data_6CE
#

_chem_comp.id                                   6CE
_chem_comp.name                                 "5'-S-[(S)-hydroxy{[2-(1H-indol-3-yl)ethyl]amino}phosphoryl]-5'-thioguanosine"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C20 H24 N7 O6 P S"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        TrpGMPS
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2016-03-10
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       521.487
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    6CE
_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       5IPC
_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
6CE  C8   C1   C  0  1  N  N  R  -29.695  6.862  -28.436    3.475  -1.740   0.964  C8   6CE   1  
6CE  C5   C2   C  0  1  N  N  N  -29.201  4.198  -25.900    0.492  -0.364   2.283  C5   6CE   2  
6CE  C6   C3   C  0  1  N  N  S  -28.747  5.213  -26.949    1.247  -0.753   1.011  C6   6CE   3  
6CE  C2   C4   C  0  1  N  N  N  -32.184  7.803  -24.241   -5.568   1.834   0.165  C2   6CE   4  
6CE  C4   C5   C  0  1  Y  N  N  -34.079  8.592  -22.481   -7.484   0.111  -0.469  C4   6CE   5  
6CE  NE2  N1   N  0  1  N  N  N  -32.318  5.376  -23.723   -3.138   1.681   0.430  NE2  6CE   6  
6CE  P1   P1   P  0  1  N  N  N  -31.501  3.865  -23.958   -2.110   0.406   0.815  P1   6CE   7  
6CE  O2   O1   O  0  1  N  N  N  -30.294  3.802  -23.049   -2.919  -0.700   1.661  O2   6CE   8  
6CE  O3   O2   O  0  1  N  N  N  -32.524  2.767  -23.802   -1.594  -0.206  -0.430  O3   6CE   9  
6CE  S4   S1   S  0  1  N  N  N  -30.927  3.840  -25.947   -0.488   1.131   1.972  S4   6CE  10  
6CE  C7   C6   C  0  1  N  N  S  -29.490  6.547  -26.954    1.990  -2.085   1.229  C7   6CE  11  
6CE  C9   C7   C  0  1  N  N  R  -28.859  5.787  -29.110    3.362  -0.446   0.119  C9   6CE  12  
6CE  O10  O3   O  0  1  N  N  N  -28.939  4.669  -28.250    2.238   0.243   0.706  O10  6CE  13  
6CE  N11  N2   N  0  1  Y  N  N  -29.378  5.435  -30.435    4.581   0.358   0.240  N11  6CE  14  
6CE  C12  C8   C  0  1  Y  N  N  -30.664  5.225  -30.768    4.783   1.390   1.109  C12  6CE  15  
6CE  N13  N3   N  0  1  Y  N  N  -30.754  4.927  -32.087    5.981   1.873   0.940  N13  6CE  16  
6CE  C14  C9   C  0  1  Y  N  N  -29.499  4.935  -32.587    6.605   1.180  -0.041  C14  6CE  17  
6CE  C15  C10  C  0  1  Y  N  N  -28.598  5.264  -31.485    5.720   0.207  -0.489  C15  6CE  18  
6CE  N16  N4   N  0  1  N  N  N  -27.261  5.353  -31.667    6.119  -0.639  -1.492  N16  6CE  19  
6CE  C17  C11  C  0  1  N  N  N  -26.775  5.115  -32.905    7.358  -0.526  -2.039  C17  6CE  20  
6CE  N18  N5   N  0  1  N  N  N  -27.537  4.813  -33.978    8.226   0.380  -1.643  N18  6CE  21  
6CE  C19  C12  C  0  1  N  N  N  -28.868  4.699  -33.898    7.930   1.250  -0.665  C19  6CE  22  
6CE  N20  N6   N  0  1  N  N  N  -25.327  5.203  -33.090    7.717  -1.390  -3.039  N20  6CE  23  
6CE  O21  O4   O  0  1  N  N  N  -29.551  4.428  -34.919    8.744   2.087  -0.307  O21  6CE  24  
6CE  O22  O5   O  0  1  N  N  N  -28.702  7.526  -26.252    1.532  -3.070   0.300  O22  6CE  25  
6CE  O23  O6   O  0  1  N  N  N  -29.276  8.169  -28.847    4.116  -2.780   0.223  O23  6CE  26  
6CE  C1   C13  C  0  1  N  N  N  -31.589  6.613  -23.490   -4.277   1.215  -0.373  C1   6CE  27  
6CE  C3   C14  C  0  1  Y  N  N  -33.598  8.133  -23.806   -6.736   1.356  -0.659  C3   6CE  28  
6CE  C13  C15  C  0  1  Y  N  N  -34.744  8.104  -24.600   -7.288   1.990  -1.705  C13  6CE  29  
6CE  C22  C16  C  0  1  Y  N  N  -35.536  8.783  -22.621   -8.479   0.100  -1.463  C22  6CE  30  
6CE  N23  N7   N  0  1  Y  N  N  -35.851  8.476  -23.891   -8.329   1.253  -2.201  N23  6CE  31  
6CE  C24  C17  C  0  1  Y  N  N  -33.439  8.826  -21.276   -7.391  -0.949   0.435  C24  6CE  32  
6CE  C25  C18  C  0  1  Y  N  N  -34.212  9.257  -20.200   -8.264  -1.996   0.345  C25  6CE  33  
6CE  C26  C19  C  0  1  Y  N  N  -35.591  9.441  -20.315   -9.244  -2.014  -0.639  C26  6CE  34  
6CE  C27  C20  C  0  1  Y  N  N  -36.261  9.210  -21.515   -9.362  -0.972  -1.532  C27  6CE  35  
6CE  H1   H1   H  0  1  N  N  N  -30.754  6.705  -28.690    4.003  -1.549   1.899  H1   6CE  36  
6CE  H2   H2   H  0  1  N  N  N  -28.649  3.261  -26.064   -0.171  -1.178   2.576  H2   6CE  37  
6CE  H3   H3   H  0  1  N  N  N  -28.958  4.597  -24.904    1.205  -0.170   3.084  H3   6CE  38  
6CE  H4   H4   H  0  1  N  N  N  -27.678  5.416  -26.789    0.548  -0.849   0.180  H4   6CE  39  
6CE  H5   H5   H  0  1  N  N  N  -32.194  7.569  -25.316   -5.709   1.535   1.204  H5   6CE  40  
6CE  H6   H6   H  0  1  N  N  N  -31.548  8.683  -24.063   -5.502   2.921   0.106  H6   6CE  41  
6CE  H7   H7   H  0  1  N  N  N  -32.872  5.526  -24.542   -3.453   2.156   1.262  H7   6CE  42  
6CE  H8   H8   H  0  1  N  N  N  -30.361  3.041  -22.485   -3.287  -0.368   2.491  H8   6CE  43  
6CE  H9   H9   H  0  1  N  N  N  -30.470  6.420  -26.470    1.855  -2.434   2.253  H9   6CE  44  
6CE  H10  H10  H  0  1  N  N  N  -27.820  6.138  -29.196    3.162  -0.686  -0.925  H10  6CE  45  
6CE  H11  H11  H  0  1  N  N  N  -31.500  5.285  -30.086    4.061   1.751   1.826  H11  6CE  46  
6CE  H12  H12  H  0  1  N  N  N  -26.652  5.587  -30.910    5.511  -1.323  -1.815  H12  6CE  47  
6CE  H13  H13  H  0  1  N  N  N  -24.927  5.041  -33.992    7.092  -2.065  -3.344  H13  6CE  48  
6CE  H14  H14  H  0  1  N  N  N  -24.736  5.425  -32.314    8.597  -1.326  -3.441  H14  6CE  49  
6CE  H15  H15  H  0  1  N  N  N  -28.615  7.269  -25.342    2.006  -3.912   0.354  H15  6CE  50  
6CE  H16  H16  H  0  1  N  N  N  -29.811  8.824  -28.414    4.131  -3.634   0.676  H16  6CE  51  
6CE  H17  H17  H  0  1  N  N  N  -30.549  6.475  -23.819   -4.343   0.128  -0.314  H17  6CE  52  
6CE  H18  H18  H  0  1  N  N  N  -31.607  6.833  -22.412   -4.135   1.514  -1.412  H18  6CE  53  
6CE  H19  H19  H  0  1  N  N  N  -34.755  7.823  -25.643   -6.957   2.940  -2.099  H19  6CE  54  
6CE  H20  H20  H  0  1  N  N  N  -36.776  8.515  -24.268   -8.881   1.507  -2.957  H20  6CE  55  
6CE  H21  H21  H  0  1  N  N  N  -32.374  8.679  -21.173   -6.631  -0.942   1.202  H21  6CE  56  
6CE  H22  H22  H  0  1  N  N  N  -33.732  9.454  -19.253   -8.192  -2.816   1.044  H22  6CE  57  
6CE  H23  H23  H  0  1  N  N  N  -36.152  9.770  -19.453   -9.927  -2.849  -0.697  H23  6CE  58  
6CE  H24  H24  H  0  1  N  N  N  -37.328  9.361  -21.584  -10.131  -0.993  -2.290  H24  6CE  59  
#   #
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
6CE  O21  C19  DOUB  N  N   1  
6CE  N18  C19  SING  N  N   2  
6CE  N18  C17  DOUB  N  N   3  
6CE  C19  C14  SING  N  N   4  
6CE  N20  C17  SING  N  N   5  
6CE  C17  N16  SING  N  N   6  
6CE  C14  N13  SING  Y  N   7  
6CE  C14  C15  DOUB  Y  N   8  
6CE  N13  C12  DOUB  Y  N   9  
6CE  N16  C15  SING  N  N  10  
6CE  C15  N11  SING  Y  N  11  
6CE  C12  N11  SING  Y  N  12  
6CE  N11  C9   SING  N  N  13  
6CE  C9   C8   SING  N  N  14  
6CE  C9   O10  SING  N  N  15  
6CE  O23  C8   SING  N  N  16  
6CE  C8   C7   SING  N  N  17  
6CE  O10  C6   SING  N  N  18  
6CE  C7   C6   SING  N  N  19  
6CE  C7   O22  SING  N  N  20  
6CE  C6   C5   SING  N  N  21  
6CE  S4   C5   SING  N  N  22  
6CE  S4   P1   SING  N  N  23  
6CE  C13  N23  SING  Y  N  24  
6CE  C13  C3   DOUB  Y  N  25  
6CE  C2   C3   SING  N  N  26  
6CE  C2   C1   SING  N  N  27  
6CE  P1   O3   DOUB  N  N  28  
6CE  P1   NE2  SING  N  N  29  
6CE  P1   O2   SING  N  N  30  
6CE  N23  C22  SING  Y  N  31  
6CE  C3   C4   SING  Y  N  32  
6CE  NE2  C1   SING  N  N  33  
6CE  C22  C4   DOUB  Y  N  34  
6CE  C22  C27  SING  Y  N  35  
6CE  C4   C24  SING  Y  N  36  
6CE  C27  C26  DOUB  Y  N  37  
6CE  C24  C25  DOUB  Y  N  38  
6CE  C26  C25  SING  Y  N  39  
6CE  C8   H1   SING  N  N  40  
6CE  C5   H2   SING  N  N  41  
6CE  C5   H3   SING  N  N  42  
6CE  C6   H4   SING  N  N  43  
6CE  C2   H5   SING  N  N  44  
6CE  C2   H6   SING  N  N  45  
6CE  NE2  H7   SING  N  N  46  
6CE  O2   H8   SING  N  N  47  
6CE  C7   H9   SING  N  N  48  
6CE  C9   H10  SING  N  N  49  
6CE  C12  H11  SING  N  N  50  
6CE  N16  H12  SING  N  N  51  
6CE  N20  H13  SING  N  N  52  
6CE  N20  H14  SING  N  N  53  
6CE  O22  H15  SING  N  N  54  
6CE  O23  H16  SING  N  N  55  
6CE  C1   H17  SING  N  N  56  
6CE  C1   H18  SING  N  N  57  
6CE  C13  H19  SING  N  N  58  
6CE  N23  H20  SING  N  N  59  
6CE  C24  H21  SING  N  N  60  
6CE  C25  H22  SING  N  N  61  
6CE  C26  H23  SING  N  N  62  
6CE  C27  H24  SING  N  N  63  
#   #
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
6CE  SMILES            ACDLabs               12.01  "C3(C(C(CSP(NCCc2c1ccccc1nc2)(=O)O)OC3n4cnc5c4NC(=NC5=O)N)O)O"  
6CE  InChI             InChI                 1.03   "InChI=1S/C20H24N7O6PS/c21-20-25-17-14(18(30)26-20)23-9-27(17)19-16(29)15(28)13(33-19)8-35-34(31,32)24-6-5-10-7-22-12-4-2-1-3-11(10)12/h1-4,7,9,13,15-16,19,22,28-29H,5-6,8H2,(H2,24,31,32)(H3,21,25,26,30)/t13-,15-,16-,19-/m1/s1"  
6CE  InChIKey          InChI                 1.03   WJQUHDQKVRSGDO-NVQRDWNXSA-N  
6CE  SMILES_CANONICAL  CACTVS                3.385  "NC1=NC(=O)c2ncn([C@@H]3O[C@H](CS[P](O)(=O)NCCc4c[nH]c5ccccc45)[C@@H](O)[C@H]3O)c2N1"  
6CE  SMILES            CACTVS                3.385  "NC1=NC(=O)c2ncn([CH]3O[CH](CS[P](O)(=O)NCCc4c[nH]c5ccccc45)[CH](O)[CH]3O)c2N1"  
6CE  SMILES_CANONICAL  "OpenEye OEToolkits"  2.0.4  "c1ccc2c(c1)c(c[nH]2)CCNP(=O)(O)SC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4NC(=NC5=O)N)O)O"  
6CE  SMILES            "OpenEye OEToolkits"  2.0.4  "c1ccc2c(c1)c(c[nH]2)CCNP(=O)(O)SCC3C(C(C(O3)n4cnc5c4NC(=NC5=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
6CE  "SYSTEMATIC NAME"  ACDLabs               12.01  "5'-S-[(S)-hydroxy{[2-(1H-indol-3-yl)ethyl]amino}phosphoryl]-5'-thioguanosine"  
6CE  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  2.0.4  "[(2~{S},3~{S},4~{R},5~{R})-5-(2-azanyl-6-oxidanylidene-3~{H}-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methylsulfanyl-~{N}-[2-(1~{H}-indol-3-yl)ethyl]phosphonamidic acid"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
6CE  "Create component"  2016-03-10  RCSB  
6CE  "Initial release"   2017-03-15  RCSB  
6CE  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     6CE
_pdbx_chem_comp_synonyms.name        TrpGMPS
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
