data_XMP
# 
_chem_comp.id                                    XMP 
_chem_comp.name                                  "XANTHOSINE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C10 H14 N4 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "5-MONOPHOSPHATE-9-BETA-D-RIBOFURANOSYL XANTHINE" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     1999-07-12 
_chem_comp.pdbx_modified_date                    2026-06-15 
_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                        365.213 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XMP 
_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        1QK5 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_chem_comp.pdbx_pcm                              ? 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
XMP P      P      P 0 1 N N N N N N 26.094 44.979 61.192 5.080  0.916  0.179  P      XMP 1  
XMP OP3    O1P    O 0 1 N N N N N N 25.219 46.179 61.310 5.464  1.919  1.379  O1P    XMP 2  
XMP OP2    O2P    O 0 1 N N N N N N 27.503 45.102 60.830 6.254  -0.170 -0.009 O2P    XMP 3  
XMP "O5'"  "O5'"  O 0 1 N N N N N N 25.411 43.920 60.198 3.702  0.162  0.531  "O5'"  XMP 4  
XMP OP1    O3P    O 0 1 N N N N N N 25.957 44.296 62.525 4.916  1.686  -1.074 O3P    XMP 5  
XMP "C5'"  "C5'"  C 0 1 N N N N N N 24.030 44.158 59.982 3.041  -0.718 -0.381 "C5'"  XMP 6  
XMP "C4'"  "C4'"  C 0 1 N N R N N N 23.192 42.953 60.249 1.766  -1.261 0.267  "C4'"  XMP 7  
XMP "O4'"  "O4'"  O 0 1 N N N N N N 22.052 42.947 59.349 0.824  -0.193 0.462  "O4'"  XMP 8  
XMP "C1'"  "C1'"  C 0 1 N N R N N N 22.490 42.199 58.205 -0.493 -0.754 0.278  "C1'"  XMP 9  
XMP N9     N9     N 0 1 Y N N N N N 22.375 43.187 57.149 -1.461 0.297  -0.045 N9     XMP 10 
XMP C4     C4     C 0 1 Y N N N N N 21.623 43.108 56.018 -2.805 0.239  0.150  C4     XMP 11 
XMP N3     N3     N 0 1 N N N N N N 20.848 42.083 55.667 -3.664 -0.707 0.662  N3     XMP 12 
XMP N1     N1     N 0 1 N N N N N N 20.380 43.408 53.812 -5.532 0.682  0.309  N1     XMP 13 
XMP C2     C2     C 0 1 N N N N N N 20.210 42.244 54.501 -4.986 -0.471 0.730  C2     XMP 14 
XMP O2     O2     O 0 1 N N N N N N 19.456 41.368 54.083 -5.712 -1.332 1.188  O2     XMP 15 
XMP C6     C6     C 0 1 N N N N N N 21.187 44.492 54.152 -4.764 1.666  -0.206 C6     XMP 16 
XMP O6     O6     O 0 1 N N N N N N 21.223 45.473 53.409 -5.262 2.710  -0.587 O6     XMP 17 
XMP C5     C5     C 0 1 Y N N N N N 21.831 44.314 55.369 -3.319 1.449  -0.298 C5     XMP 18 
XMP N7     N7     N 1 1 Y N N N N N 22.714 45.112 56.087 -2.278 2.191  -0.746 N7     XMP 19 
XMP C8     C8     C 0 1 Y N N N N N 22.999 44.402 57.145 -1.176 1.514  -0.592 C8     XMP 20 
XMP "C2'"  "C2'"  C 0 1 N N R N N N 23.918 41.745 58.500 -0.311 -1.717 -0.923 "C2'"  XMP 21 
XMP "O2'"  "O2'"  O 0 1 N N N N N N 24.205 40.545 57.868 -1.295 -2.753 -0.900 "O2'"  XMP 22 
XMP "C3'"  "C3'"  C 0 1 N N S N N N 23.778 41.576 59.994 1.103  -2.292 -0.667 "C3'"  XMP 23 
XMP "O3'"  "O3'"  O 0 1 N N N N N N 22.857 40.513 60.415 1.016  -3.565 -0.024 "O3'"  XMP 24 
XMP HOP3   HOP1   H 0 0 N N N N N N 25.033 46.347 62.226 6.286  2.408  1.235  HOP1   XMP 25 
XMP HOP2   HOP2   H 0 0 N N N N N N 27.586 45.129 59.884 6.417  -0.712 0.775  HOP2   XMP 26 
XMP "H5''" "H5'2" H 0 0 N N N N N N 23.706 44.964 60.657 2.784  -0.172 -1.289 "H5'2" XMP 27 
XMP "H5'"  "H5'1" H 0 0 N N N N N N 23.898 44.430 58.924 3.704  -1.546 -0.631 "H5'1" XMP 28 
XMP "H4'"  "H4'"  H 0 1 N N N N N N 23.010 43.068 61.328 2.006  -1.724 1.224  "H4'"  XMP 29 
XMP "H1'"  "H1'"  H 0 1 N N N N N N 21.935 41.287 57.941 -0.805 -1.301 1.168  "H1'"  XMP 30 
XMP H3     H3     H 0 1 N N N N N N 20.751 41.261 56.228 -3.311 -1.554 0.976  H3     XMP 31 
XMP H1     H1     H 0 1 N N N N N N 19.863 43.494 52.960 -6.491 0.809  0.377  H1     XMP 32 
XMP H7     H7     H 0 1 N N N N N N 23.053 46.022 55.848 -2.342 3.084  -1.118 H7     XMP 33 
XMP H8     H8     H 0 1 N N N N N N 23.657 44.739 57.932 -0.189 1.862  -0.860 H8     XMP 34 
XMP "H2'"  "H2'"  H 0 1 N N N N N N 24.725 42.414 58.165 -0.345 -1.172 -1.867 "H2'"  XMP 35 
XMP "HO2'" H2O1   H 0 0 N N N N N N 24.271 40.688 56.931 -1.223 -3.381 -1.632 H2O1   XMP 36 
XMP "H3'"  "H3'"  H 0 1 N N N N N N 24.695 41.282 60.526 1.657  -2.373 -1.602 "H3'"  XMP 37 
XMP "HO3'" H3O1   H 0 0 N N N N N N 22.658 39.954 59.673 0.606  -4.253 -0.566 H3O1   XMP 38 
# 
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 
XMP P     OP3    SING N N 1  
XMP P     OP2    SING N N 2  
XMP P     "O5'"  SING N N 3  
XMP P     OP1    DOUB N N 4  
XMP OP3   HOP3   SING N N 5  
XMP OP2   HOP2   SING N N 6  
XMP "O5'" "C5'"  SING N N 7  
XMP "C5'" "C4'"  SING N N 8  
XMP "C5'" "H5''" SING N N 9  
XMP "C5'" "H5'"  SING N N 10 
XMP "C4'" "O4'"  SING N N 11 
XMP "C4'" "C3'"  SING N N 12 
XMP "C4'" "H4'"  SING N N 13 
XMP "O4'" "C1'"  SING N N 14 
XMP "C1'" N9     SING N N 15 
XMP "C1'" "C2'"  SING N N 16 
XMP "C1'" "H1'"  SING N N 17 
XMP N9    C4     SING Y N 18 
XMP N9    C8     SING Y N 19 
XMP C4    N3     SING N N 20 
XMP C4    C5     DOUB Y N 21 
XMP N3    C2     SING N N 22 
XMP N3    H3     SING N N 23 
XMP N1    C2     SING N N 24 
XMP N1    C6     SING N N 25 
XMP N1    H1     SING N N 26 
XMP C2    O2     DOUB N N 27 
XMP C6    O6     DOUB N N 28 
XMP C6    C5     SING N N 29 
XMP C5    N7     SING Y N 30 
XMP N7    C8     DOUB Y N 31 
XMP N7    H7     SING N N 32 
XMP C8    H8     SING N N 33 
XMP "C2'" "O2'"  SING N N 34 
XMP "C2'" "C3'"  SING N N 35 
XMP "C2'" "H2'"  SING N N 36 
XMP "O2'" "HO2'" SING N N 37 
XMP "C3'" "O3'"  SING N N 38 
XMP "C3'" "H3'"  SING N N 39 
XMP "O3'" "HO3'" SING N N 40 
# 
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 
XMP SMILES           ACDLabs              10.04 "O=C3Nc1c([nH+]cn1C2OC(C(O)C2O)COP(=O)(O)O)C(=O)N3"                                                                                                                      
XMP SMILES_CANONICAL CACTVS               3.341 "O[C@H]1[C@@H](O)[C@@H](O[C@@H]1CO[P](O)(O)=O)n2c[nH+]c3C(=O)NC(=O)Nc23"                                                                                                 
XMP SMILES           CACTVS               3.341 "O[CH]1[CH](O)[CH](O[CH]1CO[P](O)(O)=O)n2c[nH+]c3C(=O)NC(=O)Nc23"                                                                                                        
XMP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1[nH+]c2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)NC(=O)NC2=O"                                                                                                  
XMP SMILES           "OpenEye OEToolkits" 1.5.0 "c1[nH+]c2c(n1C3C(C(C(O3)COP(=O)(O)O)O)O)NC(=O)NC2=O"                                                                                                                    
XMP InChI            InChI                1.03  "InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/p+1/t3-,5-,6-,9-/m1/s1" 
XMP InChIKey         InChI                1.03  DCTLYFZHFGENCW-UUOKFMHZSA-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 
XMP "SYSTEMATIC NAME" ACDLabs              10.04 
;5'-xanthylic acid
;
XMP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(2,6-dioxo-3H-purin-7-ium-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen 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 
XMP "Create component"  1999-07-12 RCSB 
XMP "Modify descriptor" 2011-06-04 RCSB 
XMP "Modify synonyms"   2021-03-01 PDBE 
XMP "Modify atom id"    2026-06-15 PDBE 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      XMP 
_pdbx_chem_comp_synonyms.name         "5-MONOPHOSPHATE-9-BETA-D-RIBOFURANOSYL XANTHINE" 
_pdbx_chem_comp_synonyms.provenance   ? 
_pdbx_chem_comp_synonyms.type         ? 
# 
