data_SMP
# 
_chem_comp.id                                    SMP 
_chem_comp.name                                  "2'-DEOXY-ADENOSINE-5'-SP-MONOMETHYLPHOSPHONATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C11 H16 N5 O5 P" 
_chem_comp.mon_nstd_parent_comp_id               DA 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-10-09 
_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                        329.249 
_chem_comp.one_letter_code                       A 
_chem_comp.three_letter_code                     SMP 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_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 
SMP P      P    P 0 1 N N R -5.403 -6.827 6.538  1.656 -1.229 -4.986 P      SMP 1  
SMP CMP    CMP  C 0 1 N N N -6.609 -8.104 6.349  1.011 -2.866 -5.265 CMP    SMP 2  
SMP OP1    O1P  O 0 1 N N N -4.990 -6.969 7.947  2.664 -0.795 -6.011 OP1    SMP 3  
SMP "O5'"  O5*  O 0 1 N N N -5.890 -5.321 6.327  2.211 -1.232 -3.468 "O5'"  SMP 4  
SMP "C5'"  C5*  C 0 1 N N N -5.168 -4.259 6.876  1.348 -1.500 -2.377 "C5'"  SMP 5  
SMP "C4'"  C4*  C 0 1 N N R -5.763 -2.911 6.523  2.156 -1.432 -1.088 "C4'"  SMP 6  
SMP "O4'"  O4*  O 0 1 N N N -5.543 -2.629 5.165  2.678 -0.093 -0.958 "O4'"  SMP 7  
SMP "C1'"  C1*  C 0 1 N N R -6.602 -1.841 4.705  2.101 0.516  0.211  "C1'"  SMP 8  
SMP N9     N9   N 0 1 Y N N -6.707 -1.931 3.247  1.818 1.923  -0.049 N9     SMP 9  
SMP C8     C8   C 0 1 Y N N -6.960 -3.022 2.486  1.432 2.463  -1.249 C8     SMP 10 
SMP N7     N7   N 0 1 Y N N -7.133 -2.752 1.224  1.250 3.765  -1.175 N7     SMP 11 
SMP C5     C5   C 0 1 Y N N -6.951 -1.382 1.157  1.530 4.086  0.130  C5     SMP 12 
SMP C6     C6   C 0 1 Y N N -6.986 -0.454 0.094  1.519 5.292  0.822  C6     SMP 13 
SMP N6     N6   N 0 1 N N N -7.202 -0.771 -1.171 1.171 6.489  0.173  N6     SMP 14 
SMP N1     N1   N 0 1 Y N N -6.795 0.840  0.359  1.849 5.300  2.136  N1     SMP 15 
SMP C2     C2   C 0 1 Y N N -6.575 1.206  1.611  2.176 4.115  2.707  C2     SMP 16 
SMP N3     N3   N 0 1 Y N N -6.503 0.451  2.697  2.223 2.888  2.144  N3     SMP 17 
SMP C4     C4   C 0 1 Y N N -6.703 -0.861 2.397  1.886 2.954  0.847  C4     SMP 18 
SMP "C3'"  C3*  C 0 1 N N S -7.263 -2.718 6.786  1.309 -1.697 0.152  "C3'"  SMP 19 
SMP "C2'"  C2*  C 0 1 N N N -7.783 -2.489 5.382  0.878 -0.312 0.578  "C2'"  SMP 20 
SMP "O3'"  O3*  O 0 1 N N N -7.348 -1.612 7.656  2.127 -2.250 1.180  "O3'"  SMP 21 
SMP OP3    O3P  O 0 1 N Y N ?      ?      ?      0.334 -0.300 -4.927 OP3    SMP 22 
SMP HMP1   1HMP H 0 0 N N N -7.170 -7.943 5.417  1.738 -3.616 -4.945 HMP1   SMP 23 
SMP HMP2   2HMP H 0 0 N N N -7.302 -8.083 7.203  0.087 -3.006 -4.699 HMP2   SMP 24 
SMP HMP3   3HMP H 0 0 N N N -6.106 -9.081 6.310  0.799 -3.010 -6.328 HMP3   SMP 25 
SMP "H5'"  1H5* H 0 1 N N N -4.149 -4.296 6.463  0.551 -0.756 -2.359 "H5'"  SMP 26 
SMP "H5''" 2H5* H 0 0 N N N -5.170 -4.365 7.971  0.917 -2.495 -2.497 "H5''" SMP 27 
SMP "H4'"  H4*  H 0 1 N N N -5.242 -2.226 7.208  3.008 -2.117 -1.157 "H4'"  SMP 28 
SMP "H1'"  H1*  H 0 1 N N N -6.503 -0.768 4.926  2.853 0.503  1.007  "H1'"  SMP 29 
SMP H8     H8   H 0 1 N N N -7.013 -4.023 2.888  1.301 1.859  -2.137 H8     SMP 30 
SMP H61    1H6  H 0 1 N N N -6.825 -0.058 -1.762 0.205 6.745  0.096  H61    SMP 31 
SMP H62    2H6  H 0 1 N N N -8.186 -0.851 -1.332 1.883 7.025  -0.286 H62    SMP 32 
SMP H2     H2   H 0 1 N N N -6.435 2.265  1.769  2.435 4.159  3.759  H2     SMP 33 
SMP "H3'"  H3*  H 0 1 N N N -7.835 -3.526 7.266  0.475 -2.383 -0.018 "H3'"  SMP 34 
SMP "H2'"  1H2* H 0 1 N N N -8.122 -3.410 4.885  0.008 0.008  -0.009 "H2'"  SMP 35 
SMP "H2''" 2H2* H 0 0 N N N -8.670 -1.839 5.373  0.635 -0.225 1.641  "H2''" SMP 36 
SMP "HO3'" H3T  H 0 0 N Y N -8.260 -1.432 7.852  2.928 -1.706 1.218  "HO3'" SMP 37 
SMP HOP3   3HOP H 0 0 N N N 0.649  0.687  0.102  0.440 0.671  -4.846 HOP3   SMP 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 
SMP P     CMP    SING N N 1  
SMP P     OP1    DOUB N N 2  
SMP P     "O5'"  SING N N 3  
SMP P     OP3    SING N N 4  
SMP CMP   HMP1   SING N N 5  
SMP CMP   HMP2   SING N N 6  
SMP CMP   HMP3   SING N N 7  
SMP "O5'" "C5'"  SING N N 8  
SMP "C5'" "C4'"  SING N N 9  
SMP "C5'" "H5'"  SING N N 10 
SMP "C5'" "H5''" SING N N 11 
SMP "C4'" "O4'"  SING N N 12 
SMP "C4'" "C3'"  SING N N 13 
SMP "C4'" "H4'"  SING N N 14 
SMP "O4'" "C1'"  SING N N 15 
SMP "C1'" N9     SING N N 16 
SMP "C1'" "C2'"  SING N N 17 
SMP "C1'" "H1'"  SING N N 18 
SMP N9    C8     SING Y N 19 
SMP N9    C4     SING Y N 20 
SMP C8    N7     DOUB Y N 21 
SMP C8    H8     SING N N 22 
SMP N7    C5     SING Y N 23 
SMP C5    C6     DOUB Y N 24 
SMP C5    C4     SING Y N 25 
SMP C6    N6     SING N N 26 
SMP C6    N1     SING Y N 27 
SMP N6    H61    SING N N 28 
SMP N6    H62    SING N N 29 
SMP N1    C2     DOUB Y N 30 
SMP C2    N3     SING Y N 31 
SMP C2    H2     SING N N 32 
SMP N3    C4     DOUB Y N 33 
SMP "C3'" "C2'"  SING N N 34 
SMP "C3'" "O3'"  SING N N 35 
SMP "C3'" "H3'"  SING N N 36 
SMP "C2'" "H2'"  SING N N 37 
SMP "C2'" "H2''" SING N N 38 
SMP "O3'" "HO3'" SING N N 39 
SMP OP3   HOP3   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 
SMP SMILES           ACDLabs              10.04 "O=P(O)(OCC3OC(n2cnc1c(ncnc12)N)CC3O)C"                                                                                                                      
SMP InChI            InChI                1.02b "InChI=1/C11H16N5O5P/c1-22(18,19)20-3-7-6(17)2-8(21-7)16-5-15-9-10(12)13-4-14-11(9)16/h4-8,17H,2-3H2,1H3,(H,18,19)(H2,12,13,14)/t6-,7+,8+/m0/s1/f/h18H,12H2" 
SMP InChIKey         InChI                1.02b YNCYIAAXFUCITC-NDXQBBFPDN                                                                                                                                    
SMP SMILES_CANONICAL CACTVS               3.341 "C[P@](O)(=O)OC[C@H]1O[C@H](C[C@@H]1O)n2cnc3c(N)ncnc23"                                                                                                      
SMP SMILES           CACTVS               3.341 "C[P](O)(=O)OC[CH]1O[CH](C[CH]1O)n2cnc3c(N)ncnc23"                                                                                                           
SMP SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[P@@](=O)(O)OC[C@@H]1[C@H](C[C@@H](O1)n2cnc3c2ncnc3N)O"                                                                                                    
SMP SMILES           "OpenEye OEToolkits" 1.5.0 "CP(=O)(O)OCC1C(CC(O1)n2cnc3c2ncnc3N)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 
SMP "SYSTEMATIC NAME" ACDLabs              10.04 "2'-deoxy-5'-O-[(R)-hydroxy(methyl)phosphoryl]adenosine"                                 
SMP "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-oxolan-2-yl]methoxy-methyl-phosphinic acid" 
# 
