1 C9   C9   C 0 1 N N R 41.832 25.457 52.283 -0.411 -0.046 -1.549 C9   TL1 13 
TL1 C10  C10  C 0 1 N N S 40.992 25.572 53.594 -1.696 -0.067 -0.693 C10  TL1 14 
TL1 O3   O3   O 0 1 N N N 39.593 25.200 53.310 -2.848 -0.228 -1.524 O3   TL1 15 
TL1 C11  C11  C 0 1 Y N N 38.691 25.089 54.342 -3.879 0.390  -0.889 C11  TL1 16 
TL1 C12  C12  C 0 1 Y N N 37.766 24.018 54.278 -3.989 1.773  -0.928 C12  TL1 17 
TL1 C13  C13  C 0 1 Y N N 36.789 23.788 55.260 -5.035 2.406  -0.284 C13  TL1 18 
TL1 C14  C14  C 0 1 Y N N 36.755 24.686 56.340 -5.978 1.666  0.402  C14  TL1 19 
TL1 C15  C15  C 0 1 Y N N 37.602 25.811 56.349 -5.875 0.276  0.445  C15  TL1 20 
TL1 C16  C16  C 0 1 N N N 37.655 26.692 57.572 -6.884 -0.521 1.180  C16  TL1 21 
TL1 N3   N3   N 0 1 N N N 38.815 27.149 57.982 -6.787 -1.819 1.220  N3   TL1 22 
TL1 N4   N4   N 0 1 N N N 36.466 26.980 58.192 -7.927 0.112  1.823  N4   TL1 23 
TL1 C17  C17  C 0 1 Y N N 38.727 25.952 55.450 -4.822 -0.362 -0.209 C17  TL1 24 
TL1 C18  C18  C 0 1 N N N 41.704 24.571 54.537 -1.517 -1.292 0.230  C18  TL1 25 
TL1 O4   O4   O 0 1 N N N 42.224 23.504 53.642 -0.089 -1.486 0.312  O4   TL1 26 
TL1 C19  C19  C 0 1 N N R 42.308 23.995 52.274 0.420  -1.261 -1.038 C19  TL1 27 
TL1 C20  C20  C 0 1 Y N N 45.254 20.690 52.745 4.443  0.309  0.627  C20  TL1 28 
TL1 HN1  HN1  H 0 1 N N N 47.032 17.921 53.452 5.101  2.612  1.219  HN1  TL1 29 
TL1 HN21 1HN2 H 0 0 N N N 44.845 16.655 54.017 8.559  2.157  0.992  HN21 TL1 30 
TL1 HN22 2HN2 H 0 0 N N N 44.552 16.837 52.378 8.458  0.536  0.564  HN22 TL1 31 
TL1 H3   H3   H 0 1 N N N 44.571 18.000 50.703 7.531  -1.017 0.172  H3   TL1 32 
TL1 H4   H4   H 0 1 N N N 43.726 19.789 49.255 6.172  -3.005 -0.321 H4   TL1 33 
TL1 H5   H5   H 0 1 N N N 43.827 22.228 49.948 3.718  -2.883 -0.213 H5   TL1 34 
TL1 H7   H7   H 0 1 N N N 44.009 24.159 50.773 2.525  -1.279 -1.601 H7   TL1 35 
TL1 H81  1H8  H 0 1 N N N 45.114 25.991 52.267 2.414  1.393  -0.871 H81  TL1 36 
TL1 H82  2H8  H 0 1 N N N 44.489 25.381 53.676 1.962  0.812  -2.503 H82  TL1 37 
TL1 H9   H9   H 0 1 N N N 41.276 25.728 51.355 -0.617 -0.096 -2.618 H9   TL1 38 
TL1 H10  H10  H 0 1 N N N 40.940 26.593 54.039 -1.776 0.847  -0.104 H10  TL1 39 
TL1 H12  H12  H 0 1 N N N 37.809 23.327 53.419 -3.254 2.357  -1.462 H12  TL1 40 
TL1 H13  H13  H 0 1 N N N 36.083 22.944 55.187 -5.116 3.483  -0.316 H13  TL1 41 
TL1 H14  H14  H 0 1 N N N 36.064 24.508 57.181 -6.794 2.164  0.905  H14  TL1 42 
TL1 HN3  HN3  H 0 1 N N N 39.573 26.546 57.663 -7.448 -2.340 1.701  HN3  TL1 43 
TL1 HN41 1HN4 H 0 0 N N N 35.985 26.111 58.422 -8.588 -0.410 2.304  HN41 TL1 44 
TL1 HN42 2HN4 H 0 0 N N N 36.502 27.576 59.019 -7.999 1.078  1.794  HN42 TL1 45 
TL1 H17  H17  H 0 1 N N N 39.554 26.667 55.599 -4.738 -1.438 -0.179 H17  TL1 46 
TL1 H181 1H18 H 0 0 N N N 41.059 24.193 55.364 -1.929 -1.086 1.218  H181 TL1 47 
TL1 H182 2H18 H 0 0 N N N 42.483 25.036 55.185 -1.995 -2.169 -0.206 H182 TL1 48 
TL1 H19  H19  H 0 1 N N N 41.736 23.306 51.610 0.335  -2.144 -1.671 H19  TL1 49 
TL1 H20  H20  H 0 1 N N N 45.743 20.946 53.700 3.957  1.237  0.891  H20  TL1 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 
TL1 N1  C1   DOUB N N 1  
TL1 N1  HN1  SING N N 2  
TL1 C1  N2   SING N N 3  
TL1 C1  C2   SING N N 4  
TL1 N2  HN21 SING N N 5  
TL1 N2  HN22 SING N N 6  
TL1 C2  C3   DOUB Y N 7  
TL1 C2  C20  SING Y N 8  
TL1 C3  C4   SING Y N 9  
TL1 C3  H3   SING N N 10 
TL1 C4  C5   DOUB Y N 11 
TL1 C4  H4   SING N N 12 
TL1 C5  C6   SING Y N 13 
TL1 C5  H5   SING N N 14 
TL1 C6  O1   SING N N 15 
TL1 C6  C20  DOUB Y N 16 
TL1 O1  C7   SING N N 17 
TL1 C7  C8   SING N N 18 
TL1 C7  C19  SING N N 19 
TL1 C7  H7   SING N N 20 
TL1 C8  O2   SING N N 21 
TL1 C8  H81  SING N N 22 
TL1 C8  H82  SING N N 23 
TL1 O2  C9   SING N N 24 
TL1 C9  C10  SING N N 25 
TL1 C9  C19  SING N N 26 
TL1 C9  H9   SING N N 27 
TL1 C10 O3   SING N N 28 
TL1 C10 C18  SING N N 29 
TL1 C10 H10  SING N N 30 
TL1 O3  C11  SING N N 31 
TL1 C11 C12  DOUB Y N 32 
TL1 C11 C17  SING Y N 33 
TL1 C12 C13  SING Y N 34 
TL1 C12 H12  SING N N 35 
TL1 C13 C14  DOUB Y N 36 
TL1 C13 H13  SING N N 37 
TL1 C14 C15  SING Y N 38 
TL1 C14 H14  SING N N 39 
TL1 C15 C16  SING N N 40 
TL1 C15 C17  DOUB Y N 41 
TL1 C16 N3   DOUB N N 42 
TL1 C16 N4   SING N N 43 
TL1 N3  HN3  SING N N 44 
TL1 N4  HN41 SING N N 45 
TL1 N4  HN42 SING N N 46 
TL1 C17 H17  SING N N 47 
TL1 C18 O4   SING N N 48 
TL1 C18 H181 SING N N 49 
TL1 C18 H182 SING N N 50 
TL1 O4  C19  SING N N 51 
TL1 C19 H19  SING N N 52 
TL1 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 
TL1 SMILES           ACDLabs              10.04 O(c1cc(C(=[N@H])N)ccc1)C3C4OCC(Oc2cc(C(=[N@H])N)ccc2)C4OC3 
TL1 InChI            InChI                1.02b 
InChI=1/C20H22N4O4/c21-19(22)11-3-1-5-13(7-11)27-15-9-25-18-16(10-26-17(15)18)28-14-6-2-4-12(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?/t15-,16+,17+,18+/m0 
TL1 InChIKey         InChI                1.02b IBIUTOFGXGGVKQ-PTQVKSGFDP 
TL1 SMILES_CANONICAL CACTVS               3.341 NC(=N)c1cccc(O[C@@H]2CO[C@@H]3[C@H](CO[C@H]23)Oc4cccc(c4)C(N)=N)c1 
TL1 SMILES           CACTVS               3.341 NC(=N)c1cccc(O[CH]2CO[CH]3[CH](CO[CH]23)Oc4cccc(c4)C(N)=N)c1 
TL1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)O[C@@H]2CO[C@H]3[C@@H]2OC[C@@H]3Oc4cccc(c4)C(=N)N)C(=N)N 
TL1 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)OC2COC3C2OCC3Oc4cccc(c4)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 
TL1 "SYSTEMATIC NAME" ACDLabs              10.04 1,4:3,6-dianhydro-2,5-bis-O-(3-carbamimidoylphenyl)-D-glucitol                                                         
TL1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 3-[[(3R,3aR,6S,6aR)-6-(3-carbamimidoylphenoxy)-2,3,3a,5,6,6a-hexahydrofuro[4,5-b]furan-3-yl]oxy]benzenecarboximidamide 
# 
