data_WSA
# 
_chem_comp.id                                    WSA 
_chem_comp.name                                  "5'-O-[(L-TRYPTOPHYLAMINO)SULFONYL]ADENOSINE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H24 N8 O7 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-07-12 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        532.530 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     WSA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_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 
WSA CD2    CD2    C 0 1 Y N N 62.030 -6.293  77.706 -5.680 1.368  0.086  CD2    WSA 1  
WSA CE3    CE3    C 0 1 Y N N 62.297 -6.296  76.341 -5.600 1.972  -1.170 CE3    WSA 2  
WSA CZ3    CZ3    C 0 1 Y N N 62.927 -5.203  75.763 -6.217 3.172  -1.386 CZ3    WSA 3  
WSA CH2    CH2    C 0 1 Y N N 63.292 -4.115  76.548 -6.923 3.796  -0.366 CH2    WSA 4  
WSA CZ2    CZ2    C 0 1 Y N N 63.024 -4.113  77.911 -7.014 3.217  0.881  CZ2    WSA 5  
WSA CE2    CE2    C 0 1 Y N N 62.390 -5.205  78.484 -6.394 1.996  1.123  CE2    WSA 6  
WSA N11    N11    N 0 1 Y N N 62.018 -5.475  79.734 -6.303 1.181  2.230  N11    WSA 7  
WSA CD1    CD1    C 0 1 Y N N 61.442 -6.671  79.772 -5.562 0.071  1.930  CD1    WSA 8  
WSA CG     CG     C 0 1 Y N N 61.438 -7.206  78.556 -5.161 0.120  0.650  CG     WSA 9  
WSA CB     CB     C 0 1 N N N 60.961 -8.613  78.194 -4.330 -0.912 -0.069 CB     WSA 10 
WSA CA     CA     C 0 1 N N S 59.596 -8.629  77.507 -2.855 -0.510 -0.012 CA     WSA 11 
WSA NH3    NH3    N 0 1 N N N 58.585 -8.018  78.386 -2.659 0.738  -0.761 NH3    WSA 12 
WSA C      C      C 0 1 N N N 59.222 -10.085 77.245 -2.013 -1.600 -0.623 C      WSA 13 
WSA O      O      O 0 1 N N N 58.759 -10.769 78.163 -1.612 -1.490 -1.762 O      WSA 14 
WSA NS     NS     N 0 1 N N N 59.425 -10.572 76.025 -1.707 -2.698 0.097  NS     WSA 15 
WSA S      S      S 0 1 N N N 59.539 -12.202 76.077 -0.782 -3.897 -0.574 S      WSA 16 
WSA O1S    O1S    O 0 1 N N N 60.438 -12.619 77.204 -0.611 -4.884 0.434  O1S    WSA 17 
WSA O2S    O2S    O 0 1 N N N 58.179 -12.805 76.277 -1.349 -4.176 -1.847 O2S    WSA 18 
WSA "O5'"  "O5'"  O 0 1 N N N 60.086 -12.640 74.829 0.596  -3.308 -0.837 "O5'"  WSA 19 
WSA "C5'"  "C5'"  C 0 1 N N N 61.427 -12.269 74.490 1.392  -3.144 0.338  "C5'"  WSA 20 
WSA "C4'"  "C4'"  C 0 1 N N R 61.524 -11.738 73.057 2.749  -2.548 -0.043 "C4'"  WSA 21 
WSA "O4'"  "O4'"  O 0 1 N N N 60.893 -12.688 72.178 2.574  -1.208 -0.533 "O4'"  WSA 22 
WSA "C3'"  "C3'"  C 0 1 N N S 60.761 -10.418 72.901 3.654  -2.466 1.201  "C3'"  WSA 23 
WSA "O3'"  "O3'"  O 0 1 N N N 61.497 -9.535  72.049 4.839  -3.241 1.009  "O3'"  WSA 24 
WSA "C2'"  "C2'"  C 0 1 N N R 59.470 -10.871 72.221 4.003  -0.963 1.319  "C2'"  WSA 25 
WSA "O2'"  "O2'"  O 0 1 N N N 58.954 -9.798  71.430 5.375  -0.784 1.674  "O2'"  WSA 26 
WSA "C1'"  "C1'"  C 0 1 N N R 60.050 -11.936 71.291 3.734  -0.453 -0.120 "C1'"  WSA 27 
WSA N9     N9     N 0 1 Y N N 58.989 -12.812 70.745 3.440  0.982  -0.113 N9     WSA 28 
WSA C8     C8     C 0 1 Y N N 58.084 -13.478 71.464 2.208  1.552  0.009  C8     WSA 29 
WSA N7     N7     N 0 1 Y N N 57.336 -14.228 70.665 2.313  2.849  -0.023 N7     WSA 30 
WSA C5     C5     C 0 1 Y N N 57.764 -14.040 69.410 3.615  3.192  -0.168 C5     WSA 31 
WSA C4     C4     C 0 1 Y N N 58.810 -13.132 69.470 4.355  1.998  -0.222 C4     WSA 32 
WSA N3     N3     N 0 1 Y N N 59.422 -12.766 68.330 5.675  2.062  -0.358 N3     WSA 33 
WSA C2     C2     C 0 1 Y N N 59.035 -13.268 67.173 6.286  3.225  -0.438 C2     WSA 34 
WSA N1     N1     N 0 1 Y N N 58.044 -14.137 67.083 5.635  4.373  -0.389 N1     WSA 35 
WSA C6     C6     C 0 1 Y N N 57.388 -14.546 68.183 4.312  4.409  -0.264 C6     WSA 36 
WSA N6     N6     N 0 1 N N N 56.404 -15.440 68.080 3.638  5.616  -0.212 N6     WSA 37 
WSA HE3    HE3    H 0 1 N N N 62.016 -7.144  75.734 -5.052 1.493  -1.968 HE3    WSA 38 
WSA HZ3    HZ3    H 0 1 N N N 63.134 -5.197  74.703 -6.155 3.640  -2.357 HZ3    WSA 39 
WSA HH2    HH2    H 0 1 N N N 63.786 -3.268  76.096 -7.406 4.744  -0.552 HH2    WSA 40 
WSA HZ2    HZ2    H 0 1 N N N 63.307 -3.267  78.520 -7.566 3.710  1.668  HZ2    WSA 41 
WSA HN11   HN11   H 0 0 N N N 62.151 -4.872  80.520 -6.704 1.368  3.093  HN11   WSA 42 
WSA HD1    HD1    H 0 1 N N N 61.038 -7.138  80.658 -5.338 -0.729 2.620  HD1    WSA 43 
WSA HB1    1HB    H 0 1 N N N 61.696 -9.060  77.509 -4.461 -1.882 0.410  HB1    WSA 44 
WSA HB2    2HB    H 0 1 N N N 60.863 -9.178  79.133 -4.650 -0.975 -1.109 HB2    WSA 45 
WSA HA     HA     H 0 1 N N N 59.637 -8.060  76.566 -2.559 -0.361 1.026  HA     WSA 46 
WSA HH31   1HH3   H 0 0 N N N 58.974 -7.879  79.297 -2.926 0.626  -1.728 HH31   WSA 47 
WSA HH32   2HH3   H 0 0 N N N 58.303 -7.137  78.007 -3.162 1.500  -0.333 HH32   WSA 48 
WSA HNS    HNS    H 0 1 N N N 59.498 -10.020 75.194 -2.029 -2.786 1.008  HNS    WSA 49 
WSA "H5'1" "1H5'" H 0 0 N N N 61.761 -11.481 75.182 0.883  -2.474 1.031  "H5'1" WSA 50 
WSA "H5'2" "2H5'" H 0 0 N N N 62.061 -13.164 74.568 1.542  -4.113 0.814  "H5'2" WSA 51 
WSA "H4'"  "H4'"  H 0 1 N N N 62.587 -11.584 72.819 3.222  -3.163 -0.809 "H4'"  WSA 52 
WSA "H3'"  "H3'"  H 0 1 N N N 60.593 -9.875  73.843 3.117  -2.806 2.087  "H3'"  WSA 53 
WSA "HO3'" "HO3'" H 0 0 N N N 61.660 -8.717  72.505 5.446  -3.226 1.762  "HO3'" WSA 54 
WSA "H2'"  "H2'"  H 0 1 N N N 58.662 -11.199 72.892 3.349  -0.466 2.036  "H2'"  WSA 55 
WSA "HO2'" "HO2'" H 0 0 N N N 58.840 -9.029  71.975 5.613  -1.167 2.530  "HO2'" WSA 56 
WSA "H1'"  "H1'"  H 0 1 N N N 60.568 -11.510 70.419 4.583  -0.669 -0.769 "H1'"  WSA 57 
WSA H8     H8     H 0 1 N N N 57.976 -13.416 72.537 1.281  1.008  0.117  H8     WSA 58 
WSA H2     H2     H 0 1 N N N 59.544 -12.959 66.272 7.360  3.242  -0.548 H2     WSA 59 
WSA HN61   1HN6   H 0 0 N N N 56.060 -15.664 68.992 2.674  5.630  -0.109 HN61   WSA 60 
WSA HN62   2HN6   H 0 0 N N N 55.663 -15.058 67.528 4.130  6.450  -0.279 HN62   WSA 61 
# 
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 
WSA CD2   CE3    SING Y N 1  
WSA CD2   CE2    DOUB Y N 2  
WSA CD2   CG     SING Y N 3  
WSA CE3   CZ3    DOUB Y N 4  
WSA CE3   HE3    SING N N 5  
WSA CZ3   CH2    SING Y N 6  
WSA CZ3   HZ3    SING N N 7  
WSA CH2   CZ2    DOUB Y N 8  
WSA CH2   HH2    SING N N 9  
WSA CZ2   CE2    SING Y N 10 
WSA CZ2   HZ2    SING N N 11 
WSA CE2   N11    SING Y N 12 
WSA N11   CD1    SING Y N 13 
WSA N11   HN11   SING N N 14 
WSA CD1   CG     DOUB Y N 15 
WSA CD1   HD1    SING N N 16 
WSA CG    CB     SING N N 17 
WSA CB    CA     SING N N 18 
WSA CB    HB1    SING N N 19 
WSA CB    HB2    SING N N 20 
WSA CA    C      SING N N 21 
WSA CA    NH3    SING N N 22 
WSA CA    HA     SING N N 23 
WSA NH3   HH31   SING N N 24 
WSA NH3   HH32   SING N N 25 
WSA C     NS     SING N N 26 
WSA C     O      DOUB N N 27 
WSA NS    S      SING N N 28 
WSA NS    HNS    SING N N 29 
WSA S     "O5'"  SING N N 30 
WSA S     O2S    DOUB N N 31 
WSA S     O1S    DOUB N N 32 
WSA "O5'" "C5'"  SING N N 33 
WSA "C5'" "C4'"  SING N N 34 
WSA "C5'" "H5'1" SING N N 35 
WSA "C5'" "H5'2" SING N N 36 
WSA "C4'" "O4'"  SING N N 37 
WSA "C4'" "C3'"  SING N N 38 
WSA "C4'" "H4'"  SING N N 39 
WSA "O4'" "C1'"  SING N N 40 
WSA "C3'" "O3'"  SING N N 41 
WSA "C3'" "C2'"  SING N N 42 
WSA "C3'" "H3'"  SING N N 43 
WSA "O3'" "HO3'" SING N N 44 
WSA "C2'" "C1'"  SING N N 45 
WSA "C2'" "O2'"  SING N N 46 
WSA "C2'" "H2'"  SING N N 47 
WSA "O2'" "HO2'" SING N N 48 
WSA "C1'" N9     SING N N 49 
WSA "C1'" "H1'"  SING N N 50 
WSA N9    C4     SING Y N 51 
WSA N9    C8     SING Y N 52 
WSA C8    N7     DOUB Y N 53 
WSA C8    H8     SING N N 54 
WSA N7    C5     SING Y N 55 
WSA C5    C6     DOUB Y N 56 
WSA C5    C4     SING Y N 57 
WSA C4    N3     DOUB Y N 58 
WSA N3    C2     SING Y N 59 
WSA C2    N1     DOUB Y N 60 
WSA C2    H2     SING N N 61 
WSA N1    C6     SING Y N 62 
WSA C6    N6     SING N N 63 
WSA N6    HN61   SING N N 64 
WSA N6    HN62   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 
WSA SMILES           ACDLabs              10.04 O=C(NS(=O)(=O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O)C(N)Cc5c4ccccc4nc5 
WSA InChI            InChI                1.02b 
InChI=1/C21H24N8O7S/c22-12(5-10-6-24-13-4-2-1-3-11(10)13)20(32)28-37(33,34)35-7-14-16(30)17(31)21(36-14)29-9-27-15-18(23)25-8-26-19(15)29/h1-4,6,8-9,12,14,16-17,21,24,30-31H,5,7,22H2,(H,28,32)(H2,23,25,26)/t12-,14+,16+,17+,21+/m0/s1/f/h28H,23H2 
WSA InChIKey         InChI                1.02b RQAVKMXDGHWLGD-YJRLMDNJDZ 
WSA SMILES_CANONICAL CACTVS               3.341 N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[S](=O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45 
WSA SMILES           CACTVS               3.341 N[CH](Cc1c[nH]c2ccccc12)C(=O)N[S](=O)(=O)OC[CH]3O[CH]([CH](O)[CH]3O)n4cnc5c(N)ncnc45 
WSA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)NS(=O)(=O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4ncnc5N)O)O)N 
WSA SMILES           "OpenEye OEToolkits" 1.5.0 c1ccc2c(c1)c(c[nH]2)CC(C(=O)NS(=O)(=O)OCC3C(C(C(O3)n4cnc5c4ncnc5N)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 
WSA "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-(L-tryptophylsulfamoyl)adenosine"                                                                                      
WSA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl N-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]sulfamate" 
# 
