data_XAH
# 
_chem_comp.id                                    XAH 
_chem_comp.name                                  "5'-O-{(R)-hydroxy[(L-lysylamino)oxy]phosphoryl}adenosine" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H27 N8 O8 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-08-27 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        490.408 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XAH 
_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        3E9I 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
XAH N1   N1   N 0 1 N N N 64.203 -73.443 18.172 11.679 1.136  0.319  N1   XAH 1  
XAH C2   C2   C 0 1 N N N 63.437 -74.570 17.620 10.767 0.013  0.572  C2   XAH 2  
XAH C3   C3   C 0 1 N N N 62.355 -75.002 18.614 9.407  0.306  -0.066 C3   XAH 3  
XAH C4   C4   C 0 1 N N N 62.954 -75.559 19.908 8.457  -0.863 0.197  C4   XAH 4  
XAH C5   C5   C 0 1 N N N 61.865 -75.939 20.916 7.098  -0.570 -0.441 C5   XAH 5  
XAH C6   C6   C 0 1 N N S 61.123 -74.701 21.426 6.148  -1.740 -0.178 C6   XAH 6  
XAH N7   N7   N 0 1 N N N 62.077 -73.845 22.145 6.647  -2.940 -0.862 N7   XAH 7  
XAH C8   C8   C 0 1 N N N 59.997 -75.075 22.393 4.775  -1.399 -0.699 C8   XAH 8  
XAH O9   O9   O 0 1 N N N 59.969 -74.590 23.521 4.409  -1.832 -1.771 O9   XAH 9  
XAH N10  N10  N 0 1 N N N 59.087 -75.945 21.962 3.955  -0.613 0.027  N10  XAH 10 
XAH O11  O11  O 0 1 N N N 58.085 -76.249 22.832 2.665  -0.293 -0.463 O11  XAH 11 
XAH P12  P12  P 0 1 N N R 57.080 -77.379 22.284 1.809  0.653  0.519  P12  XAH 12 
XAH O13  O13  O 0 1 N N N 55.753 -77.085 22.869 1.609  -0.085 1.936  O13  XAH 13 
XAH O14  O14  O 0 1 N N N 57.195 -77.499 20.814 2.527  1.930  0.724  O14  XAH 14 
XAH O15  O15  O 0 1 N N N 57.665 -78.712 22.973 0.369  0.947  -0.141 O15  XAH 15 
XAH C16  C16  C 0 1 N N N 58.586 -79.558 22.279 -0.584 1.840  0.438  C16  XAH 16 
XAH C17  C17  C 0 1 N N R 58.274 -81.020 22.602 -1.837 1.887  -0.439 C17  XAH 17 
XAH O18  O18  O 0 1 N N N 58.394 -81.290 24.008 -2.499 0.612  -0.414 O18  XAH 18 
XAH C19  C19  C 0 1 N N S 56.809 -81.307 22.278 -2.827 2.928  0.118  C19  XAH 19 
XAH O20  O20  O 0 1 N N N 56.700 -81.585 20.879 -3.083 3.945  -0.854 O20  XAH 20 
XAH C21  C21  C 0 1 N N R 56.631 -82.595 23.079 -4.113 2.115  0.401  C21  XAH 21 
XAH O22  O22  O 0 1 N N N 57.269 -83.689 22.413 -5.277 2.848  0.013  O22  XAH 22 
XAH C23  C23  C 0 1 N N R 57.393 -82.262 24.365 -3.916 0.871  -0.502 C23  XAH 23 
XAH N24  N24  N 0 1 Y N N 56.542 -81.638 25.405 -4.682 -0.267 0.013  N24  XAH 24 
XAH C25  C25  C 0 1 Y N N 56.116 -80.377 25.422 -4.237 -1.204 0.897  C25  XAH 25 
XAH N26  N26  N 0 1 Y N N 55.455 -80.141 26.554 -5.177 -2.071 1.137  N26  XAH 26 
XAH C27  C27  C 0 1 Y N N 55.457 -81.264 27.266 -6.282 -1.747 0.423  C27  XAH 27 
XAH C28  C28  C 0 1 Y N N 56.145 -82.221 26.533 -5.979 -0.582 -0.302 C28  XAH 28 
XAH N29  N29  N 0 1 Y N N 56.291 -83.456 27.033 -6.911 -0.049 -1.086 N29  XAH 29 
XAH C30  C30  C 0 1 Y N N 55.789 -83.774 28.214 -8.103 -0.599 -1.182 C30  XAH 30 
XAH N31  N31  N 0 1 Y N N 55.132 -82.886 28.939 -8.435 -1.691 -0.518 N31  XAH 31 
XAH C32  C32  C 0 1 Y N N 54.946 -81.629 28.506 -7.567 -2.300 0.284  C32  XAH 32 
XAH N33  N33  N 0 1 N N N 54.301 -80.744 29.262 -7.924 -3.443 0.977  N33  XAH 33 
XAH HN1  HN1  H 0 1 N N N 64.377 -73.602 19.144 12.584 0.966  0.731  HN1  XAH 34 
XAH HN1A HN1A H 0 0 N N N 65.074 -73.362 17.687 11.760 1.320  -0.669 HN1A XAH 35 
XAH H2   H2   H 0 1 N N N 62.962 -74.260 16.677 11.182 -0.897 0.140  H2   XAH 36 
XAH H2A  H2A  H 0 1 N N N 64.117 -75.414 17.435 10.642 -0.120 1.647  H2A  XAH 37 
XAH H3   H3   H 0 1 N N N 61.736 -74.127 18.861 8.992  1.216  0.367  H3   XAH 38 
XAH H3A  H3A  H 0 1 N N N 61.758 -75.798 18.144 9.531  0.439  -1.141 H3A  XAH 39 
XAH H4   H4   H 0 1 N N N 63.543 -76.457 19.668 8.873  -1.774 -0.235 H4   XAH 40 
XAH H4A  H4A  H 0 1 N N N 63.585 -74.780 20.360 8.333  -0.996 1.272  H4A  XAH 41 
XAH H5   H5   H 0 1 N N N 61.144 -76.609 20.425 6.682  0.340  -0.008 H5   XAH 42 
XAH H5A  H5A  H 0 1 N N N 62.342 -76.437 21.773 7.222  -0.438 -1.516 H5A  XAH 43 
XAH H6   H6   H 0 1 N N N 60.685 -74.184 20.560 6.093  -1.929 0.894  H6   XAH 44 
XAH HN7  HN7  H 0 1 N N N 62.861 -73.651 21.556 6.072  -3.742 -0.651 HN7  XAH 45 
XAH HN7A HN7A H 0 0 N N N 61.630 -72.987 22.398 6.707  -2.790 -1.858 HN7A XAH 46 
XAH HN10 HN10 H 0 0 N N N 59.136 -76.353 21.050 4.248  -0.267 0.884  HN10 XAH 47 
XAH HO13 HO13 H 0 0 N N N 55.830 -77.022 23.814 1.144  -0.930 1.877  HO13 XAH 48 
XAH H16  H16  H 0 1 N N N 58.492 -79.393 21.196 -0.851 1.490  1.435  H16  XAH 49 
XAH H16A H16A H 0 0 N N N 59.613 -79.322 22.596 -0.151 2.838  0.507  H16A XAH 50 
XAH H17  H17  H 0 1 N N N 58.980 -81.630 22.018 -1.563 2.143  -1.463 H17  XAH 51 
XAH H19  H19  H 0 1 N N N 56.088 -80.508 22.505 -2.441 3.368  1.037  H19  XAH 52 
XAH HO20 HO20 H 0 0 N N N 56.676 -80.768 20.394 -3.700 4.627  -0.556 HO20 XAH 53 
XAH H21  H21  H 0 1 N N N 55.581 -82.888 23.228 -4.169 1.828  1.451  H21  XAH 54 
XAH HO22 HO22 H 0 0 N N N 57.410 -83.466 21.500 -5.393 3.681  0.489  HO22 XAH 55 
XAH H23  H23  H 0 1 N N N 57.795 -83.200 24.777 -4.203 1.094  -1.530 H23  XAH 56 
XAH H25  H25  H 0 1 N N N 56.281 -79.654 24.637 -3.250 -1.225 1.334  H25  XAH 57 
XAH H30  H30  H 0 1 N N N 55.918 -84.777 28.593 -8.837 -0.140 -1.828 H30  XAH 58 
XAH HN33 HN33 H 0 0 N N N 54.139 -81.134 30.168 -7.286 -3.872 1.568  HN33 XAH 59 
XAH HN3A HN3A H 0 0 N N N 54.854 -79.915 29.350 -8.814 -3.815 0.873  HN3A XAH 60 
# 
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 
XAH N1  C2   SING N N 1  
XAH C2  C3   SING N N 2  
XAH C3  C4   SING N N 3  
XAH C4  C5   SING N N 4  
XAH C5  C6   SING N N 5  
XAH C6  N7   SING N N 6  
XAH C6  C8   SING N N 7  
XAH C8  O9   DOUB N N 8  
XAH C8  N10  SING N N 9  
XAH N10 O11  SING N N 10 
XAH O11 P12  SING N N 11 
XAH P12 O13  SING N N 12 
XAH P12 O14  DOUB N N 13 
XAH P12 O15  SING N N 14 
XAH O15 C16  SING N N 15 
XAH C16 C17  SING N N 16 
XAH C17 O18  SING N N 17 
XAH C17 C19  SING N N 18 
XAH O18 C23  SING N N 19 
XAH C19 O20  SING N N 20 
XAH C19 C21  SING N N 21 
XAH C21 O22  SING N N 22 
XAH C21 C23  SING N N 23 
XAH C23 N24  SING N N 24 
XAH N24 C25  SING Y N 25 
XAH N24 C28  SING Y N 26 
XAH C25 N26  DOUB Y N 27 
XAH N26 C27  SING Y N 28 
XAH C27 C28  DOUB Y N 29 
XAH C27 C32  SING Y N 30 
XAH C28 N29  SING Y N 31 
XAH N29 C30  DOUB Y N 32 
XAH C30 N31  SING Y N 33 
XAH N31 C32  DOUB Y N 34 
XAH C32 N33  SING N N 35 
XAH N1  HN1  SING N N 36 
XAH N1  HN1A SING N N 37 
XAH C2  H2   SING N N 38 
XAH C2  H2A  SING N N 39 
XAH C3  H3   SING N N 40 
XAH C3  H3A  SING N N 41 
XAH C4  H4   SING N N 42 
XAH C4  H4A  SING N N 43 
XAH C5  H5   SING N N 44 
XAH C5  H5A  SING N N 45 
XAH C6  H6   SING N N 46 
XAH N7  HN7  SING N N 47 
XAH N7  HN7A SING N N 48 
XAH N10 HN10 SING N N 49 
XAH O13 HO13 SING N N 50 
XAH C16 H16  SING N N 51 
XAH C16 H16A SING N N 52 
XAH C17 H17  SING N N 53 
XAH C19 H19  SING N N 54 
XAH O20 HO20 SING N N 55 
XAH C21 H21  SING N N 56 
XAH O22 HO22 SING N N 57 
XAH C23 H23  SING N N 58 
XAH C25 H25  SING N N 59 
XAH C30 H30  SING N N 60 
XAH N33 HN33 SING N N 61 
XAH N33 HN3A SING N N 62 
# 
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 
XAH SMILES           ACDLabs              10.04 "O=P(O)(ONC(=O)C(N)CCCCN)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O" 
XAH SMILES_CANONICAL CACTVS               3.341 "NCCCC[C@H](N)C(=O)NO[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23" 
XAH SMILES           CACTVS               3.341 "NCCCC[CH](N)C(=O)NO[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23" 
XAH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@@](=O)(O)ONC(=O)[C@H](CCCCN)N)O)O)N" 
XAH SMILES           "OpenEye OEToolkits" 1.5.0 "c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)ONC(=O)C(CCCCN)N)O)O)N" 
XAH InChI            InChI                1.03  
"InChI=1S/C16H27N8O8P/c17-4-2-1-3-8(18)15(27)23-32-33(28,29)30-5-9-11(25)12(26)16(31-9)24-7-22-10-13(19)20-6-21-14(10)24/h6-9,11-12,16,25-26H,1-5,17-18H2,(H,23,27)(H,28,29)(H2,19,20,21)/t8-,9+,11+,12+,16+/m0/s1" 
XAH InChIKey         InChI                1.03  UZJSLDPAROCUBS-LEJQEAHTSA-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 
XAH "SYSTEMATIC NAME" ACDLabs              10.04 "5'-O-{(R)-hydroxy[(L-lysylamino)oxy]phosphoryl}adenosine"                                                                   
XAH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [[(2S)-2,6-diaminohexanoyl]amino] hydrogen phosphate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
XAH "Create component"     2008-08-27 PDBJ 
XAH "Modify aromatic_flag" 2011-06-04 RCSB 
XAH "Modify descriptor"    2011-06-04 RCSB 
# 
