data_AR1
# 
_chem_comp.id                                    AR1 
_chem_comp.name                                  (2-{[4-({4-[(4-FORMYLAMINO-1-METHYL-1H-IMIDAZOLE-2-CARBONYL)-AMINO]-1-METHYL-1H-IMIDAZOLE-2-CARBONYL}-AMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBONYL]-AMINO}-ETHYL)-DIMETHYL-AMMONIUM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H28 N11 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "TRI-IMIDAZOLE DNA MINOR GROOVE BINDER; AR-1-144" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     1999-07-16 
_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                        486.508 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AR1 
_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        1CYZ 
_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 
AR1 CA   CA   C 0 1 N N N 9.700  3.529   9.439  8.427   -4.340 0.040  CA   AR1 1  
AR1 OA   OA   O 0 1 N N N 10.202 3.923   8.388  9.394   -3.608 0.012  OA   AR1 2  
AR1 N1   N1   N 0 1 N N N 10.277 2.692   10.306 7.185   -3.817 0.043  N1   AR1 3  
AR1 C11  C11  C 0 1 Y N N 11.598 2.149   10.179 7.010   -2.425 0.014  C11  AR1 4  
AR1 N21  N21  N 0 1 Y N N 12.198 1.413   11.128 5.841   -1.784 0.014  N21  AR1 5  
AR1 C31  C31  C 0 1 Y N N 13.471 1.164   10.763 6.059   -0.485 -0.012 C31  AR1 6  
AR1 N41  N41  N 0 1 Y N N 13.669 1.761   9.549  7.408   -0.273 -0.038 N41  AR1 7  
AR1 CN1  CN1  C 0 1 N N N 14.923 1.786   8.777  8.085   1.026  -0.074 CN1  AR1 8  
AR1 C51  C51  C 0 1 Y N N 12.489 2.354   9.188  8.006   -1.496 -0.018 C51  AR1 9  
AR1 C1   C1   C 0 1 N N N 14.460 0.428   11.575 5.022   0.562  -0.021 C1   AR1 10 
AR1 O1   O1   O 0 1 N N N 15.634 0.365   11.223 5.343   1.735  -0.045 O1   AR1 11 
AR1 N2   N2   N 0 1 N N N 13.942 -0.284  12.595 3.719   0.220  -0.002 N2   AR1 12 
AR1 C12  C12  C 0 1 Y N N 14.649 -1.198  13.439 2.732   1.216  -0.011 C12  AR1 13 
AR1 N22  N22  N 0 1 Y N N 14.061 -2.003  14.349 1.415   1.011  -0.001 N22  AR1 14 
AR1 C32  C32  C 0 1 Y N N 14.996 -2.661  15.046 0.795   2.174  -0.010 C32  AR1 15 
AR1 N42  N42  N 0 1 Y N N 16.208 -2.260  14.541 1.735   3.165  -0.036 N42  AR1 16 
AR1 CN2  CN2  C 0 1 N N N 17.527 -2.737  14.962 1.479   4.607  -0.060 CN2  AR1 17 
AR1 C52  C52  C 0 1 Y N N 15.976 -1.355  13.545 2.955   2.560  -0.037 C52  AR1 18 
AR1 C2   C2   C 0 1 N N N 14.739 -3.460  16.258 -0.664  2.372  0.001  C2   AR1 19 
AR1 O2   O2   O 0 1 N N N 15.681 -3.760  16.983 -1.126  3.498  -0.015 O2   AR1 20 
AR1 N3   N3   N 0 1 N N N 13.490 -3.935  16.444 -1.489  1.306  0.027  N3   AR1 21 
AR1 C13  C13  C 0 1 Y N N 13.100 -4.807  17.523 -2.878  1.495  0.037  C13  AR1 22 
AR1 N23  N23  N 0 1 Y N N 11.905 -5.435  17.637 -3.798  0.529  0.058  N23  AR1 23 
AR1 C33  C33  C 0 1 Y N N 11.843 -6.074  18.812 -4.998  1.073  0.064  C33  AR1 24 
AR1 N43  N43  N 0 1 Y N N 13.016 -5.831  19.469 -4.857  2.432  0.039  N43  AR1 25 
AR1 CN3  CN3  C 0 1 N N N 13.374 -6.266  20.828 -5.939  3.419  0.031  CN3  AR1 26 
AR1 C53  C53  C 0 1 Y N N 13.786 -5.063  18.654 -3.521  2.696  0.023  C53  AR1 27 
AR1 C3   C3   C 0 1 N N N 10.778 -6.968  19.271 -6.275  0.341  0.089  C3   AR1 28 
AR1 O3   O3   O 0 1 N N N 10.919 -7.534  20.351 -7.327  0.952  0.088  O3   AR1 29 
AR1 NT   NT   N 0 1 N N N 9.760  -7.236  18.433 -6.279  -1.007 0.112  NT   AR1 30 
AR1 C1T  C1T  C 0 1 N N N 8.752  -8.236  18.772 -7.550  -1.736 0.137  C1T  AR1 31 
AR1 C2T  C2T  C 0 1 N N N 7.675  -7.648  19.742 -7.274  -3.241 0.160  C2T  AR1 32 
AR1 N3T  N3T  N 1 1 N N N 8.026  -8.006  21.150 -8.548  -3.971 0.185  N3T  AR1 33 
AR1 CNT  CNT  C 0 1 N N N 7.636  -7.023  22.175 -9.276  -3.729 -1.068 CNT  AR1 34 
AR1 CMT  CMT  C 0 1 N N N 7.653  -9.376  21.552 -8.285  -5.409 0.328  CMT  AR1 35 
AR1 HA   HA   H 0 1 N N N 8.732  3.908   9.756  8.562   -5.412 0.062  HA   AR1 36 
AR1 HN1  HN1  H 0 1 N N N 9.757  2.488   11.140 6.412   -4.402 0.065  HN1  AR1 37 
AR1 HN11 1HN1 H 0 0 N N N 15.662 2.388   9.308  8.240   1.326  -1.110 HN11 AR1 38 
AR1 HN12 2HN1 H 0 0 N N N 14.746 2.222   7.793  7.469   1.770  0.431  HN12 AR1 39 
AR1 HN13 3HN1 H 0 0 N N N 15.303 0.771   8.659  9.048   0.948  0.430  HN13 AR1 40 
AR1 H51  H51  H 0 1 N N N 12.277 2.802   8.229  9.068   -1.693 -0.026 H51  AR1 41 
AR1 HN2  HN2  H 0 1 N N N 12.953 -0.255  12.728 3.463   -0.716 0.017  HN2  AR1 42 
AR1 HN21 1HN2 H 0 0 N N N 17.540 -3.826  14.920 1.407   4.946  -1.093 HN21 AR1 43 
AR1 HN22 2HN2 H 0 0 N N N 17.722 -2.403  15.980 0.544   4.819  0.459  HN22 AR1 44 
AR1 HN23 3HN2 H 0 0 N N N 18.289 -2.339  14.291 2.297   5.129  0.437  HN23 AR1 45 
AR1 H52  H52  H 0 1 N N N 16.724 -0.884  12.925 3.916   3.051  -0.054 H52  AR1 46 
AR1 HN3  HN3  H 0 1 N N N 12.790 -3.756  15.748 -1.121  0.409  0.040  HN3  AR1 47 
AR1 HN31 1HN3 H 0 0 N N N 12.624 -5.893  21.530 -6.216  3.646  -0.998 HN31 AR1 48 
AR1 HN32 2HN3 H 0 0 N N N 14.350 -5.866  21.098 -6.803  3.016  0.560  HN32 AR1 49 
AR1 HN33 3HN3 H 0 0 N N N 13.399 -7.354  20.870 -5.603  4.330  0.527  HN33 AR1 50 
AR1 H53  H53  H 0 1 N N N 14.793 -4.758  18.872 -3.059  3.672  0.002  H53  AR1 51 
AR1 HT   HT   H 0 1 N N N 9.723  -6.820  17.513 -5.440  -1.494 0.113  HT   AR1 52 
AR1 H1T1 1H1T H 0 0 N N N 9.283  -9.027  19.322 -8.112  -1.455 1.027  H1T1 AR1 53 
AR1 H1T2 2H1T H 0 0 N N N 8.363  -8.627  17.802 -8.129  -1.486 -0.752 H1T2 AR1 54 
AR1 H2T1 1H2T H 0 0 N N N 6.659  -8.034  19.466 -6.712  -3.521 -0.731 H2T1 AR1 55 
AR1 H2T2 2H2T H 0 0 N N N 7.730  -6.542  19.604 -6.695  -3.490 1.049  H2T2 AR1 56 
AR1 HNT  HNT  H 0 1 N N N 9.025  -7.988  21.183 -9.104  -3.652 0.964  HNT  AR1 57 
AR1 HNT1 1HNT H 0 0 N N N 7.961  -6.018  21.897 -10.222 -4.271 -1.050 HNT1 AR1 58 
AR1 HNT2 2HNT H 0 0 N N N 8.126  -7.277  23.123 -9.471  -2.662 -1.174 HNT2 AR1 59 
AR1 HNT3 3HNT H 0 0 N N N 6.559  -7.019  22.340 -8.676  -4.074 -1.910 HNT3 AR1 60 
AR1 HMT1 1HMT H 0 0 N N N 6.613  -9.595  21.309 -7.745  -5.589 1.257  HMT1 AR1 61 
AR1 HMT2 2HMT H 0 0 N N N 7.792  -9.509  22.631 -9.231  -5.952 0.346  HMT2 AR1 62 
AR1 HMT3 3HMT H 0 0 N N N 8.292  -10.107 21.048 -7.685  -5.754 -0.514 HMT3 AR1 63 
# 
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 
AR1 CA  OA   DOUB N N 1  
AR1 CA  N1   SING N N 2  
AR1 CA  HA   SING N N 3  
AR1 N1  C11  SING N N 4  
AR1 N1  HN1  SING N N 5  
AR1 C11 N21  SING Y N 6  
AR1 C11 C51  DOUB Y N 7  
AR1 N21 C31  DOUB Y N 8  
AR1 C31 N41  SING Y N 9  
AR1 C31 C1   SING N N 10 
AR1 N41 CN1  SING N N 11 
AR1 N41 C51  SING Y N 12 
AR1 CN1 HN11 SING N N 13 
AR1 CN1 HN12 SING N N 14 
AR1 CN1 HN13 SING N N 15 
AR1 C51 H51  SING N N 16 
AR1 C1  O1   DOUB N N 17 
AR1 C1  N2   SING N N 18 
AR1 N2  C12  SING N N 19 
AR1 N2  HN2  SING N N 20 
AR1 C12 N22  SING Y N 21 
AR1 C12 C52  DOUB Y N 22 
AR1 N22 C32  DOUB Y N 23 
AR1 C32 N42  SING Y N 24 
AR1 C32 C2   SING N N 25 
AR1 N42 CN2  SING N N 26 
AR1 N42 C52  SING Y N 27 
AR1 CN2 HN21 SING N N 28 
AR1 CN2 HN22 SING N N 29 
AR1 CN2 HN23 SING N N 30 
AR1 C52 H52  SING N N 31 
AR1 C2  O2   DOUB N N 32 
AR1 C2  N3   SING N N 33 
AR1 N3  C13  SING N N 34 
AR1 N3  HN3  SING N N 35 
AR1 C13 N23  SING Y N 36 
AR1 C13 C53  DOUB Y N 37 
AR1 N23 C33  DOUB Y N 38 
AR1 C33 N43  SING Y N 39 
AR1 C33 C3   SING N N 40 
AR1 N43 CN3  SING N N 41 
AR1 N43 C53  SING Y N 42 
AR1 CN3 HN31 SING N N 43 
AR1 CN3 HN32 SING N N 44 
AR1 CN3 HN33 SING N N 45 
AR1 C53 H53  SING N N 46 
AR1 C3  O3   DOUB N N 47 
AR1 C3  NT   SING N N 48 
AR1 NT  C1T  SING N N 49 
AR1 NT  HT   SING N N 50 
AR1 C1T C2T  SING N N 51 
AR1 C1T H1T1 SING N N 52 
AR1 C1T H1T2 SING N N 53 
AR1 C2T N3T  SING N N 54 
AR1 C2T H2T1 SING N N 55 
AR1 C2T H2T2 SING N N 56 
AR1 N3T CNT  SING N N 57 
AR1 N3T CMT  SING N N 58 
AR1 N3T HNT  SING N N 59 
AR1 CNT HNT1 SING N N 60 
AR1 CNT HNT2 SING N N 61 
AR1 CNT HNT3 SING N N 62 
AR1 CMT HMT1 SING N N 63 
AR1 CMT HMT2 SING N N 64 
AR1 CMT HMT3 SING N N 65 
# 
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 
AR1 SMILES           ACDLabs              10.04 O=C(c1nc(NC=O)cn1C)Nc3nc(C(=O)Nc2nc(C(=O)NCC[NH+](C)C)n(c2)C)n(c3)C 
AR1 InChI            InChI                1.02b 
InChI=1/C20H27N11O4/c1-28(2)7-6-21-18(33)15-24-13(9-30(15)4)26-20(35)17-25-14(10-31(17)5)27-19(34)16-23-12(22-11-32)8-29(16)3/h8-11H,6-7H2,1-5H3,(H,21,33)(H,22,32)(H,26,35)(H,27,34)/p+1/fC20H28N11O4/h21-22,26-28H/q+1 
AR1 InChIKey         InChI                1.02b PFRKDKQPQSBYQX-PYROEXSMCN 
AR1 SMILES_CANONICAL CACTVS               3.341 Cn1cc(NC=O)nc1C(=O)Nc2cn(C)c(n2)C(=O)Nc3cn(C)c(n3)C(=O)NCC[NH+](C)C 
AR1 SMILES           CACTVS               3.341 Cn1cc(NC=O)nc1C(=O)Nc2cn(C)c(n2)C(=O)Nc3cn(C)c(n3)C(=O)NCC[NH+](C)C 
AR1 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cn1cc(nc1C(=O)Nc2cn(c(n2)C(=O)Nc3cn(c(n3)C(=O)NCC[NH+](C)C)C)C)NC=O 
AR1 SMILES           "OpenEye OEToolkits" 1.5.0 Cn1cc(nc1C(=O)Nc2cn(c(n2)C(=O)Nc3cn(c(n3)C(=O)NCC[NH+](C)C)C)C)NC=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 
AR1 "SYSTEMATIC NAME" ACDLabs              10.04 2-({[4-({[4-({[4-(formylamino)-1-methyl-1H-imidazol-2-yl]carbonyl}amino)-1-methyl-1H-imidazol-2-yl]carbonyl}amino)-1-methyl-1H-imidazol-2-yl]carbonyl}amino)-N,N-dimethylethanaminium 
AR1 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[[4-[[4-[(4-formamido-1-methyl-imidazol-2-yl)carbonylamino]-1-methyl-imidazol-2-yl]carbonylamino]-1-methyl-imidazol-2-yl]carbonylamino]ethyl-dimethyl-azanium                       
# 
