data_5AK
# 
_chem_comp.id                                    5AK 
_chem_comp.name                                  "8-[(2-{[2-(3-bromophenyl)ethyl]amino}-2-oxoethyl)sulfanyl]adenosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H23 Br N6 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2015-08-31 
_chem_comp.pdbx_modified_date                    2016-09-09 
_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                        539.403 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     5AK 
_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        5DHQ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
5AK C4    C1  C  0 1 Y N N 11.265 -18.084 -44.874 -5.463 -1.355 0.116  C4    5AK 1  
5AK C5    C2  C  0 1 Y N N 11.249 -17.556 -46.102 -4.636 -2.490 0.089  C5    5AK 2  
5AK C6    C3  C  0 1 Y N N 12.341 -17.553 -46.861 -5.240 -3.753 0.208  C6    5AK 3  
5AK C8    C4  C  0 1 Y N N 9.301  -17.343 -45.260 -3.349 -0.747 -0.118 C8    5AK 4  
5AK N1    N1  N  0 1 Y N N 13.508 -18.069 -46.457 -6.561 -3.814 0.339  N1    5AK 5  
5AK N3    N2  N  0 1 Y N N 12.380 -18.629 -44.365 -6.775 -1.514 0.251  N3    5AK 6  
5AK CAK   C5  C  0 1 Y N N 9.564  -19.692 -48.539 6.304  -0.684 0.130  CAK   5AK 7  
5AK CAW   C6  C  0 1 Y N N 9.829  -20.355 -47.346 7.550  -0.101 -0.016 CAW   5AK 8  
5AK BR    BR1 BR 0 0 N N N 11.548 -21.022 -47.005 8.567  0.356  1.512  BR    5AK 9  
5AK CAI   C7  C  0 1 Y N N 8.819  -20.523 -46.406 8.053  0.147  -1.281 CAI   5AK 10 
5AK CAG   C8  C  0 1 Y N N 7.545  -20.028 -46.658 7.310  -0.187 -2.398 CAG   5AK 11 
5AK CAJ   C9  C  0 1 Y N N 7.280  -19.365 -47.851 6.065  -0.769 -2.251 CAJ   5AK 12 
5AK CAY   C10 C  0 1 Y N N 8.290  -19.197 -48.792 5.564  -1.022 -0.987 CAY   5AK 13 
5AK CAN   C11 C  0 1 N N N 8.026  -18.535 -49.984 4.207  -1.657 -0.827 CAN   5AK 14 
5AK CAM   C12 C  0 1 N N N 7.248  -17.249 -49.693 3.137  -0.565 -0.766 CAM   5AK 15 
5AK NAS   N3  N  0 1 N N N 7.691  -16.689 -48.408 1.818  -1.183 -0.611 NAS   5AK 16 
5AK CAV   C13 C  0 1 N N N 6.840  -16.092 -47.563 0.717  -0.409 -0.533 CAV   5AK 17 
5AK OAB   O1  O  0 1 N N N 5.636  -15.961 -47.778 0.819  0.798  -0.591 OAB   5AK 18 
5AK CAO   C14 C  0 1 N N N 7.472  -15.567 -46.273 -0.640 -1.044 -0.373 CAO   5AK 19 
5AK SAU   S1  S  0 1 N N N 7.611  -16.931 -45.061 -1.906 0.248  -0.300 SAU   5AK 20 
5AK N7    N4  N  0 1 Y N N 10.023 -17.093 -46.343 -3.359 -2.056 -0.055 N7    5AK 21 
5AK N6    N5  N  0 1 N N N 12.210 -17.002 -48.065 -4.476 -4.908 0.187  N6    5AK 22 
5AK C2    C15 C  0 1 Y N N 13.652 -18.682 -45.119 -7.297 -2.718 0.359  C2    5AK 23 
5AK N9    N6  N  0 1 Y N N 10.048 -17.950 -44.350 -4.627 -0.269 -0.011 N9    5AK 24 
5AK "C1'" C16 C  0 1 N N R 9.613  -18.395 -43.008 -5.031 1.139  -0.030 "C1'" 5AK 25 
5AK "O4'" O2  O  0 1 N N N 8.507  -19.300 -43.138 -4.250 1.878  -0.993 "O4'" 5AK 26 
5AK "C4'" C17 C  0 1 N N R 7.914  -19.313 -41.832 -4.320 3.264  -0.615 "C4'" 5AK 27 
5AK "C5'" C18 C  0 1 N N N 6.478  -19.831 -41.928 -2.998 3.960  -0.946 "C5'" 5AK 28 
5AK "O5'" O3  O  0 1 N N N 6.451  -21.225 -41.613 -2.822 3.999  -2.364 "O5'" 5AK 29 
5AK "C3'" C19 C  0 1 N N S 7.899  -17.849 -41.421 -4.571 3.312  0.904  "C3'" 5AK 30 
5AK "O3'" O4  O  0 1 N N N 8.169  -17.743 -40.016 -5.789 4.005  1.188  "O3'" 5AK 31 
5AK "C2'" C20 C  0 1 N N R 9.047  -17.233 -42.206 -4.686 1.824  1.317  "C2'" 5AK 32 
5AK "O2'" O5  O  0 1 N N N 10.044 -16.748 -41.296 -5.737 1.638  2.267  "O2'" 5AK 33 
5AK H1    H1  H  0 1 N N N 10.349 -19.562 -49.270 5.912  -0.878 1.117  H1    5AK 34 
5AK H2    H2  H  0 1 N N N 9.024  -21.038 -45.479 9.026  0.603  -1.395 H2    5AK 35 
5AK H3    H3  H  0 1 N N N 6.761  -20.158 -45.927 7.702  0.007  -3.385 H3    5AK 36 
5AK H4    H4  H  0 1 N N N 6.290  -18.981 -48.047 5.485  -1.030 -3.123 H4    5AK 37 
5AK H5    H5  H  0 1 N N N 7.428  -19.185 -50.639 4.010  -2.311 -1.677 H5    5AK 38 
5AK H6    H6  H  0 1 N N N 8.974  -18.285 -50.482 4.185  -2.241 0.093  H6    5AK 39 
5AK H7    H7  H  0 1 N N N 7.433  -16.519 -50.495 3.335  0.089  0.084  H7    5AK 40 
5AK H8    H8  H  0 1 N N N 6.172  -17.474 -49.644 3.160  0.018  -1.686 H8    5AK 41 
5AK H9    H9  H  0 1 N N N 8.657  -16.756 -48.157 1.737  -2.148 -0.564 H9    5AK 42 
5AK H10   H10 H  0 1 N N N 8.473  -15.168 -46.492 -0.838 -1.698 -1.223 H10   5AK 43 
5AK H11   H11 H  0 1 N N N 6.842  -14.768 -45.855 -0.663 -1.627 0.547  H11   5AK 44 
5AK H12   H12 H  0 1 N N N 13.082 -17.052 -48.552 -4.904 -5.775 0.269  H12   5AK 45 
5AK H13   H13 H  0 1 N N N 11.511 -17.495 -48.583 -3.512 -4.851 0.091  H13   5AK 46 
5AK H14   H14 H  0 1 N N N 14.567 -19.113 -44.741 -8.368 -2.812 0.467  H14   5AK 47 
5AK H15   H15 H  0 1 N N N 10.448 -18.859 -42.463 -6.095 1.229  -0.245 H15   5AK 48 
5AK H16   H16 H  0 1 N N N 8.497  -19.914 -41.118 -5.140 3.751  -1.143 H16   5AK 49 
5AK H17   H17 H  0 1 N N N 5.842  -19.282 -41.217 -3.016 4.977  -0.554 H17   5AK 50 
5AK H18   H18 H  0 1 N N N 6.101  -19.679 -42.950 -2.174 3.410  -0.492 H18   5AK 51 
5AK H19   H19 H  0 1 N N N 5.559  -21.546 -41.673 -2.002 4.427  -2.646 H19   5AK 52 
5AK H20   H20 H  0 1 N N N 6.943  -17.378 -41.694 -3.735 3.788  1.415  H20   5AK 53 
5AK H21   H21 H  0 1 N N N 7.452  -18.128 -39.525 -5.793 4.927  0.896  H21   5AK 54 
5AK H22   H22 H  0 1 N N N 8.680  -16.441 -42.875 -3.739 1.455  1.710  H22   5AK 55 
5AK H23   H23 H  0 1 N N N 9.690  -16.022 -40.795 -5.568 2.049  3.126  H23   5AK 56 
# 
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 
5AK CAN   CAM   SING N N 1  
5AK CAN   CAY   SING N N 2  
5AK CAM   NAS   SING N N 3  
5AK CAY   CAK   DOUB Y N 4  
5AK CAY   CAJ   SING Y N 5  
5AK CAK   CAW   SING Y N 6  
5AK NAS   CAV   SING N N 7  
5AK N6    C6    SING N N 8  
5AK CAJ   CAG   DOUB Y N 9  
5AK OAB   CAV   DOUB N N 10 
5AK CAV   CAO   SING N N 11 
5AK CAW   BR    SING N N 12 
5AK CAW   CAI   DOUB Y N 13 
5AK C6    N1    DOUB Y N 14 
5AK C6    C5    SING Y N 15 
5AK CAG   CAI   SING Y N 16 
5AK N1    C2    SING Y N 17 
5AK N7    C5    SING Y N 18 
5AK N7    C8    DOUB Y N 19 
5AK CAO   SAU   SING N N 20 
5AK C5    C4    DOUB Y N 21 
5AK C8    SAU   SING N N 22 
5AK C8    N9    SING Y N 23 
5AK C2    N3    DOUB Y N 24 
5AK C4    N3    SING Y N 25 
5AK C4    N9    SING Y N 26 
5AK N9    "C1'" SING N N 27 
5AK "O4'" "C1'" SING N N 28 
5AK "O4'" "C4'" SING N N 29 
5AK "C1'" "C2'" SING N N 30 
5AK "C2'" "C3'" SING N N 31 
5AK "C2'" "O2'" SING N N 32 
5AK "C5'" "C4'" SING N N 33 
5AK "C5'" "O5'" SING N N 34 
5AK "C4'" "C3'" SING N N 35 
5AK "C3'" "O3'" SING N N 36 
5AK CAK   H1    SING N N 37 
5AK CAI   H2    SING N N 38 
5AK CAG   H3    SING N N 39 
5AK CAJ   H4    SING N N 40 
5AK CAN   H5    SING N N 41 
5AK CAN   H6    SING N N 42 
5AK CAM   H7    SING N N 43 
5AK CAM   H8    SING N N 44 
5AK NAS   H9    SING N N 45 
5AK CAO   H10   SING N N 46 
5AK CAO   H11   SING N N 47 
5AK N6    H12   SING N N 48 
5AK N6    H13   SING N N 49 
5AK C2    H14   SING N N 50 
5AK "C1'" H15   SING N N 51 
5AK "C4'" H16   SING N N 52 
5AK "C5'" H17   SING N N 53 
5AK "C5'" H18   SING N N 54 
5AK "O5'" H19   SING N N 55 
5AK "C3'" H20   SING N N 56 
5AK "O3'" H21   SING N N 57 
5AK "C2'" H22   SING N N 58 
5AK "O2'" H23   SING N N 59 
# 
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 
5AK SMILES           ACDLabs              12.01 "c31ncnc(c1nc(SCC(NCCc2cc(Br)ccc2)=O)n3C4C(C(C(O4)CO)O)O)N" 
5AK InChI            InChI                1.03  
"InChI=1S/C20H23BrN6O5S/c21-11-3-1-2-10(6-11)4-5-23-13(29)8-33-20-26-14-17(22)24-9-25-18(14)27(20)19-16(31)15(30)12(7-28)32-19/h1-3,6,9,12,15-16,19,28,30-31H,4-5,7-8H2,(H,23,29)(H2,22,24,25)/t12-,15-,16-,19-/m1/s1" 
5AK InChIKey         InChI                1.03  WJGLUXUMEHFNOZ-BGIGGGFGSA-N 
5AK SMILES_CANONICAL CACTVS               3.385 "Nc1ncnc2n([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c(SCC(=O)NCCc4cccc(Br)c4)nc12" 
5AK SMILES           CACTVS               3.385 "Nc1ncnc2n([CH]3O[CH](CO)[CH](O)[CH]3O)c(SCC(=O)NCCc4cccc(Br)c4)nc12" 
5AK SMILES_CANONICAL "OpenEye OEToolkits" 1.9.2 "c1cc(cc(c1)Br)CCNC(=O)CSc2nc3c(ncnc3n2[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)N" 
5AK SMILES           "OpenEye OEToolkits" 1.9.2 "c1cc(cc(c1)Br)CCNC(=O)CSc2nc3c(ncnc3n2C4C(C(C(O4)CO)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 
5AK "SYSTEMATIC NAME" ACDLabs              12.01 "8-[(2-{[2-(3-bromophenyl)ethyl]amino}-2-oxoethyl)sulfanyl]adenosine"                                                                  
5AK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.9.2 "2-[6-azanyl-9-[(2R,3R,4S,5R)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]purin-8-yl]sulfanyl-N-[2-(3-bromophenyl)ethyl]ethanamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
5AK "Create component" 2015-08-31 EBI  
5AK "Initial release"  2016-09-14 RCSB 
# 
