data_5CA
# 
_chem_comp.id                                    5CA 
_chem_comp.name                                  "5'-O-(N-(L-CYSTEINYL)-SULFAMOYL)ADENOSINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H19 N7 O7 S2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-01-07 
_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                        449.463 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5CA 
_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        1NJ1 
_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 
5CA N      N    N 0 1 N N N -35.976 -79.826 -41.089 -2.753 3.037  -0.518 N      5CA 1  
5CA CA     CA   C 0 1 N N R -34.520 -79.919 -41.026 -3.451 2.018  0.277  CA     5CA 2  
5CA CB     CB   C 0 1 N N N -33.881 -78.549 -40.980 -4.924 2.407  0.424  CB     5CA 3  
5CA SG     SG   S 0 1 N N N -34.861 -77.405 -40.007 -5.045 4.013  1.258  SG     5CA 4  
5CA C      C    C 0 1 N N N -34.146 -80.651 -39.771 -3.350 0.684  -0.417 C      5CA 5  
5CA O      O    O 0 1 N N N -34.916 -81.110 -38.964 -3.093 0.634  -1.601 O      5CA 6  
5CA N3S    N3S  N 0 1 N N N -32.912 -81.225 -39.893 -3.546 -0.453 0.279  N3S    5CA 7  
5CA S      S    S 0 1 N N N -32.261 -82.296 -38.890 -3.435 -1.919 -0.483 S      5CA 8  
5CA O1S    O1S  O 0 1 N N N -33.181 -83.435 -38.714 -3.636 -2.897 0.529  O1S    5CA 9  
5CA O2S    O2S  O 0 1 N N N -30.916 -82.576 -39.492 -4.205 -1.796 -1.671 O2S    5CA 10 
5CA "O5'"  O5*  O 0 1 N N N -32.040 -81.571 -37.477 -1.993 -2.087 -0.940 "O5'"  5CA 11 
5CA "C5'"  C5*  C 0 1 N N N -31.475 -80.250 -37.387 -1.224 -2.392 0.225  "C5'"  5CA 12 
5CA "C4'"  C4*  C 0 1 N N R -30.327 -80.198 -36.402 0.244  -2.574 -0.167 "C4'"  5CA 13 
5CA "O4'"  O4*  O 0 1 N N N -30.798 -80.442 -35.051 0.788  -1.322 -0.618 "O4'"  5CA 14 
5CA "C3'"  C3*  C 0 1 N N S -29.237 -81.223 -36.630 1.063  -3.018 1.060  "C3'"  5CA 15 
5CA "O3'"  O3*  O 0 1 N N N -28.275 -80.693 -37.544 1.676  -4.288 0.828  "O3'"  5CA 16 
5CA "C2'"  C2*  C 0 1 N N R -28.675 -81.488 -35.242 2.142  -1.914 1.212  "C2'"  5CA 17 
5CA "O2'"  O2*  O 0 1 N N N -27.565 -80.671 -34.924 3.410  -2.484 1.546  "O2'"  5CA 18 
5CA "C1'"  C1*  C 0 1 N N R -29.841 -81.192 -34.316 2.172  -1.292 -0.207 "C1'"  5CA 19 
5CA N9     N9   N 0 1 Y N N -30.532 -82.374 -33.732 2.667  0.086  -0.160 N9     5CA 20 
5CA C8     C8   C 0 1 Y N N -31.191 -83.411 -34.368 1.910  1.210  -0.007 C8     5CA 21 
5CA N7     N7   N 0 1 Y N N -31.709 -84.300 -33.538 2.674  2.264  -0.008 N7     5CA 22 
5CA C5     C5   C 0 1 Y N N -31.376 -83.828 -32.279 3.965  1.884  -0.161 C5     5CA 23 
5CA C6     C6   C 0 1 Y N N -31.632 -84.310 -30.951 5.193  2.564  -0.234 C6     5CA 24 
5CA N6     N6   N 0 1 N N N -32.315 -85.424 -30.689 5.244  3.944  -0.142 N6     5CA 25 
5CA N1     N1   N 0 1 Y N N -31.151 -83.589 -29.888 6.303  1.851  -0.393 N1     5CA 26 
5CA C2     C2   C 0 1 Y N N -30.453 -82.446 -30.130 6.264  0.535  -0.481 C2     5CA 27 
5CA N3     N3   N 0 1 Y N N -30.155 -81.898 -31.336 5.137  -0.144 -0.418 N3     5CA 28 
5CA C4     C4   C 0 1 Y N N -30.646 -82.640 -32.375 3.977  0.482  -0.255 C4     5CA 29 
5CA H      H    H 0 1 N N N -36.280 -79.245 -41.871 -3.208 3.065  -1.418 H      5CA 30 
5CA HN2    HN2  H 0 1 N N N -36.407 -80.750 -41.120 -2.933 3.925  -0.074 HN2    5CA 31 
5CA HA     HA   H 0 1 N N N -34.160 -80.452 -41.937 -2.993 1.951  1.263  HA     5CA 32 
5CA HB1    1HB  H 0 1 N N N -33.687 -78.153 -42.004 -5.382 2.475  -0.563 HB1    5CA 33 
5CA HB2    2HB  H 0 1 N N N -32.829 -78.600 -40.614 -5.442 1.651  1.014  HB2    5CA 34 
5CA HG     HG   H 0 1 N N N -34.460 -76.544 -39.978 -6.381 4.162  1.285  HG     5CA 35 
5CA H3S    H3S  H 0 1 N N N -32.475 -80.852 -40.736 -3.752 -0.413 1.226  H3S    5CA 36 
5CA "H5'1" 1H5* H 0 0 N N N -32.254 -79.490 -37.144 -1.310 -1.575 0.941  "H5'1" 5CA 37 
5CA "H5'2" 2H5* H 0 0 N N N -31.168 -79.870 -38.389 -1.596 -3.312 0.675  "H5'2" 5CA 38 
5CA "H4'"  H4*  H 0 1 N N N -29.906 -79.177 -36.552 0.327  -3.320 -0.958 "H4'"  5CA 39 
5CA "H3'"  H3*  H 0 1 N N N -29.588 -82.175 -37.092 0.430  -3.057 1.947  "H3'"  5CA 40 
5CA H3T    H3T  H 0 1 N N N -27.591 -81.336 -37.687 2.220  -4.482 1.604  H3T    5CA 41 
5CA "H2'"  H2*  H 0 1 N N N -28.287 -82.530 -35.156 1.843  -1.175 1.954  "H2'"  5CA 42 
5CA "HO'2" 2HO* H 0 0 N N N -27.214 -80.836 -34.057 3.325  -2.852 2.436  "HO'2" 5CA 43 
5CA "H1'"  H1*  H 0 1 N N N -29.404 -80.647 -33.447 2.785  -1.895 -0.878 "H1'"  5CA 44 
5CA H8     H8   H 0 1 N N N -31.296 -83.521 -35.460 0.836  1.223  0.100  H8     5CA 45 
5CA H61    1H6  H 0 1 N N N -31.865 -86.181 -31.203 4.427  4.453  -0.025 H61    5CA 46 
5CA H62    2H6  H 0 1 N N N -32.497 -85.766 -29.746 6.098  4.402  -0.193 H62    5CA 47 
5CA H2     H2   H 0 1 N N N -30.086 -81.900 -29.245 7.190  -0.006 -0.610 H2     5CA 48 
# 
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 
5CA N     CA     SING N N 1  
5CA N     H      SING N N 2  
5CA N     HN2    SING N N 3  
5CA CA    CB     SING N N 4  
5CA CA    C      SING N N 5  
5CA CA    HA     SING N N 6  
5CA CB    SG     SING N N 7  
5CA CB    HB1    SING N N 8  
5CA CB    HB2    SING N N 9  
5CA SG    HG     SING N N 10 
5CA C     O      DOUB N N 11 
5CA C     N3S    SING N N 12 
5CA N3S   S      SING N N 13 
5CA N3S   H3S    SING N N 14 
5CA S     O1S    DOUB N N 15 
5CA S     O2S    DOUB N N 16 
5CA S     "O5'"  SING N N 17 
5CA "O5'" "C5'"  SING N N 18 
5CA "C5'" "C4'"  SING N N 19 
5CA "C5'" "H5'1" SING N N 20 
5CA "C5'" "H5'2" SING N N 21 
5CA "C4'" "O4'"  SING N N 22 
5CA "C4'" "C3'"  SING N N 23 
5CA "C4'" "H4'"  SING N N 24 
5CA "O4'" "C1'"  SING N N 25 
5CA "C3'" "O3'"  SING N N 26 
5CA "C3'" "C2'"  SING N N 27 
5CA "C3'" "H3'"  SING N N 28 
5CA "O3'" H3T    SING N N 29 
5CA "C2'" "O2'"  SING N N 30 
5CA "C2'" "C1'"  SING N N 31 
5CA "C2'" "H2'"  SING N N 32 
5CA "O2'" "HO'2" SING N N 33 
5CA "C1'" N9     SING N N 34 
5CA "C1'" "H1'"  SING N N 35 
5CA N9    C8     SING Y N 36 
5CA N9    C4     SING Y N 37 
5CA C8    N7     DOUB Y N 38 
5CA C8    H8     SING N N 39 
5CA N7    C5     SING Y N 40 
5CA C5    C6     DOUB Y N 41 
5CA C5    C4     SING Y N 42 
5CA C6    N6     SING N N 43 
5CA C6    N1     SING Y N 44 
5CA N6    H61    SING N N 45 
5CA N6    H62    SING N N 46 
5CA N1    C2     DOUB Y N 47 
5CA C2    N3     SING Y N 48 
5CA C2    H2     SING N N 49 
5CA N3    C4     DOUB Y N 50 
# 
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 
5CA SMILES           ACDLabs              10.04 O=C(NS(=O)(=O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O)C(N)CS                                                                                                                                                
5CA InChI            InChI                1.02b InChI=1/C13H19N7O7S2/c14-5(2-28)12(23)19-29(24,25)26-1-6-8(21)9(22)13(27-6)20-4-18-7-10(15)16-3-17-11(7)20/h3-6,8-9,13,21-22,28H,1-2,14H2,(H,19,23)(H2,15,16,17)/t5-,6+,8+,9+,13+/m0/s1/f/h19H,15H2 
5CA InChIKey         InChI                1.02b FTSDEWPMACCNGN-JIYPHCENDY                                                                                                                                                                           
5CA SMILES_CANONICAL CACTVS               3.341 N[C@@H](CS)C(=O)N[S](=O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23                                                                                                                        
5CA SMILES           CACTVS               3.341 N[CH](CS)C(=O)N[S](=O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23                                                                                                                               
5CA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COS(=O)(=O)NC(=O)[C@H](CS)N)O)O)N                                                                                                                    
5CA SMILES           "OpenEye OEToolkits" 1.5.0 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COS(=O)(=O)NC(=O)C(CS)N)O)O)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 
5CA "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-(L-cysteinylsulfamoyl)adenosine"                                                                                 
5CA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl N-[(2R)-2-amino-3-sulfanyl-propanoyl]sulfamate" 
# 
