data_DBI
# 
_chem_comp.id                                    DBI 
_chem_comp.name                                  "PHOSPHORIC ACID MONO-[5-(5,6-DIMETHYL-BENZOIMIDAZOL-1-YL)-4-HYDROXY-2-HYDROXYMETHYL-TETRAHYDRO-FURAN-3-YL] ESTER" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H19 N2 O7 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         DIMETHYLBENZIMIDAZOLE-NUCLEOTIDE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-04-11 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        358.284 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DBI 
_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        1ID8 
_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 
DBI P      P      P 0 1 N N N 0.209  -16.172 -7.452 -1.243 -0.198 -4.125 P      DBI 1  
DBI O1P    O1P    O 0 1 N N N -0.181 -17.703 -7.503 -0.306 0.693  -4.843 O1P    DBI 2  
DBI O2P    O2P    O 0 1 N N N 1.259  -15.956 -6.291 -1.762 -1.348 -5.125 O2P    DBI 3  
DBI "O3'"  "O3'"  O 0 1 N N N -1.070 -15.271 -7.182 -0.489 -0.874 -2.874 "O3'"  DBI 4  
DBI "O5'"  "O5'"  O 0 1 N N N -4.211 -17.523 -6.534 3.586  0.940  -2.731 "O5'"  DBI 5  
DBI "C5'"  "C5'"  C 0 1 N N N -4.200 -16.260 -7.150 2.176  0.926  -2.963 "C5'"  DBI 6  
DBI "C4'"  "C4'"  C 0 1 N N R -3.337 -15.257 -6.376 1.481  0.160  -1.834 "C4'"  DBI 7  
DBI "O4'"  "O4'"  O 0 1 N N N -3.894 -15.000 -5.103 1.714  0.810  -0.575 "O4'"  DBI 8  
DBI "C1'"  "C1'"  C 0 1 N N S -2.863 -14.520 -4.261 0.545  0.716  0.247  "C1'"  DBI 9  
DBI N1     N1     N 0 1 Y N N -2.860 -13.057 -4.246 0.852  -0.040 1.463  N1     DBI 10 
DBI C8     C8     C 0 1 Y N N -3.169 -12.228 -3.173 0.237  0.099  2.691  C8     DBI 11 
DBI C7     C7     C 0 1 Y N N -3.623 -12.468 -1.907 -0.778 0.910  3.176  C7     DBI 12 
DBI C6     C6     C 0 1 Y N N -3.763 -11.434 -0.974 -1.174 0.796  4.492  C6     DBI 13 
DBI C11    C11    C 0 1 N N N -4.223 -11.758 0.418  -2.277 1.676  5.022  C11    DBI 14 
DBI C10    C10    C 0 1 N N N -3.607 -8.944  -0.398 -1.000 -0.223 6.772  C10    DBI 15 
DBI C5     C5     C 0 1 Y N N -3.480 -10.114 -1.357 -0.557 -0.116 5.335  C5     DBI 16 
DBI C4     C4     C 0 1 Y N N -3.067 -9.877  -2.670 0.444  -0.924 4.874  C4     DBI 17 
DBI C9     C9     C 0 1 Y N N -2.896 -10.895 -3.567 0.858  -0.829 3.544  C9     DBI 18 
DBI N3     N3     N 0 1 Y N N -2.475 -10.938 -4.886 1.799  -1.473 2.807  N3     DBI 19 
DBI C2     C2     C 0 1 Y N N -2.465 -12.240 -5.238 1.795  -1.012 1.591  C2     DBI 20 
DBI "C2'"  "C2'"  C 0 1 N N R -1.565 -15.188 -4.747 -0.541 -0.017 -0.566 "C2'"  DBI 21 
DBI "O2'"  "O2'"  O 0 1 N N N -0.437 -14.344 -4.701 -0.576 -1.407 -0.236 "O2'"  DBI 22 
DBI "C3'"  "C3'"  C 0 1 N N S -1.904 -15.721 -6.133 -0.055 0.191  -2.028 "C3'"  DBI 23 
DBI O3P    O3P    O 0 1 N N N 0.887  -15.764 -8.828 -2.499 0.657  -3.595 O3P    DBI 24 
DBI HO2    HO2    H 0 1 N N N 1.493  -15.035 -6.260 -2.207 -0.902 -5.858 HO2    DBI 25 
DBI HO5    HO5    H 0 1 N N N -4.745 -18.144 -7.013 3.985  1.431  -3.463 HO5    DBI 26 
DBI "H5'1" "1H5'" H 0 0 N N N -5.231 -15.912 -7.227 1.969  0.436  -3.914 "H5'1" DBI 27 
DBI "H5'2" "2H5'" H 0 0 N N N -3.805 -16.397 -8.157 1.802  1.949  -2.992 "H5'2" DBI 28 
DBI "H4'"  "H4'"  H 0 1 N N N -3.335 -14.314 -6.921 1.838  -0.868 -1.801 "H4'"  DBI 29 
DBI "H1'"  "H1'"  H 0 1 N N N -3.084 -14.880 -3.252 0.198  1.715  0.511  "H1'"  DBI 30 
DBI H7     H7     H 0 1 N N N -3.900 -13.476 -1.649 -1.259 1.626  2.526  H7     DBI 31 
DBI H111   1H11   H 0 0 N N N -4.666 -12.752 0.475  -3.237 1.180  4.879  H111   DBI 32 
DBI H112   2H11   H 0 0 N N N -4.948 -11.036 0.788  -2.117 1.860  6.084  H112   DBI 33 
DBI H113   3H11   H 0 0 N N N -3.347 -11.734 1.061  -2.274 2.624  4.484  H113   DBI 34 
DBI H101   1H10   H 0 0 N N N -2.746 -8.893  0.270  -0.412 0.459  7.385  H101   DBI 35 
DBI H102   2H10   H 0 0 N N N -4.509 -8.990  0.210  -2.055 0.037  6.847  H102   DBI 36 
DBI H103   3H10   H 0 0 N N N -3.604 -7.990  -0.931 -0.852 -1.245 7.122  H103   DBI 37 
DBI H4     H4     H 0 1 N N N -2.869 -8.863  -2.965 0.915  -1.634 5.538  H4     DBI 38 
DBI H2     H2     H 0 1 N N N -2.143 -12.576 -6.212 2.447  -1.350 0.799  H2     DBI 39 
DBI "H2'"  "H2'"  H 0 1 N N N -1.337 -16.040 -4.101 -1.519 0.440  -0.413 "H2'"  DBI 40 
DBI HO21   1HO2   H 0 0 N N N -0.261 -14.087 -3.801 -0.884 -1.469 0.678  HO21   DBI 41 
DBI "H3'"  "H3'"  H 0 1 N N N -1.884 -16.810 -6.101 -0.383 1.156  -2.415 "H3'"  DBI 42 
DBI HO3    HO3    H 0 1 N N N 1.121  -14.843 -8.797 -3.084 0.040  -3.134 HO3    DBI 43 
# 
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 
DBI P     O1P    DOUB N N 1  
DBI P     O2P    SING N N 2  
DBI P     "O3'"  SING N N 3  
DBI P     O3P    SING N N 4  
DBI O2P   HO2    SING N N 5  
DBI "O3'" "C3'"  SING N N 6  
DBI "O5'" "C5'"  SING N N 7  
DBI "O5'" HO5    SING N N 8  
DBI "C5'" "C4'"  SING N N 9  
DBI "C5'" "H5'1" SING N N 10 
DBI "C5'" "H5'2" SING N N 11 
DBI "C4'" "O4'"  SING N N 12 
DBI "C4'" "C3'"  SING N N 13 
DBI "C4'" "H4'"  SING N N 14 
DBI "O4'" "C1'"  SING N N 15 
DBI "C1'" N1     SING N N 16 
DBI "C1'" "C2'"  SING N N 17 
DBI "C1'" "H1'"  SING N N 18 
DBI N1    C8     SING Y N 19 
DBI N1    C2     SING Y N 20 
DBI C8    C7     DOUB Y N 21 
DBI C8    C9     SING Y N 22 
DBI C7    C6     SING Y N 23 
DBI C7    H7     SING N N 24 
DBI C6    C11    SING N N 25 
DBI C6    C5     DOUB Y N 26 
DBI C11   H111   SING N N 27 
DBI C11   H112   SING N N 28 
DBI C11   H113   SING N N 29 
DBI C10   C5     SING N N 30 
DBI C10   H101   SING N N 31 
DBI C10   H102   SING N N 32 
DBI C10   H103   SING N N 33 
DBI C5    C4     SING Y N 34 
DBI C4    C9     DOUB Y N 35 
DBI C4    H4     SING N N 36 
DBI C9    N3     SING Y N 37 
DBI N3    C2     DOUB Y N 38 
DBI C2    H2     SING N N 39 
DBI "C2'" "O2'"  SING N N 40 
DBI "C2'" "C3'"  SING N N 41 
DBI "C2'" "H2'"  SING N N 42 
DBI "O2'" HO21   SING N N 43 
DBI "C3'" "H3'"  SING N N 44 
DBI O3P   HO3    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 
DBI SMILES           ACDLabs              10.04 O=P(O)(O)OC3C(OC(n2cnc1cc(c(cc12)C)C)C3O)CO                                                                                                                             
DBI InChI            InChI                1.02b InChI=1/C14H19N2O7P/c1-7-3-9-10(4-8(7)2)16(6-15-9)14-12(18)13(11(5-17)22-14)23-24(19,20)21/h3-4,6,11-14,17-18H,5H2,1-2H3,(H2,19,20,21)/t11-,12-,13-,14+/m1/s1/f/h19-20H 
DBI InChIKey         InChI                1.02b JIABVZWSYKDHDJ-SZZIEQPWDX                                                                                                                                               
DBI SMILES_CANONICAL CACTVS               3.341 Cc1cc2ncn([C@H]3O[C@H](CO)[C@@H](O[P](O)(O)=O)[C@H]3O)c2cc1C                                                                                                            
DBI SMILES           CACTVS               3.341 Cc1cc2ncn([CH]3O[CH](CO)[CH](O[P](O)(O)=O)[CH]3O)c2cc1C                                                                                                                 
DBI SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cc2c(cc1C)n(cn2)[C@@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)(O)O)O                                                                                                        
DBI SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cc2c(cc1C)n(cn2)C3C(C(C(O3)CO)OP(=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 
DBI "SYSTEMATIC NAME" ACDLabs              10.04 5,6-dimethyl-1-(3-O-phosphono-alpha-D-ribofuranosyl)-1H-benzimidazole                                           
DBI "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate" 
# 
