data_RBF
# 
_chem_comp.id                                    RBF 
_chem_comp.name                                  RIBOFLAVINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H20 N4 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "RIBOFLAVIN; VITAMIN B2" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        376.364 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     RBF 
_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        1BU5 
_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 
RBF N1     N1   N 0 1 Y N N 63.558 13.186 32.470 -2.385 -0.668 0.511  N1     RBF 1  
RBF C2     C2   C 0 1 Y N N 63.169 11.920 32.047 -3.567 -0.449 1.081  C2     RBF 2  
RBF O2     O2   O 0 1 N N N 62.558 11.667 31.043 -4.568 -0.723 0.444  O2     RBF 3  
RBF N3     N3   N 0 1 Y N N 63.547 10.872 32.846 -3.724 0.052  2.314  N3     RBF 4  
RBF C4     C4   C 0 1 Y N N 64.253 11.071 34.006 -2.658 0.379  3.082  C4     RBF 5  
RBF O4     O4   O 0 1 N N N 64.578 10.181 34.775 -2.798 0.835  4.200  O4     RBF 6  
RBF C4A    C4A  C 0 1 Y N N 64.656 12.448 34.429 -1.315 0.158  2.501  C4A    RBF 7  
RBF N5     N5   N 0 1 Y N N 65.305 12.580 35.525 -0.217 0.438  3.155  N5     RBF 8  
RBF C5A    C5A  C 0 1 Y N N 65.711 13.877 35.822 0.983  0.225  2.600  C5A    RBF 9  
RBF C6     C6   C 0 1 Y N N 66.487 14.059 36.962 2.153  0.533  3.320  C6     RBF 10 
RBF C7     C7   C 0 1 Y N N 66.917 15.314 37.283 3.374  0.318  2.758  C7     RBF 11 
RBF C7M    C7M  C 0 1 N N N 67.758 15.674 38.495 4.622  0.650  3.535  C7M    RBF 12 
RBF C8     C8   C 0 1 Y N N 66.550 16.417 36.470 3.483  -0.199 1.471  C8     RBF 13 
RBF C8M    C8M  C 0 1 N N N 67.052 17.822 36.915 4.847  -0.427 0.871  C8M    RBF 14 
RBF C9     C9   C 0 1 Y N N 65.798 16.295 35.350 2.357  -0.514 0.744  C9     RBF 15 
RBF C9A    C9A  C 0 1 Y N N 65.386 14.989 35.045 1.095  -0.306 1.295  C9A    RBF 16 
RBF N10    N10  N 0 1 Y N N 64.626 14.718 33.932 -0.034 -0.614 0.568  N10    RBF 17 
RBF C10    C10  C 0 1 Y N N 64.263 13.480 33.580 -1.252 -0.397 1.139  C10    RBF 18 
RBF "C1'"  C1*  C 0 1 N N N 64.153 15.809 32.997 0.071  -1.165 -0.784 "C1'"  RBF 19 
RBF "C2'"  C2*  C 0 1 N N S 62.983 16.483 33.740 0.091  -0.022 -1.800 "C2'"  RBF 20 
RBF "O2'"  O2*  O 0 1 N N N 61.799 15.638 33.723 -1.115 0.735  -1.688 "O2'"  RBF 21 
RBF "C3'"  C3*  C 0 1 N N S 62.539 17.723 33.018 0.201  -0.598 -3.213 "C3'"  RBF 22 
RBF "O3'"  O3*  O 0 1 N N N 61.857 17.222 31.904 1.408  -1.356 -3.326 "O3'"  RBF 23 
RBF "C4'"  C4*  C 0 1 N N R 63.558 18.723 32.686 0.221  0.545  -4.230 "C4'"  RBF 24 
RBF "O4'"  O4*  O 0 1 N N N 64.592 19.005 33.600 -0.984 1.303  -4.117 "O4'"  RBF 25 
RBF "C5'"  C5*  C 0 1 N N N 62.790 20.110 32.744 0.332  -0.030 -5.643 "C5'"  RBF 26 
RBF "O5'"  O5*  O 0 1 N N N 62.460 20.225 31.363 0.350  1.038  -6.592 "O5'"  RBF 27 
RBF HN3    HN3  H 0 1 N N N 63.297 9.922  32.571 -4.619 0.183  2.664  HN3    RBF 28 
RBF HC6    HC6  H 0 1 N N N 66.760 13.209 37.610 2.082  0.940  4.318  HC6    RBF 29 
RBF HC71   1HC7 H 0 0 N N N 68.109 16.699 38.757 4.934  -0.220 4.111  HC71   RBF 30 
RBF HC72   2HC7 H 0 0 N N N 67.212 15.286 39.387 5.416  0.932  2.844  HC72   RBF 31 
RBF HC73   3HC7 H 0 0 N N N 68.665 15.027 38.455 4.418  1.479  4.212  HC73   RBF 32 
RBF HC81   1HC8 H 0 0 N N N 66.763 18.689 36.276 5.162  0.468  0.336  HC81   RBF 33 
RBF HC82   2HC8 H 0 0 N N N 66.735 18.013 37.966 5.561  -0.646 1.665  HC82   RBF 34 
RBF HC83   3HC8 H 0 0 N N N 68.160 17.800 37.033 4.804  -1.268 0.179  HC83   RBF 35 
RBF HC9    HC9  H 0 1 N N N 65.544 17.179 34.741 2.452  -0.919 -0.252 HC9    RBF 36 
RBF HC11   1HC1 H 0 0 N N N 64.956 16.515 32.681 0.991  -1.744 -0.870 HC11   RBF 37 
RBF HC12   2HC1 H 0 0 N N N 63.893 15.448 31.974 -0.783 -1.812 -0.981 HC12   RBF 38 
RBF "HC2'" HC2* H 0 0 N N N 63.353 16.686 34.771 0.946  0.624  -1.603 "HC2'" RBF 39 
RBF "HO2'" HO2* H 0 0 N N N 61.077 16.053 34.181 -1.845 0.128  -1.869 "HO2'" RBF 40 
RBF "HC3'" HC3* H 0 0 N N N 61.911 18.348 33.694 -0.653 -1.244 -3.411 "HC3'" RBF 41 
RBF "HO3'" HO3* H 0 0 N N N 61.576 18.006 31.447 2.138  -0.748 -3.145 "HO3'" RBF 42 
RBF "HC4'" HC4* H 0 0 N N N 64.014 18.321 31.751 1.076  1.192  -4.033 "HC4'" RBF 43 
RBF "HO4'" HO4* H 0 0 N N N 65.252 19.653 33.384 -1.714 0.695  -4.299 "HO4'" RBF 44 
RBF HC51   1HC5 H 0 0 N N N 61.942 20.178 33.464 1.252  -0.608 -5.729 HC51   RBF 45 
RBF HC52   2HC5 H 0 0 N N N 63.343 20.966 33.195 -0.522 -0.676 -5.840 HC52   RBF 46 
RBF "HO5'" HO5* H 0 0 N N N 62.000 21.055 31.397 0.421  0.633  -7.467 "HO5'" RBF 47 
# 
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 
RBF N1    C2     SING Y N 1  
RBF N1    C10    DOUB Y N 2  
RBF C2    O2     DOUB N N 3  
RBF C2    N3     SING Y N 4  
RBF N3    C4     SING Y N 5  
RBF N3    HN3    SING N N 6  
RBF C4    O4     DOUB N N 7  
RBF C4    C4A    SING Y N 8  
RBF C4A   N5     DOUB Y N 9  
RBF C4A   C10    SING N N 10 
RBF N5    C5A    SING Y N 11 
RBF C5A   C6     DOUB Y N 12 
RBF C5A   C9A    SING Y N 13 
RBF C6    C7     SING Y N 14 
RBF C6    HC6    SING N N 15 
RBF C7    C7M    SING N N 16 
RBF C7    C8     DOUB Y N 17 
RBF C7M   HC71   SING N N 18 
RBF C7M   HC72   SING N N 19 
RBF C7M   HC73   SING N N 20 
RBF C8    C8M    SING N N 21 
RBF C8    C9     SING Y N 22 
RBF C8M   HC81   SING N N 23 
RBF C8M   HC82   SING N N 24 
RBF C8M   HC83   SING N N 25 
RBF C9    C9A    DOUB Y N 26 
RBF C9    HC9    SING N N 27 
RBF C9A   N10    SING Y N 28 
RBF N10   C10    SING Y N 29 
RBF N10   "C1'"  SING N N 30 
RBF "C1'" "C2'"  SING N N 31 
RBF "C1'" HC11   SING N N 32 
RBF "C1'" HC12   SING N N 33 
RBF "C2'" "O2'"  SING N N 34 
RBF "C2'" "C3'"  SING N N 35 
RBF "C2'" "HC2'" SING N N 36 
RBF "O2'" "HO2'" SING N N 37 
RBF "C3'" "O3'"  SING N N 38 
RBF "C3'" "C4'"  SING N N 39 
RBF "C3'" "HC3'" SING N N 40 
RBF "O3'" "HO3'" SING N N 41 
RBF "C4'" "O4'"  SING N N 42 
RBF "C4'" "C5'"  SING N N 43 
RBF "C4'" "HC4'" SING N N 44 
RBF "O4'" "HO4'" SING N N 45 
RBF "C5'" "O5'"  SING N N 46 
RBF "C5'" HC51   SING N N 47 
RBF "C5'" HC52   SING N N 48 
RBF "O5'" "HO5'" SING N N 49 
# 
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 
RBF SMILES           ACDLabs              10.04 O=C2N=C1N(c3cc(c(cc3N=C1C(=O)N2)C)C)CC(O)C(O)C(O)CO                                                                                                                        
RBF InChI            InChI                1.02b InChI=1/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1/f/h20H 
RBF InChIKey         InChI                1.02b AUNGANRZJHBGPY-QHBRKJKEDE                                                                                                                                                  
RBF SMILES_CANONICAL CACTVS               3.341 Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C                                                                                                              
RBF SMILES           CACTVS               3.341 Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[CH](O)[CH](O)[CH](O)CO)c2cc1C                                                                                                                 
RBF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 Cc1cc2c(cc1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O                                                                                                         
RBF SMILES           "OpenEye OEToolkits" 1.5.0 Cc1cc2c(cc1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)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 
RBF "SYSTEMATIC NAME" ACDLabs              10.04 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol 
RBF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione 
# 
