data_DRM
# 
_chem_comp.id                                    DRM 
_chem_comp.name                                  "{[(1R,2S)-2-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)CYCLOPENTYL]OXY}METHYLPHOSPHONIC ACID" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C10 H15 N2 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               DU 
_chem_comp.pdbx_synonyms                         "1-TRANS-(2-PHOSPHONOMETHOXYCYCLOPENTYL)URACIL, PMCP-U" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-09-17 
_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                        290.210 
_chem_comp.one_letter_code                       U 
_chem_comp.three_letter_code                     DRM 
_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        1Q92 
_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 
DRM OP2    O2P  O 0 1 N N N 17.362 37.703 27.365 -2.216 -0.726 3.419  OP2    DRM 1  
DRM P      P    P 0 1 N N N 17.457 39.170 27.140 -1.369 -0.074 2.216  P      DRM 2  
DRM OP1    O1P  O 0 1 N N N 17.930 39.988 28.360 -2.106 1.084  1.665  OP1    DRM 3  
DRM OP3    O3P  O 0 1 N Y N 18.303 39.546 25.897 -1.149 -1.170 1.058  OP3    DRM 4  
DRM "C6'"  C6*  C 0 1 N N N 15.728 39.652 26.800 0.250  0.479  2.844  "C6'"  DRM 5  
DRM "O5'"  O5*  O 0 1 N N N 15.624 41.065 26.828 0.940  1.193  1.816  "O5'"  DRM 6  
DRM "C5'"  C5*  C 0 1 N N R 14.315 41.584 26.537 1.456  0.216  0.910  "C5'"  DRM 7  
DRM "C4'"  C4*  C 0 1 N N N 14.675 43.022 26.347 2.853  -0.267 1.370  "C4'"  DRM 8  
DRM "C3'"  C3*  C 0 1 N N N 14.117 43.796 27.501 3.485  -0.789 0.056  "C3'"  DRM 9  
DRM "C2'"  C2*  C 0 1 N N N 13.045 42.969 28.117 3.001  0.206  -1.017 "C2'"  DRM 10 
DRM "C1'"  C1*  C 0 1 N N R 13.316 41.521 27.726 1.707  0.845  -0.475 "C1'"  DRM 11 
DRM N1     N1   N 0 1 N N N 12.125 40.691 27.466 0.589  0.554  -1.376 N1     DRM 12 
DRM C6     C6   C 0 1 N N N 11.312 40.994 26.417 -0.110 1.584  -1.942 C6     DRM 13 
DRM C5     C5   C 0 1 N N N 10.236 40.179 26.139 -1.141 1.316  -2.772 C5     DRM 14 
DRM C4     C4   C 0 1 N N N 9.967  39.045 26.927 -1.477 -0.033 -3.039 C4     DRM 15 
DRM O4     O4   O 0 1 N N N 9.004  38.314 26.676 -2.402 -0.300 -3.785 O4     DRM 16 
DRM N3     N3   N 0 1 N N N 10.770 38.744 27.988 -0.763 -1.019 -2.461 N3     DRM 17 
DRM C2     C2   C 0 1 N N N 11.833 39.561 28.252 0.262  -0.723 -1.642 C2     DRM 18 
DRM O2     O2   O 0 1 N N N 12.583 39.358 29.234 0.898  -1.624 -1.127 O2     DRM 19 
DRM HOP2   2HOP H 0 0 N N N 17.070 37.199 26.613 -3.063 -1.005 3.045  HOP2   DRM 20 
DRM HOP3   3HOP H 0 0 N N N 18.363 40.483 25.753 -0.666 -1.906 1.458  HOP3   DRM 21 
DRM "H6'1" 1H6* H 0 0 N N N 15.347 39.218 25.845 0.839  -0.387 3.143  "H6'1" DRM 22 
DRM "H6'2" 2H6* H 0 0 N N N 15.007 39.160 27.494 0.102  1.132  3.704  "H6'2" DRM 23 
DRM "H5'"  H5*  H 0 1 N N N 13.813 41.031 25.708 0.769  -0.626 0.827  "H5'"  DRM 24 
DRM "H4'1" 1H4* H 0 0 N N N 15.770 43.177 26.213 2.763  -1.070 2.101  "H4'1" DRM 25 
DRM "H4'2" 2H4* H 0 0 N N N 14.345 43.422 25.359 3.434  0.561  1.775  "H4'2" DRM 26 
DRM "H3'1" 1H3* H 0 0 N N N 14.898 44.110 28.232 3.126  -1.794 -0.166 "H3'1" DRM 27 
DRM "H3'2" 2H3* H 0 0 N N N 13.768 44.815 27.213 4.573  -0.777 0.124  "H3'2" DRM 28 
DRM "H2'"  1H2* H 0 1 N N N 12.958 43.115 29.218 2.793  -0.319 -1.949 "H2'"  DRM 29 
DRM "H2''" 2H2* H 0 0 N N N 12.018 43.310 27.846 3.757  0.974  -1.183 "H2''" DRM 30 
DRM "H1'"  H1*  H 0 1 N N N 13.751 40.977 28.596 1.836  1.923  -0.377 "H1'"  DRM 31 
DRM H6     H6   H 0 1 N N N 11.521 41.885 25.802 0.159  2.607  -1.726 H6     DRM 32 
DRM H5     H5   H 0 1 N N N 9.588  40.435 25.283 -1.702 2.119  -3.226 H5     DRM 33 
DRM H3     H3   H 0 1 N N N 10.580 37.927 28.569 -0.987 -1.946 -2.639 H3     DRM 34 
# 
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 
DRM OP2   P      SING N N 1  
DRM OP2   HOP2   SING N N 2  
DRM P     OP1    DOUB N N 3  
DRM P     OP3    SING N N 4  
DRM P     "C6'"  SING N N 5  
DRM OP3   HOP3   SING N N 6  
DRM "C6'" "O5'"  SING N N 7  
DRM "C6'" "H6'1" SING N N 8  
DRM "C6'" "H6'2" SING N N 9  
DRM "O5'" "C5'"  SING N N 10 
DRM "C5'" "C4'"  SING N N 11 
DRM "C5'" "C1'"  SING N N 12 
DRM "C5'" "H5'"  SING N N 13 
DRM "C4'" "C3'"  SING N N 14 
DRM "C4'" "H4'1" SING N N 15 
DRM "C4'" "H4'2" SING N N 16 
DRM "C3'" "C2'"  SING N N 17 
DRM "C3'" "H3'1" SING N N 18 
DRM "C3'" "H3'2" SING N N 19 
DRM "C2'" "C1'"  SING N N 20 
DRM "C2'" "H2'"  SING N N 21 
DRM "C2'" "H2''" SING N N 22 
DRM "C1'" N1     SING N N 23 
DRM "C1'" "H1'"  SING N N 24 
DRM N1    C6     SING N N 25 
DRM N1    C2     SING N N 26 
DRM C6    C5     DOUB N N 27 
DRM C6    H6     SING N N 28 
DRM C5    C4     SING N N 29 
DRM C5    H5     SING N N 30 
DRM C4    O4     DOUB N N 31 
DRM C4    N3     SING N N 32 
DRM N3    C2     SING N N 33 
DRM N3    H3     SING N N 34 
DRM C2    O2     DOUB N N 35 
# 
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 
DRM SMILES           ACDLabs              10.04 "O=P(O)(O)COC2CCCC2N1C=CC(=O)NC1=O"                                                                                                              
DRM InChI            InChI                1.02b "InChI=1/C10H15N2O6P/c13-9-4-5-12(10(14)11-9)7-2-1-3-8(7)18-6-19(15,16)17/h4-5,7-8H,1-3,6H2,(H,11,13,14)(H2,15,16,17)/t7-,8-/m1/s1/f/h11,15-16H" 
DRM InChIKey         InChI                1.02b KKXMDNJBVSYDQL-PHIONETFDD                                                                                                                        
DRM SMILES_CANONICAL CACTVS               3.341 "O[P](O)(=O)CO[C@@H]1CCC[C@H]1N2C=CC(=O)NC2=O"                                                                                                   
DRM SMILES           CACTVS               3.341 "O[P](O)(=O)CO[CH]1CCC[CH]1N2C=CC(=O)NC2=O"                                                                                                      
DRM SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C1C[C@H]([C@@H](C1)OCP(=O)(O)O)N2C=CC(=O)NC2=O"                                                                                                 
DRM SMILES           "OpenEye OEToolkits" 1.5.0 "C1CC(C(C1)OCP(=O)(O)O)N2C=CC(=O)NC2=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 
DRM "SYSTEMATIC NAME" ACDLabs              10.04 "({[(1R,2R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)cyclopentyl]oxy}methyl)phosphonic acid" 
DRM "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1R,2R)-2-(2,4-dioxopyrimidin-1-yl)cyclopentyl]oxymethylphosphonic acid"                     
# 
