data_XAE
# 
_chem_comp.id                                    XAE 
_chem_comp.name                                  "3-(2-DEOXY-5-O-PHOSPHONO-BETA-D-ERYTHRO-PENTOFURANOSYL)-3H-IMIDAZO[4,5-G]QUINAZOLIN-8-AMINE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C14 H16 N5 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-09-26 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        381.281 
_chem_comp.one_letter_code                       N 
_chem_comp.three_letter_code                     XAE 
_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        2ICZ 
_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 
XAE P      P      P 0 1 N N N 12.757 4.427  6.912 3.461  4.758  -3.952 P      XAE 1  
XAE OP1    O1P    O 0 1 N N N 14.014 3.679  6.688 1.983  5.359  -4.217 OP1    XAE 2  
XAE OP2    O2P    O 0 1 N N N 12.167 4.492  8.268 4.534  5.779  -3.708 OP2    XAE 3  
XAE "C5'"  "C5'"  C 0 1 N N N 12.766 6.264  5.006 2.240  2.706  -2.896 "C5'"  XAE 4  
XAE "C4'"  "C4'"  C 0 1 N N R 12.279 7.701  4.841 2.219  1.846  -1.646 "C4'"  XAE 5  
XAE "O4'"  "O4'"  O 0 1 N N N 10.847 7.720  4.950 1.879  2.654  -0.508 "O4'"  XAE 6  
XAE "C3'"  "C3'"  C 0 1 N N S 12.770 8.666  5.914 1.177  0.741  -1.684 "C3'"  XAE 7  
XAE "C2'"  "C2'"  C 0 1 N N N 11.670 8.620  6.961 0.970  0.461  -0.212 "C2'"  XAE 8  
XAE "C1'"  "C1'"  C 0 1 N N R 10.425 8.479  6.091 1.171  1.827  0.433  "C1'"  XAE 9  
XAE "O5'"  "O5'"  O 0 1 N N N 12.966 5.934  6.384 3.235  3.702  -2.745 "O5'"  XAE 10 
XAE N9     N9     N 0 1 Y N N 9.317  7.803  6.750 -0.077 2.488  0.819  N9     XAE 11 
XAE C8     C8     C 0 1 Y N N 9.406  6.880  7.765 -0.836 3.290  0.013  C8     XAE 12 
XAE N7     N7     N 0 1 Y N N 8.227  6.447  8.141 -1.902 3.742  0.635  N7     XAE 13 
XAE C5     C5     C 0 1 Y N N 5.210  7.831  6.386 -2.377 2.676  4.194  C5     XAE 14 
XAE C4     C4     C 0 1 Y N N 5.881  8.696  5.497 -1.223 1.881  4.319  C4     XAE 15 
XAE C6     C6     C 0 1 Y N N 3.787  7.792  6.312 -3.184 2.763  5.324  C6     XAE 16 
XAE N6     N6     N 0 1 N N N 3.059  7.004  7.104 -4.366 3.544  5.278  N6     XAE 17 
XAE N1     N1     N 0 1 Y N N 3.155  8.562  5.420 -2.920 2.142  6.490  N1     XAE 18 
XAE C2     C2     C 0 1 Y N N 3.897  9.340  4.632 -1.794 1.413  6.491  C2     XAE 19 
XAE N3     N3     N 0 1 Y N N 5.230  9.483  4.586 -0.931 1.249  5.468  N3     XAE 20 
XAE C10    C10    C 0 1 Y N N 7.979  7.971  6.460 -0.695 2.418  2.041  C10    XAE 21 
XAE C11    C11    C 0 1 Y N N 7.331  7.110  7.346 -1.829 3.207  1.900  C11    XAE 22 
XAE CP     CP     C 0 1 Y N N 5.931  7.033  7.315 -2.696 3.346  2.994  CP     XAE 23 
XAE CD     CD     C 0 1 Y N N 7.275  8.767  5.534 -0.370 1.751  3.224  CD     XAE 24 
XAE "O3'"  "O3'"  O 0 1 N N N 12.753 9.978  5.341 1.636  -0.408 -2.366 "O3'"  XAE 25 
XAE OP3    O3P    O 0 1 N Y N 11.640 3.850  5.904 3.708  3.799  -5.230 OP3    XAE 26 
XAE HO1P   HO1P   H 0 0 N N N 14.126 3.519  5.758 1.875  6.082  -4.871 HO1P   XAE 27 
XAE HO3P   HO3P   H 0 0 N N N 10.820 3.736  6.370 3.963  4.205  -6.086 HO3P   XAE 28 
XAE "H5'1" "1H5'" H 0 0 N N N 12.012 5.583  4.584 1.270  3.186  -3.037 "H5'1" XAE 29 
XAE "H5'2" "2H5'" H 0 0 N N N 13.728 6.162  4.482 2.475  2.094  -3.768 "H5'2" XAE 30 
XAE "H4'"  "H4'"  H 0 1 N N N 12.670 8.025  3.865 3.224  1.436  -1.487 "H4'"  XAE 31 
XAE "H3'"  "H3'"  H 0 1 N N N 13.770 8.427  6.306 0.241  1.086  -2.140 "H3'"  XAE 32 
XAE "H2'1" "1H2'" H 0 0 N N N 11.791 7.774  7.654 -0.002 0.004  0.001  "H2'1" XAE 33 
XAE "H2'2" "2H2'" H 0 0 N N N 11.651 9.497  7.625 1.736  -0.240 0.147  "H2'2" XAE 34 
XAE "H1'"  "H1'"  H 0 1 N N N 10.038 9.477  5.839 1.753  1.756  1.357  "H1'"  XAE 35 
XAE H8     H8     H 0 1 N N N 10.337 6.550  8.201 -0.563 3.508  -1.010 H8     XAE 36 
XAE HN61   1HN6   H 0 0 N N N 2.877  6.139  6.637 -4.360 4.393  4.757  HN61   XAE 37 
XAE HN62   2HN6   H 0 0 N N N 3.561  6.827  7.950 -5.142 3.276  5.842  HN62   XAE 38 
XAE H2     H2     H 0 1 N N N 3.344  9.944  3.927 -1.550 0.900  7.413  H2     XAE 39 
XAE HP     HP     H 0 1 N N N 5.406  6.374  7.990 -3.583 3.962  2.890  HP     XAE 40 
XAE HD     HD     H 0 1 N N N 7.807  9.424  4.862 0.528  1.143  3.289  HD     XAE 41 
XAE "HO3'" H3T    H 0 0 N Y N 12.749 10.627 6.035 2.256  -0.853 -1.768 "HO3'" XAE 42 
# 
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 
XAE P     OP3    SING N N 1  
XAE P     "O5'"  SING N N 2  
XAE P     OP1    SING N N 3  
XAE P     OP2    DOUB N N 4  
XAE OP1   HO1P   SING N N 5  
XAE "C5'" "C4'"  SING N N 6  
XAE "C5'" "O5'"  SING N N 7  
XAE "C5'" "H5'1" SING N N 8  
XAE "C5'" "H5'2" SING N N 9  
XAE "C4'" "O4'"  SING N N 10 
XAE "C4'" "C3'"  SING N N 11 
XAE "C4'" "H4'"  SING N N 12 
XAE "O4'" "C1'"  SING N N 13 
XAE "C3'" "O3'"  SING N N 14 
XAE "C3'" "C2'"  SING N N 15 
XAE "C3'" "H3'"  SING N N 16 
XAE "C2'" "C1'"  SING N N 17 
XAE "C2'" "H2'1" SING N N 18 
XAE "C2'" "H2'2" SING N N 19 
XAE "C1'" N9     SING N N 20 
XAE "C1'" "H1'"  SING N N 21 
XAE N9    C10    SING Y N 22 
XAE N9    C8     SING Y N 23 
XAE C8    N7     DOUB Y N 24 
XAE C8    H8     SING N N 25 
XAE N7    C11    SING Y N 26 
XAE C5    C4     SING Y N 27 
XAE C5    C6     SING Y N 28 
XAE C5    CP     DOUB Y N 29 
XAE C4    N3     SING Y N 30 
XAE C4    CD     DOUB Y N 31 
XAE C6    N1     DOUB Y N 32 
XAE C6    N6     SING N N 33 
XAE N6    HN61   SING N N 34 
XAE N6    HN62   SING N N 35 
XAE N1    C2     SING Y N 36 
XAE C2    N3     DOUB Y N 37 
XAE C2    H2     SING N N 38 
XAE C10   CD     SING Y N 39 
XAE C10   C11    DOUB Y N 40 
XAE C11   CP     SING Y N 41 
XAE CP    HP     SING N N 42 
XAE CD    HD     SING N N 43 
XAE "O3'" "HO3'" SING N N 44 
XAE OP3   HO3P   SING N N 45 
# 
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 
XAE SMILES           ACDLabs              10.04 "O=P(O)(O)OCC4OC(n3cnc2cc1c(ncnc1cc23)N)CC4O"                                                                                                                                               
XAE InChI            InChI                1.02b "InChI=1/C14H16N5O6P/c15-14-7-1-9-10(2-8(7)16-5-17-14)19(6-18-9)13-3-11(20)12(25-13)4-24-26(21,22)23/h1-2,5-6,11-13,20H,3-4H2,(H2,15,16,17)(H2,21,22,23)/t11-,12+,13+/m0/s1/f/h21-22H,15H2" 
XAE InChIKey         InChI                1.02b UFFSWZZTZZDDDX-FPYYWALBDD                                                                                                                                                                   
XAE SMILES_CANONICAL CACTVS               3.341 "Nc1ncnc2cc3n(cnc3cc12)[C@H]4C[C@H](O)[C@@H](CO[P](O)(O)=O)O4"                                                                                                                              
XAE SMILES           CACTVS               3.341 "Nc1ncnc2cc3n(cnc3cc12)[CH]4C[CH](O)[CH](CO[P](O)(O)=O)O4"                                                                                                                                  
XAE SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1c2c(cc3c1ncn3[C@H]4C[C@@H]([C@H](O4)COP(=O)(O)O)O)ncnc2N"                                                                                                                                
XAE SMILES           "OpenEye OEToolkits" 1.5.0 "c1c2c(cc3c1ncn3C4CC(C(O4)COP(=O)(O)O)O)ncnc2N"                                                                                                                                             
# 
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 
XAE "SYSTEMATIC NAME" ACDLabs              10.04 "3-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-3H-imidazo[4,5-g]quinazolin-8-amine"               
XAE "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(8-aminopyrimido[5,6-f]benzimidazol-3-yl)-3-hydroxy-oxolan-2-yl]methyl dihydrogen phosphate" 
# 
