data_MBZ
# 
_chem_comp.id                                    MBZ 
_chem_comp.name                                  "1-[2-DEOXYRIBOFURANOSYL]-4-METHYL-BENZOIMIDAZOLE-5'-MONOPHOSPHATE" 
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H17 N2 O6 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-02-03 
_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                        328.258 
_chem_comp.one_letter_code                       N 
_chem_comp.three_letter_code                     MBZ 
_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        1EEK 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
MBZ P      P    P 0 1 N N N -0.767 -9.472  17.749 0.934  -0.167 -4.600 P      MBZ 1  
MBZ OP1    O1P  O 0 1 N N N -0.866 -10.468 18.839 1.795  0.973  -4.217 OP1    MBZ 2  
MBZ OP2    O2P  O 0 1 N N N 0.116  -9.706  16.585 1.830  -1.304 -5.304 OP2    MBZ 3  
MBZ OP3    O3P  O 0 1 N Y N -0.427 -8.041  18.370 -0.198 0.336  -5.628 OP3    MBZ 4  
MBZ "O5'"  O5*  O 0 1 N N N -2.239 -9.082  17.236 0.232  -0.774 -3.284 "O5'"  MBZ 5  
MBZ "O3'"  O3*  O 0 1 N N N -6.205 -8.123  16.047 -3.397 0.936  -1.382 "O3'"  MBZ 6  
MBZ "C1'"  C1*  C 0 1 N N R -3.952 -6.136  16.291 -0.972 -0.537 0.833  "C1'"  MBZ 7  
MBZ "C2'"  C2*  C 0 1 N N N -3.986 -7.333  15.343 -2.167 0.422  0.677  "C2'"  MBZ 8  
MBZ "C3'"  C3*  C 0 1 N N S -4.809 -8.329  16.159 -2.093 0.883  -0.798 "C3'"  MBZ 9  
MBZ "C4'"  C4*  C 0 1 N N R -4.394 -7.993  17.598 -1.241 -0.237 -1.446 "C4'"  MBZ 10 
MBZ "C5'"  C5*  C 0 1 N N N -3.319 -8.941  18.143 -0.544 0.276  -2.707 "C5'"  MBZ 11 
MBZ "O4'"  O4*  O 0 1 N N N -3.908 -6.661  17.603 -0.274 -0.563 -0.422 "O4'"  MBZ 12 
MBZ C5M    C5M  C 0 1 N N N 0.706  -1.928  16.311 2.221  0.934  5.904  C5M    MBZ 13 
MBZ C6     C6   C 0 1 Y N N -0.823 -2.273  16.313 1.097  0.194  5.227  C6     MBZ 14 
MBZ C7     C7   C 0 1 Y N N -1.261 -3.623  16.174 0.902  0.326  3.850  C7     MBZ 15 
MBZ N7     N7   N 0 1 Y N N -0.555 -4.801  15.996 1.546  1.017  2.875  N7     MBZ 16 
MBZ C8     C8   C 0 1 Y N N -1.454 -5.736  15.942 0.970  0.798  1.729  C8     MBZ 17 
MBZ N1     N1   N 0 1 Y N N -2.746 -5.299  16.093 -0.079 -0.052 1.889  N1     MBZ 18 
MBZ C9     C9   C 0 1 Y N N -2.604 -3.930  16.228 -0.146 -0.374 3.229  C9     MBZ 19 
MBZ C10    C10  C 0 1 Y N N -3.599 -2.931  16.405 -0.983 -1.179 3.989  C10    MBZ 20 
MBZ C11    C11  C 0 1 Y N N -3.195 -1.587  16.509 -0.775 -1.290 5.348  C11    MBZ 21 
MBZ C12    C12  C 0 1 Y N N -1.821 -1.260  16.447 0.263  -0.602 5.959  C12    MBZ 22 
MBZ HOP2   2HOP H 0 0 N N N 0.179  -9.066  15.885 2.232  -0.899 -6.085 HOP2   MBZ 23 
MBZ HOP3   3HOP H 0 0 N N N -0.363 -7.401  17.670 -0.735 -0.435 -5.851 HOP3   MBZ 24 
MBZ "HO'3" 3HO* H 0 0 N N N -6.716 -8.742  16.554 -3.903 1.586  -0.875 "HO'3" MBZ 25 
MBZ "H1'"  H1*  H 0 1 N N N -4.885 -5.592  16.160 -1.329 -1.536 1.080  "H1'"  MBZ 26 
MBZ "H2'"  1H2* H 0 1 N N N -3.000 -7.762  15.172 -3.104 -0.101 0.867  "H2'"  MBZ 27 
MBZ "H2''" 2H2* H 0 0 N N N -4.413 -7.066  14.377 -2.063 1.274  1.349  "H2''" MBZ 28 
MBZ "H3'"  H3*  H 0 1 N N N -4.567 -9.361  15.895 -1.593 1.848  -0.880 "H3'"  MBZ 29 
MBZ "H4'"  H4*  H 0 1 N N N -5.246 -8.045  18.279 -1.860 -1.104 -1.677 "H4'"  MBZ 30 
MBZ "H5'"  1H5* H 0 1 N N N -2.992 -8.549  19.110 -1.293 0.611  -3.426 "H5'"  MBZ 31 
MBZ "H5''" 2H5* H 0 0 N N N -3.749 -9.930  18.294 0.107  1.110  -2.448 "H5''" MBZ 32 
MBZ H71    1H5M H 0 1 N N N 0.987  -1.320  15.463 3.116  0.312  5.907  H71    MBZ 33 
MBZ H72    2H5M H 0 1 N N N 0.971  -1.379  17.219 2.424  1.859  5.365  H72    MBZ 34 
MBZ H73    3H5M H 0 1 N N N 1.369  -2.794  16.296 1.937  1.166  6.931  H73    MBZ 35 
MBZ H8     H8   H 0 1 N N N -1.174 -6.769  15.809 1.281  1.228  0.788  H8     MBZ 36 
MBZ H10    H10  H 0 1 N N N -4.664 -3.174  16.454 -1.793 -1.716 3.519  H10    MBZ 37 
MBZ H11    H11  H 0 1 N N N -3.942 -0.806  16.628 -1.425 -1.916 5.941  H11    MBZ 38 
MBZ H12    H12  H 0 1 N N N -1.530 -0.221  16.522 0.414  -0.699 7.024  H12    MBZ 39 
# 
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 
MBZ P     OP1    DOUB N N 1  
MBZ P     OP2    SING N N 2  
MBZ P     OP3    SING N N 3  
MBZ P     "O5'"  SING N N 4  
MBZ OP2   HOP2   SING N N 5  
MBZ OP3   HOP3   SING N N 6  
MBZ "O5'" "C5'"  SING N N 7  
MBZ "O3'" "C3'"  SING N N 8  
MBZ "O3'" "HO'3" SING N N 9  
MBZ "C1'" "C2'"  SING N N 10 
MBZ "C1'" "O4'"  SING N N 11 
MBZ "C1'" N1     SING N N 12 
MBZ "C1'" "H1'"  SING N N 13 
MBZ "C2'" "C3'"  SING N N 14 
MBZ "C2'" "H2'"  SING N N 15 
MBZ "C2'" "H2''" SING N N 16 
MBZ "C3'" "C4'"  SING N N 17 
MBZ "C3'" "H3'"  SING N N 18 
MBZ "C4'" "C5'"  SING N N 19 
MBZ "C4'" "O4'"  SING N N 20 
MBZ "C4'" "H4'"  SING N N 21 
MBZ "C5'" "H5'"  SING N N 22 
MBZ "C5'" "H5''" SING N N 23 
MBZ C5M   C6     SING N N 24 
MBZ C5M   H71    SING N N 25 
MBZ C5M   H72    SING N N 26 
MBZ C5M   H73    SING N N 27 
MBZ C6    C7     SING Y N 28 
MBZ C6    C12    DOUB Y N 29 
MBZ C7    N7     SING Y N 30 
MBZ C7    C9     DOUB Y N 31 
MBZ N7    C8     DOUB Y N 32 
MBZ C8    N1     SING Y N 33 
MBZ C8    H8     SING N N 34 
MBZ N1    C9     SING Y N 35 
MBZ C9    C10    SING Y N 36 
MBZ C10   C11    DOUB Y N 37 
MBZ C10   H10    SING N N 38 
MBZ C11   C12    SING Y N 39 
MBZ C11   H11    SING N N 40 
MBZ C12   H12    SING N N 41 
# 
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 
MBZ SMILES           ACDLabs              10.04 "O=P(O)(O)OCC3OC(n2cnc1c(cccc12)C)CC3O"                                                                                                                      
MBZ InChI            InChI                1.02b "InChI=1/C13H17N2O6P/c1-8-3-2-4-9-13(8)14-7-15(9)12-5-10(16)11(21-12)6-20-22(17,18)19/h2-4,7,10-12,16H,5-6H2,1H3,(H2,17,18,19)/t10-,11+,12+/m0/s1/f/h17-18H" 
MBZ InChIKey         InChI                1.02b ZNNQATJVEJKFID-DSQUKTNEDG                                                                                                                                    
MBZ SMILES_CANONICAL CACTVS               3.341 "Cc1cccc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO[P](O)(O)=O)O3"                                                                                                     
MBZ SMILES           CACTVS               3.341 "Cc1cccc2n(cnc12)[CH]3C[CH](O)[CH](CO[P](O)(O)=O)O3"                                                                                                         
MBZ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1cccc2c1ncn2[C@H]3C[C@@H]([C@H](O3)COP(=O)(O)O)O"                                                                                                         
MBZ SMILES           "OpenEye OEToolkits" 1.5.0 "Cc1cccc2c1ncn2C3CC(C(O3)COP(=O)(O)O)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 
MBZ "SYSTEMATIC NAME" ACDLabs              10.04 "1-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-4-methyl-1H-benzimidazole"          
MBZ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,5R)-3-hydroxy-5-(4-methylbenzimidazol-1-yl)oxolan-2-yl]methyl dihydrogen phosphate" 
# 
