data_2AA
# 
_chem_comp.id                                    2AA 
_chem_comp.name                                  "5'-O-{[({[2-({[5-(DIMETHYLAMINO)NAPHTHALEN-1-YL]SULFONYL}AMINO)ETHYL]OXY}PHOSPHINATO)OXY]PHOSPHINATO}CYT" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H31 N5 O13 P2 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-09-26 
_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                        679.530 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     2AA 
_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   Y 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
2AA C13    C13  C 0 1 N N N 2.248  21.240 37.999 -4.901 5.172  -1.089 C13    2AA 1  
2AA N5     N5   N 0 1 N N N 3.362  20.597 37.677 -6.226 4.537  -1.057 N5     2AA 2  
2AA C12    C12  C 0 1 N N N 4.363  20.638 38.548 -6.931 4.971  -2.270 C12    2AA 3  
2AA C11    C11  C 0 1 Y N N 3.478  19.956 36.484 -6.015 3.166  -1.186 C11    2AA 4  
2AA C10    C10  C 0 1 Y N N 3.068  20.645 35.333 -5.389 2.660  -2.305 C10    2AA 5  
2AA "C9'"  C9*  C 0 1 Y N N 3.153  20.065 34.065 -5.174 1.292  -2.443 "C9'"  2AA 6  
2AA "C8'"  C8*  C 0 1 Y N N 3.661  18.778 33.934 -5.575 0.416  -1.480 "C8'"  2AA 7  
2AA "C7'"  C7*  C 0 1 Y N N 4.086  18.071 35.059 -6.217 0.891  -0.324 "C7'"  2AA 8  
2AA "C6'"  C6*  C 0 1 Y N N 4.001  18.648 36.340 -6.436 2.282  -0.169 "C6'"  2AA 9  
2AA "C5'"  C5*  C 0 1 Y N N 4.439  17.896 37.439 -7.077 2.754  0.987  "C5'"  2AA 10 
2AA "C4'"  C4*  C 0 1 Y N N 4.949  16.608 37.264 -7.479 1.872  1.943  "C4'"  2AA 11 
2AA "C3'"  C3*  C 0 1 Y N N 5.037  16.045 35.990 -7.264 0.504  1.792  "C3'"  2AA 12 
2AA "C2'"  C2*  C 0 1 Y N N 4.594  16.782 34.896 -6.641 0.010  0.687  "C2'"  2AA 13 
2AA S1     S1   S 0 1 N N N 4.700  16.101 33.298 -6.381 -1.724 0.517  S1     2AA 14 
2AA "O3'"  O3*  O 0 1 N N N 3.841  14.852 33.201 -6.833 -2.056 -0.789 "O3'"  2AA 15 
2AA "O4'"  O4*  O 0 1 N N N 4.235  17.108 32.269 -6.854 -2.305 1.724  "O4'"  2AA 16 
2AA N4     N4   N 0 1 N N N 6.287  15.763 33.067 -4.745 -1.980 0.506  N4     2AA 17 
2AA "C1'"  C1*  C 0 1 N N N 6.709  16.512 31.887 -3.946 -1.662 1.692  "C1'"  2AA 18 
2AA C9     C9   C 0 1 N N N 6.313  15.654 30.699 -2.581 -2.346 1.585  C9     2AA 19 
2AA "O2'"  O2*  O 0 1 N N N 7.424  14.852 30.385 -1.857 -1.795 0.483  "O2'"  2AA 20 
2AA P2     P2   P 0 1 N N R 7.895  14.937 28.869 -0.439 -2.557 0.431  P2     2AA 21 
2AA "O1'"  O1*  O 0 1 N N N 7.079  15.980 28.175 -0.678 -4.112 0.092  "O1'"  2AA 22 
2AA O9     O9   O 0 1 N N N 9.398  14.979 28.763 0.235  -2.435 1.743  O9     2AA 23 
2AA O8     O8   O 0 1 N N N 7.390  13.463 28.448 0.483  -1.894 -0.710 O8     2AA 24 
2AA P1     P1   P 0 1 N N S 8.313  12.150 28.637 1.986  -2.410 -0.451 P1     2AA 25 
2AA O7     O7   O 0 1 N N N 7.380  11.004 28.818 2.153  -3.898 -1.042 O7     2AA 26 
2AA O6     O6   O 0 1 N N N 9.341  12.081 27.584 2.259  -2.424 1.004  O6     2AA 27 
2AA O5     O5   O 0 1 N N N 9.088  12.331 30.013 3.027  -1.422 -1.182 O5     2AA 28 
2AA C14    C14  C 0 1 N N N 9.509  11.059 30.516 4.337  -1.860 -0.819 C14    2AA 29 
2AA C8     C8   C 0 1 N N R 10.183 11.053 31.877 5.379  -0.959 -1.484 C8     2AA 30 
2AA O2     O2   O 0 1 N N N 10.406 9.626  32.108 5.299  0.368  -0.936 O2     2AA 31 
2AA C7     C7   C 0 1 N N S 11.561 11.696 31.757 6.795  -1.493 -1.195 C7     2AA 32 
2AA O4     O4   O 0 1 N N N 11.608 12.855 32.584 7.472  -1.818 -2.411 O4     2AA 33 
2AA C6     C6   C 0 1 N N R 12.523 10.675 32.318 7.503  -0.313 -0.478 C6     2AA 34 
2AA O3     O3   O 0 1 N N N 12.607 10.872 33.732 8.850  -0.173 -0.936 O3     2AA 35 
2AA C5     C5   C 0 1 N N R 11.836 9.342  32.048 6.642  0.898  -0.918 C5     2AA 36 
2AA N3     N3   N 0 1 Y N N 12.260 8.610  30.809 6.751  1.993  0.050  N3     2AA 37 
2AA C4     C4   C 0 1 Y N N 11.919 8.994  29.488 7.243  3.200  -0.346 C4     2AA 38 
2AA C3     C3   C 0 1 Y N N 12.355 8.228  28.400 7.339  4.204  0.558  C3     2AA 39 
2AA C2     C2   C 0 1 Y N N 13.119 7.085  28.613 6.927  3.969  1.886  C2     2AA 40 
2AA N2     N2   N 0 1 N N N 13.550 6.333  27.601 7.014  4.971  2.825  N2     2AA 41 
2AA N1     N1   N 0 1 Y N N 13.452 6.710  29.904 6.455  2.777  2.225  N1     2AA 42 
2AA C1     C1   C 0 1 Y N N 13.039 7.459  30.991 6.361  1.801  1.323  C1     2AA 43 
2AA O1     O1   O 0 1 N N N 13.360 7.100  32.118 5.923  0.713  1.659  O1     2AA 44 
2AA H131   1H13 H 0 0 N N N 1.378  20.632 37.711 -5.014 6.252  -0.991 H131   2AA 45 
2AA H132   2H13 H 0 0 N N N 2.215  22.203 37.469 -4.297 4.793  -0.265 H132   2AA 46 
2AA H133   3H13 H 0 0 N N N 2.227  21.418 39.084 -4.411 4.942  -2.035 H133   2AA 47 
2AA H121   1H12 H 0 0 N N N 4.320  19.751 39.198 -7.925 4.523  -2.292 H121   2AA 48 
2AA H122   2H12 H 0 0 N N N 4.278  21.547 39.161 -7.022 6.057  -2.268 H122   2AA 49 
2AA H123   3H12 H 0 0 N N N 5.321  20.649 38.007 -6.371 4.655  -3.150 H123   2AA 50 
2AA H10    H10  H 0 1 N N N 2.677  21.647 35.429 -5.062 3.333  -3.084 H10    2AA 51 
2AA "H9'"  H9*  H 0 1 N N N 2.826  20.612 33.193 -4.681 0.918  -3.329 "H9'"  2AA 52 
2AA "H8'"  H8*  H 0 1 N N N 3.727  18.323 32.957 -5.400 -0.642 -1.605 "H8'"  2AA 53 
2AA "H5'"  H5*  H 0 1 N N N 4.381  18.317 38.432 -7.249 3.812  1.118  "H5'"  2AA 54 
2AA "H4'"  H4*  H 0 1 N N N 5.279  16.042 38.123 -7.971 2.238  2.832  "H4'"  2AA 55 
2AA "H3'"  H3*  H 0 1 N N N 5.442  15.053 35.855 -7.592 -0.175 2.565  "H3'"  2AA 56 
2AA HN4    HN4  H 0 1 N N N 6.822  16.040 33.865 -4.316 -2.340 -0.286 HN4    2AA 57 
2AA "H1'1" 1H1* H 0 0 N N N 7.790  16.715 31.900 -3.807 -0.583 1.758  "H1'1" 2AA 58 
2AA "H1'2" 2H1* H 0 0 N N N 6.209  17.491 31.846 -4.462 -2.018 2.584  "H1'2" 2AA 59 
2AA H91    1H9  H 0 1 N N N 6.026  16.280 29.841 -2.020 -2.183 2.506  H91    2AA 60 
2AA H92    2H9  H 0 1 N N N 5.447  15.025 30.954 -2.722 -3.415 1.430  H92    2AA 61 
2AA HO9    HO9  H 0 1 N N N 9.651  14.988 27.847 ?      ?      ?      HO9    2AA 62 
2AA HO6    HO6  H 0 1 N N N 8.922  12.066 26.732 ?      ?      ?      HO6    2AA 63 
2AA H141   1H14 H 0 0 N N N 10.272 10.702 29.809 4.451  -1.809 0.264  H141   2AA 64 
2AA H142   2H14 H 0 0 N N N 8.611  10.429 30.596 4.482  -2.889 -1.151 H142   2AA 65 
2AA H8     H8   H 0 1 N N N 9.602  11.575 32.652 5.208  -0.926 -2.560 H8     2AA 66 
2AA H7     H7   H 0 1 N N N 11.796 11.981 30.721 6.748  -2.363 -0.541 H7     2AA 67 
2AA HO4    HO4  H 0 1 N N N 11.618 12.593 33.497 8.369  -2.087 -2.168 HO4    2AA 68 
2AA H6     H6   H 0 1 N N N 13.533 10.735 31.886 7.473  -0.439 0.604  H6     2AA 69 
2AA HO3    HO3  H 0 1 N N N 12.626 10.029 34.169 9.331  -0.955 -0.631 HO3    2AA 70 
2AA H5     H5   H 0 1 N N N 12.145 8.612  32.811 6.934  1.236  -1.913 H5     2AA 71 
2AA H4     H4   H 0 1 N N N 11.322 9.878  29.320 7.552  3.356  -1.369 H4     2AA 72 
2AA H3     H3   H 0 1 N N N 12.098 8.525  27.394 7.726  5.169  0.267  H3     2AA 73 
2AA HN21   1HN2 H 0 0 N N N 14.102 5.504  27.688 7.360  5.842  2.574  HN21   2AA 74 
2AA HN22   2HN2 H 0 0 N N N 13.232 6.731  26.740 6.730  4.806  3.738  HN22   2AA 75 
# 
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 
2AA C13   N5     SING N N 1  
2AA C13   H131   SING N N 2  
2AA C13   H132   SING N N 3  
2AA C13   H133   SING N N 4  
2AA N5    C12    SING N N 5  
2AA N5    C11    SING N N 6  
2AA C12   H121   SING N N 7  
2AA C12   H122   SING N N 8  
2AA C12   H123   SING N N 9  
2AA C11   C10    DOUB Y N 10 
2AA C11   "C6'"  SING Y N 11 
2AA C10   "C9'"  SING Y N 12 
2AA C10   H10    SING N N 13 
2AA "C9'" "C8'"  DOUB Y N 14 
2AA "C9'" "H9'"  SING N N 15 
2AA "C8'" "C7'"  SING Y N 16 
2AA "C8'" "H8'"  SING N N 17 
2AA "C7'" "C6'"  DOUB Y N 18 
2AA "C7'" "C2'"  SING Y N 19 
2AA "C6'" "C5'"  SING Y N 20 
2AA "C5'" "C4'"  DOUB Y N 21 
2AA "C5'" "H5'"  SING N N 22 
2AA "C4'" "C3'"  SING Y N 23 
2AA "C4'" "H4'"  SING N N 24 
2AA "C3'" "C2'"  DOUB Y N 25 
2AA "C3'" "H3'"  SING N N 26 
2AA "C2'" S1     SING N N 27 
2AA S1    "O3'"  DOUB N N 28 
2AA S1    "O4'"  DOUB N N 29 
2AA S1    N4     SING N N 30 
2AA N4    "C1'"  SING N N 31 
2AA N4    HN4    SING N N 32 
2AA "C1'" C9     SING N N 33 
2AA "C1'" "H1'1" SING N N 34 
2AA "C1'" "H1'2" SING N N 35 
2AA C9    "O2'"  SING N N 36 
2AA C9    H91    SING N N 37 
2AA C9    H92    SING N N 38 
2AA "O2'" P2     SING N N 39 
2AA P2    "O1'"  DOUB N N 40 
2AA P2    O9     SING N N 41 
2AA P2    O8     SING N N 42 
2AA O9    HO9    SING N N 43 
2AA O8    P1     SING N N 44 
2AA P1    O7     DOUB N N 45 
2AA P1    O6     SING N N 46 
2AA P1    O5     SING N N 47 
2AA O6    HO6    SING N N 48 
2AA O5    C14    SING N N 49 
2AA C14   C8     SING N N 50 
2AA C14   H141   SING N N 51 
2AA C14   H142   SING N N 52 
2AA C8    O2     SING N N 53 
2AA C8    C7     SING N N 54 
2AA C8    H8     SING N N 55 
2AA O2    C5     SING N N 56 
2AA C7    O4     SING N N 57 
2AA C7    C6     SING N N 58 
2AA C7    H7     SING N N 59 
2AA O4    HO4    SING N N 60 
2AA C6    O3     SING N N 61 
2AA C6    C5     SING N N 62 
2AA C6    H6     SING N N 63 
2AA O3    HO3    SING N N 64 
2AA C5    N3     SING N N 65 
2AA C5    H5     SING N N 66 
2AA N3    C4     SING Y N 67 
2AA N3    C1     SING Y N 68 
2AA C4    C3     DOUB Y N 69 
2AA C4    H4     SING N N 70 
2AA C3    C2     SING Y N 71 
2AA C3    H3     SING N N 72 
2AA C2    N2     SING N N 73 
2AA C2    N1     DOUB Y N 74 
2AA N2    HN21   SING N N 75 
2AA N2    HN22   SING N N 76 
2AA N1    C1     SING Y N 77 
2AA C1    O1     DOUB N N 78 
# 
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 
2AA SMILES           ACDLabs              10.04 O=S(=O)(c2c1cccc(N(C)C)c1ccc2)NCCOP(=O)(O)OP(=O)(O)OCC4OC(N3C(=O)N=C(N)C=C3)C(O)C4O 
2AA InChI            InChI                1.02b 
;InChI=1/C23H31N5O13P2S/c1-27(2)16-7-3-6-15-14(16)5-4-8-18(15)44(36,37)25-10-12-38-42(32,33)41-43(34,35)39-13-17-20(29)21(30)22(40-17)28-11-9-19(24)26-23(28)31/h3-9,11,17,20-22,25,29-30H,10,12-13H2,1-2H3,(H,32,33)(H,34,35)(H2,24,26,31)/t17-,20-,21-,22-/m1/s1/f/h32,34H,24H2
;
2AA InChIKey         InChI                1.02b OXPWLEWKRGQJQO-OAMLDLGFDB 
2AA SMILES_CANONICAL CACTVS               3.341 CN(C)c1cccc2c1cccc2[S](=O)(=O)NCCO[P@](O)(=O)O[P@](O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N4C=CC(=NC4=O)N 
2AA SMILES           CACTVS               3.341 CN(C)c1cccc2c1cccc2[S](=O)(=O)NCCO[P](O)(=O)O[P](O)(=O)OC[CH]3O[CH]([CH](O)[CH]3O)N4C=CC(=NC4=O)N 
2AA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CN(C)c1cccc2c1cccc2S(=O)(=O)NCCO[P@@](=O)(O)O[P@@](=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=NC4=O)N)O)O 
2AA SMILES           "OpenEye OEToolkits" 1.5.0 CN(C)c1cccc2c1cccc2S(=O)(=O)NCCOP(=O)(O)OP(=O)(O)OCC3C(C(C(O3)N4C=CC(=NC4=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 
2AA "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-[(S)-{[(R)-[2-({[5-(dimethylamino)naphthalen-1-yl]sulfonyl}amino)ethoxy](hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]cytidine"                                                
2AA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] 2-[(5-dimethylaminonaphthalen-1-yl)sulfonylamino]ethyl hydrogen phosphate" 
# 
