data_DOF
# 
_chem_comp.id                                    DOF 
_chem_comp.name                                  "(S)-2-(4-NITROBENZYL)-1,4,7,10-TETRAAZACYCLODODECANE-N,N',N'',N'''-TETRAACETATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H33 N5 O10" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-12-12 
_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                        539.536 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DOF 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1NC4 
_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 
DOF C1   C1   C 0  1 N N S -11.933 14.594 35.990 -1.075 2.622  5.254  C1   DOF 1  
DOF C2   C2   C 0  1 N N N -12.552 13.432 36.764 -0.163 3.292  4.195  C2   DOF 2  
DOF C3   C3   C 0  1 N N N -12.434 11.779 38.480 -0.967 3.302  1.882  C3   DOF 3  
DOF C4   C4   C 0  1 N N N -11.386 10.748 38.282 -1.870 2.048  1.879  C4   DOF 4  
DOF C5   C5   C 0  1 N N N -9.191  10.217 37.576 -0.389 0.290  0.986  C5   DOF 5  
DOF C6   C6   C 0  1 N N N -8.700  10.895 36.344 -0.578 -1.045 1.749  C6   DOF 6  
DOF C7   C7   C 0  1 N N N -8.536  12.999 35.129 -0.198 -0.281 4.050  C7   DOF 7  
DOF C8   C8   C 0  1 N N N -9.967  13.479 34.949 -0.932 0.158  5.335  C8   DOF 8  
DOF C9   C9   C 0  1 N N N -9.865  15.886 35.768 0.890  1.493  6.288  C9   DOF 9  
DOF C10  C10  C 0  1 N N N -8.480  16.132 36.345 1.185  0.405  7.275  C10  DOF 10 
DOF C11  C11  C 0  1 N N N -12.636 14.101 39.113 -0.410 5.367  2.984  C11  DOF 11 
DOF C12  C12  C 0  1 N N N -12.007 15.500 39.108 -1.269 6.097  1.997  C12  DOF 12 
DOF C13  C13  C 0  1 N N N -9.510  10.773 39.869 -1.697 1.676  -0.517 C13  DOF 13 
DOF C14  C14  C 0  1 N N N -10.170 11.585 41.023 -1.646 0.593  -1.550 C14  DOF 14 
DOF C15  C15  C 0  1 N N N -6.767  12.523 36.664 -1.436 -2.315 3.606  C15  DOF 15 
DOF C16  C16  C 0  1 N N N -6.318  12.371 38.136 -2.465 -2.916 2.698  C16  DOF 16 
DOF C17  C17  C 0  1 N N N -12.692 14.728 34.582 -1.486 3.652  6.321  C17  DOF 17 
DOF C18  C18  C 0  1 Y N N -14.218 14.937 34.723 -2.753 3.243  7.013  C18  DOF 18 
DOF C19  C19  C 0  1 Y N N -15.152 14.144 33.982 -3.979 3.655  6.503  C19  DOF 19 
DOF C20  C20  C 0  1 Y N N -16.560 14.340 34.141 -5.157 3.274  7.146  C20  DOF 20 
DOF C21  C21  C 0  1 Y N N -17.102 15.338 35.051 -5.101 2.484  8.294  C21  DOF 21 
DOF C22  C22  C 0  1 Y N N -16.133 16.123 35.780 -3.867 2.075  8.800  C22  DOF 22 
DOF C23  C23  C 0  1 Y N N -14.737 15.931 35.622 -2.689 2.455  8.157  C23  DOF 23 
DOF N1   N1   N 0  1 N N N -10.426 14.497 36.003 -0.522 1.435  5.940  N1   DOF 24 
DOF N2   N2   N 0  1 N N N -12.019 13.158 38.112 -0.961 4.022  3.180  N2   DOF 25 
DOF N3   N3   N 0  1 N N N -9.961  11.105 38.487 -1.633 1.061  0.809  N3   DOF 26 
DOF N4   N4   N 0  1 N N N -8.266  12.343 36.431 -1.111 -0.970 3.119  N4   DOF 27 
DOF N5   N5   N 1  1 N N N -18.476 15.532 35.218 -6.300 2.097  8.948  N5   DOF 28 
DOF O1   O1   O 0  1 N N N -8.058  15.365 37.200 0.404  -0.071 8.085  O1   DOF 29 
DOF O2   O2   O 0  1 N N N -7.825  17.097 35.916 2.476  0.003  7.148  O2   DOF 30 
DOF O3   O3   O 0  1 N N N -10.736 15.588 39.061 -2.470 5.948  1.829  O3   DOF 31 
DOF O4   O4   O 0  1 N N N -12.745 16.499 39.142 -0.514 6.978  1.290  O4   DOF 32 
DOF O5   O5   O 0  1 N N N -10.454 12.734 40.777 -2.078 -0.544 -1.433 O5   DOF 33 
DOF O6   O6   O 0  1 N N N -10.318 10.974 42.159 -1.038 1.054  -2.674 O6   DOF 34 
DOF O7   O7   O 0  1 N N N -7.183  12.484 39.030 -3.308 -2.310 2.053  O7   DOF 35 
DOF O8   O8   O 0  1 N N N -5.120  12.136 38.354 -2.336 -4.268 2.684  O8   DOF 36 
DOF O9   O9   O 0  1 N N N -19.257 14.825 34.563 -6.228 1.386  9.980  O9   DOF 37 
DOF O10  O10  O -1 1 N N N -18.858 16.403 36.017 -7.400 2.475  8.477  O10  DOF 38 
DOF HC1  HC1  H 0  1 N N N -12.093 15.586 36.474 -2.025 2.337  4.789  HC1  DOF 39 
DOF HC21 1HC2 H 0  0 N N N -12.495 12.505 36.148 0.509  3.985  4.722  HC21 DOF 40 
DOF HC22 2HC2 H 0  0 N N N -13.656 13.574 36.824 0.510  2.580  3.712  HC22 DOF 41 
DOF HC31 1HC3 H 0  0 N N N -12.810 11.754 39.529 0.062  3.064  1.585  HC31 DOF 42 
DOF HC32 2HC3 H 0  0 N N N -13.365 11.496 37.936 -1.355 3.978  1.108  HC32 DOF 43 
DOF HC41 1HC4 H 0  0 N N N -11.501 10.316 37.261 -1.827 1.529  2.833  HC41 DOF 44 
DOF HC42 2HC4 H 0  0 N N N -11.628 9.868  38.922 -2.913 2.385  1.804  HC42 DOF 45 
DOF HC51 1HC5 H 0  0 N N N -8.346  9.734  38.121 0.413  0.890  1.428  HC51 DOF 46 
DOF HC52 2HC5 H 0  0 N N N -9.787  9.312  37.314 -0.010 0.002  -0.005 HC52 DOF 47 
DOF HC61 1HC6 H 0  0 N N N -9.474  10.798 35.547 -1.265 -1.658 1.149  HC61 DOF 48 
DOF HC62 2HC6 H 0  0 N N N -7.866  10.295 35.911 0.382  -1.578 1.754  HC62 DOF 49 
DOF HC71 1HC7 H 0  0 N N N -7.821  13.838 34.962 0.220  0.594  3.559  HC71 DOF 50 
DOF HC72 2HC7 H 0  0 N N N -8.243  12.328 34.288 0.661  -0.915 4.303  HC72 DOF 51 
DOF HC81 1HC8 H 0  0 N N N -10.668 12.612 34.912 -2.017 0.189  5.166  HC81 DOF 52 
DOF HC82 2HC8 H 0  0 N N N -10.116 13.887 33.922 -0.801 -0.633 6.087  HC82 DOF 53 
DOF HC91 1HC9 H 0  0 N N N -9.874  16.124 34.679 1.105  2.466  6.738  HC91 DOF 54 
DOF HC92 2HC9 H 0  0 N N N -10.579 16.656 36.143 1.487  1.347  5.384  HC92 DOF 55 
DOF H111 1H11 H 0  0 N N N -13.739 14.165 38.966 0.607  5.281  2.593  H111 DOF 56 
DOF H112 2H11 H 0  0 N N N -12.610 13.661 40.137 -0.411 5.896  3.941  H112 DOF 57 
DOF H131 1H13 H 0  0 N N N -9.639  9.681  40.055 -0.840 2.343  -0.640 H131 DOF 58 
DOF H132 2H13 H 0  0 N N N -8.400  10.860 39.934 -2.633 2.233  -0.607 H132 DOF 59 
DOF H151 1H15 H 0  0 N N N -6.188  11.830 36.010 -1.840 -2.238 4.619  H151 DOF 60 
DOF H152 2H15 H 0  0 N N N -6.427  13.503 36.255 -0.531 -2.927 3.598  H152 DOF 61 
DOF H171 1H17 H 0  0 N N N -12.472 13.851 33.930 -1.609 4.626  5.845  H171 DOF 62 
DOF H172 2H17 H 0  0 N N N -12.238 15.537 33.964 -0.674 3.756  7.044  H172 DOF 63 
DOF H19  H19  H 0  1 N N N -14.783 13.375 33.282 -4.032 4.270  5.609  H19  DOF 64 
DOF H20  H20  H 0  1 N N N -17.243 13.708 33.549 -6.112 3.600  6.741  H20  DOF 65 
DOF H22  H22  H 0  1 N N N -16.473 16.900 36.485 -3.810 1.459  9.694  H22  DOF 66 
DOF H23  H23  H 0  1 N N N -14.046 16.563 36.206 -1.732 2.131  8.558  H23  DOF 67 
DOF HO1  HO1  H 0  1 N N N -10.693 11.572 42.794 -0.989 0.366  -3.372 HO1  DOF 68 
DOF HO2  HO2  H 0  1 N N N -6.981  17.127 36.352 2.700  -0.711 7.782  HO2  DOF 69 
DOF HO3  HO3  H 0  1 N N N -12.214 17.286 39.127 -1.050 7.473  0.634  HO3  DOF 70 
DOF HO4  HO4  H 0  1 N N N -4.977  12.059 39.290 -2.998 -4.692 2.096  HO4  DOF 71 
# 
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 
DOF C1  C2   SING N N 1  
DOF C1  C17  SING N N 2  
DOF C1  N1   SING N N 3  
DOF C1  HC1  SING N N 4  
DOF C2  N2   SING N N 5  
DOF C2  HC21 SING N N 6  
DOF C2  HC22 SING N N 7  
DOF C3  C4   SING N N 8  
DOF C3  N2   SING N N 9  
DOF C3  HC31 SING N N 10 
DOF C3  HC32 SING N N 11 
DOF C4  N3   SING N N 12 
DOF C4  HC41 SING N N 13 
DOF C4  HC42 SING N N 14 
DOF C5  C6   SING N N 15 
DOF C5  N3   SING N N 16 
DOF C5  HC51 SING N N 17 
DOF C5  HC52 SING N N 18 
DOF C6  N4   SING N N 19 
DOF C6  HC61 SING N N 20 
DOF C6  HC62 SING N N 21 
DOF C7  C8   SING N N 22 
DOF C7  N4   SING N N 23 
DOF C7  HC71 SING N N 24 
DOF C7  HC72 SING N N 25 
DOF C8  N1   SING N N 26 
DOF C8  HC81 SING N N 27 
DOF C8  HC82 SING N N 28 
DOF C9  C10  SING N N 29 
DOF C9  N1   SING N N 30 
DOF C9  HC91 SING N N 31 
DOF C9  HC92 SING N N 32 
DOF C10 O1   DOUB N N 33 
DOF C10 O2   SING N N 34 
DOF C11 C12  SING N N 35 
DOF C11 N2   SING N N 36 
DOF C11 H111 SING N N 37 
DOF C11 H112 SING N N 38 
DOF C12 O3   DOUB N N 39 
DOF C12 O4   SING N N 40 
DOF C13 C14  SING N N 41 
DOF C13 N3   SING N N 42 
DOF C13 H131 SING N N 43 
DOF C13 H132 SING N N 44 
DOF C14 O5   DOUB N N 45 
DOF C14 O6   SING N N 46 
DOF C15 C16  SING N N 47 
DOF C15 N4   SING N N 48 
DOF C15 H151 SING N N 49 
DOF C15 H152 SING N N 50 
DOF C16 O7   DOUB N N 51 
DOF C16 O8   SING N N 52 
DOF C17 C18  SING N N 53 
DOF C17 H171 SING N N 54 
DOF C17 H172 SING N N 55 
DOF C18 C19  DOUB Y N 56 
DOF C18 C23  SING Y N 57 
DOF C19 C20  SING Y N 58 
DOF C19 H19  SING N N 59 
DOF C20 C21  DOUB Y N 60 
DOF C20 H20  SING N N 61 
DOF C21 C22  SING Y N 62 
DOF C21 N5   SING N N 63 
DOF C22 C23  DOUB Y N 64 
DOF C22 H22  SING N N 65 
DOF C23 H23  SING N N 66 
DOF N5  O9   DOUB N N 67 
DOF N5  O10  SING N N 68 
DOF HO1 O6   SING N N 69 
DOF HO2 O2   SING N N 70 
DOF HO3 O4   SING N N 71 
DOF HO4 O8   SING N N 72 
# 
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 
DOF SMILES           ACDLabs              10.04 [O-][N+](=O)c1ccc(cc1)CC2N(CCN(CCN(CCN(CC(=O)O)C2)CC(=O)O)CC(=O)O)CC(=O)O 
DOF InChI            InChI                1.02b 
InChI=1/C23H33N5O10/c29-20(30)13-24-5-6-25(14-21(31)32)9-10-27(16-23(35)36)19(12-26(8-7-24)15-22(33)34)11-17-1-3-18(4-2-17)28(37)38/h1-4,19H,5-16H2,(H,29,30)(H,31,32)(H,33,34)(H,35,36)/t19-/m0/s1/f/h29,31,33,35H 
DOF InChIKey         InChI                1.02b SQWOBSHRAUJBNP-UNUAGFGNDA 
DOF SMILES_CANONICAL CACTVS               3.341 OC(=O)CN1CCN(CCN(CC(O)=O)[C@H](CN(CC1)CC(O)=O)Cc2ccc(cc2)[N+]([O-])=O)CC(O)=O 
DOF SMILES           CACTVS               3.341 OC(=O)CN1CCN(CCN(CC(O)=O)[CH](CN(CC1)CC(O)=O)Cc2ccc(cc2)[N+]([O-])=O)CC(O)=O 
DOF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C[C@H]2C[N@](CC[N@](CC[N@](CC[N@]2CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O)[N+](=O)[O-] 
DOF SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1CC2CN(CCN(CCN(CCN2CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O)[N+](=O)[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 
DOF "SYSTEMATIC NAME" ACDLabs              10.04 
;2,2',2'',2'''-[(2S)-2-(4-nitrobenzyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl]tetraacetic acid
;
DOF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[(1S,2S,4S,7S,10R)-4,7,10-tris(carboxymethyl)-2-[(4-nitrophenyl)methyl]-1,4,7,10-tetrazacyclododec-1-yl]ethanoic acid" 
# 
