data_FMN
# 
_chem_comp.id                                    FMN 
_chem_comp.name                                  "FLAVIN MONONUCLEOTIDE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H21 N4 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "RIBOFLAVIN MONOPHOSPHATE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2024-09-27 
_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                        456.344 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     FMN 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1FLM 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
_chem_comp.pdbx_pcm                              Y 
# 
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.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_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 
FMN N1     N1     N 0 1 N N N N N N 33.864 7.225  13.583 2.118  -2.493 0.531  N1     FMN 1  
FMN C2     C2     C 0 1 N N N N N N 33.031 6.319  13.062 2.713  -3.638 0.206  C2     FMN 2  
FMN O2     O2     O 0 1 N N N N N N 33.185 5.133  13.215 2.122  -4.677 0.445  O2     FMN 3  
FMN N3     N3     N 0 1 N N N N N N 31.974 6.721  12.176 3.921  -3.721 -0.368 N3     FMN 4  
FMN C4     C4     C 0 1 N N N N N N 31.788 8.007  11.826 4.636  -2.610 -0.664 C4     FMN 5  
FMN O4     O4     O 0 1 N N N N N N 30.899 8.358  11.037 5.732  -2.682 -1.185 O4     FMN 6  
FMN C4A    C4A    C 0 1 N N N N N N 32.736 8.990  12.357 4.027  -1.305 -0.325 C4A    FMN 7  
FMN N5     N5     N 0 1 N N N N N N 32.559 10.279 12.130 4.631  -0.170 -0.566 N5     FMN 8  
FMN C5A    C5A    C 0 1 Y N N N N N 33.345 11.186 12.722 4.051  0.995  -0.246 C5A    FMN 9  
FMN C6     C6     C 0 1 Y N N N N N 33.122 12.607 12.487 4.718  2.206  -0.514 C6     FMN 10 
FMN C7     C7     C 0 1 Y N N N N N 33.814 13.518 13.226 4.131  3.392  -0.190 C7     FMN 11 
FMN C7M    C7M    C 0 1 N N N N N N 33.489 15.018 13.122 4.850  4.683  -0.480 C7M    FMN 12 
FMN C8     C8     C 0 1 Y N N N N N 34.893 13.117 14.090 2.874  3.423  0.405  C8     FMN 13 
FMN C8M    C8M    C 0 1 N N N N N N 35.812 14.115 14.778 2.246  4.748  0.752  C8M    FMN 14 
FMN C9     C9     C 0 1 Y N N N N N 35.153 11.792 14.273 2.197  2.255  0.678  C9     FMN 15 
FMN C9A    C9A    C 0 1 Y N N N N N 34.382 10.809 13.674 2.774  1.029  0.359  C9A    FMN 16 
FMN N10    N10    N 0 1 N N N N N N 34.557 9.434  13.883 2.101  -0.144 0.631  N10    FMN 17 
FMN C10    C10    C 0 1 N N N N N N 33.786 8.495  13.263 2.695  -1.325 0.304  C10    FMN 18 
FMN "C1'"  "C1'"  C 0 1 N N N N N N 35.554 8.925  14.861 0.777  -0.119 1.258  "C1'"  FMN 19 
FMN "C2'"  "C2'"  C 0 1 N N S N N N 34.789 8.587  16.157 -0.300 -0.060 0.173  "C2'"  FMN 20 
FMN "O2'"  "O2'"  O 0 1 N N N N N N 34.417 9.829  16.794 -0.122 1.121  -0.611 "O2'"  FMN 21 
FMN "C3'"  "C3'"  C 0 1 N N S N N N 35.681 7.821  17.150 -1.683 -0.035 0.827  "C3'"  FMN 22 
FMN "O3'"  "O3'"  O 0 1 N N N N N N 36.849 8.662  17.488 -1.860 -1.217 1.611  "O3'"  FMN 23 
FMN "C4'"  "C4'"  C 0 1 N N R N N N 36.212 6.518  16.591 -2.760 0.024  -0.258 "C4'"  FMN 24 
FMN "O4'"  "O4'"  O 0 1 N N N N N N 35.149 5.804  15.909 -2.582 1.206  -1.042 "O4'"  FMN 25 
FMN "C5'"  "C5'"  C 0 1 N N N N N N 36.712 5.634  17.721 -4.142 0.049  0.397  "C5'"  FMN 26 
FMN "O5'"  "O5'"  O 0 1 N N N N N N 35.604 5.252  18.579 -5.149 -0.013 -0.615 "O5'"  FMN 27 
FMN P      P      P 0 1 N N N N N N 35.837 4.628  20.038 -6.725 -0.007 -0.285 P      FMN 28 
FMN O1P    O1P    O 0 1 N N N N N N 36.585 5.692  20.802 -7.053 1.180  0.536  O1P    FMN 29 
FMN O2P    O2P    O 0 1 N N N N N N 36.682 3.364  19.847 -7.561 0.045  -1.660 O2P    FMN 30 
FMN O3P    O3P    O 0 1 N N N N N N 34.436 4.306  20.554 -7.109 -1.344 0.526  O3P    FMN 31 
FMN HN3    HN3    H 0 1 N N N N N N 31.358 6.024  11.808 4.291  -4.593 -0.577 HN3    FMN 32 
FMN H6     H6     H 0 1 N N N N N N 32.417 12.933 11.737 5.695  2.195  -0.975 H6     FMN 33 
FMN HM71   HM71   H 0 0 N N N N N N 32.733 15.283 13.876 4.585  5.031  -1.479 HM71   FMN 34 
FMN HM72   HM72   H 0 0 N N N N N N 34.403 15.604 13.297 4.560  5.434  0.255  HM72   FMN 35 
FMN HM73   HM73   H 0 0 N N N N N N 33.098 15.240 12.118 5.927  4.520  -0.427 HM73   FMN 36 
FMN HM81   HM81   H 0 0 N N N N N N 35.406 14.366 15.769 1.656  5.103  -0.093 HM81   FMN 37 
FMN HM82   HM82   H 0 0 N N N N N N 36.813 13.673 14.893 1.599  4.627  1.622  HM82   FMN 38 
FMN HM83   HM83   H 0 0 N N N N N N 35.883 15.028 14.169 3.028  5.473  0.979  HM83   FMN 39 
FMN H9     H9     H 0 1 N N N N N N 35.982 11.500 14.901 1.222  2.290  1.141  H9     FMN 40 
FMN "H1'1" "H1'1" H 0 0 N N N N N N 36.043 8.023  14.466 0.642  -1.021 1.856  "H1'1" FMN 41 
FMN "H1'2" "H1'2" H 0 0 N N N N N N 36.313 9.696  15.061 0.695  0.758  1.899  "H1'2" FMN 42 
FMN "H2'"  "H2'"  H 0 1 N N N N N N 33.900 7.985  15.916 -0.218 -0.938 -0.469 "H2'"  FMN 43 
FMN "HO2'" "HO2'" H 0 0 N N N N N N 33.943 9.644  17.597 -0.183 1.942  -0.104 "HO2'" FMN 44 
FMN "H3'"  "H3'"  H 0 1 N N N N N N 35.100 7.613  18.061 -1.765 0.842  1.469  "H3'"  FMN 45 
FMN "HO3'" "HO3'" H 0 0 N N N N N N 37.407 8.198  18.101 -1.800 -2.038 1.104  "HO3'" FMN 46 
FMN "H4'"  "H4'"  H 0 1 N N N N N N 37.039 6.727  15.897 -2.677 -0.853 -0.900 "H4'"  FMN 47 
FMN "HO4'" "HO4'" H 0 0 N N N N N N 35.488 4.988  15.561 -2.642 2.027  -0.535 "HO4'" FMN 48 
FMN "H5'1" "H5'1" H 0 0 N N N N N N 37.175 4.730  17.299 -4.244 -0.807 1.064  "H5'1" FMN 49 
FMN "H5'2" "H5'2" H 0 0 N N N N N N 37.458 6.185  18.312 -4.257 0.971  0.967  "H5'2" FMN 50 
FMN HOP2   HOP2   H 0 0 N N N N N N 37.533 3.487  20.251 -8.520 0.051  -1.537 HOP2   FMN 51 
FMN HOP3   HOP3   H 0 0 N N N N N N 34.244 4.849  21.309 -6.921 -2.162 0.047  HOP3   FMN 52 
# 
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 
FMN N1    C2     SING N N 1  
FMN N1    C10    DOUB N N 2  
FMN C2    O2     DOUB N N 3  
FMN C2    N3     SING N N 4  
FMN N3    C4     SING N N 5  
FMN N3    HN3    SING N N 6  
FMN C4    O4     DOUB N N 7  
FMN C4    C4A    SING N N 8  
FMN C4A   N5     DOUB N N 9  
FMN C4A   C10    SING N N 10 
FMN N5    C5A    SING N N 11 
FMN C5A   C6     DOUB Y N 12 
FMN C5A   C9A    SING Y N 13 
FMN C6    C7     SING Y N 14 
FMN C6    H6     SING N N 15 
FMN C7    C7M    SING N N 16 
FMN C7    C8     DOUB Y N 17 
FMN C7M   HM71   SING N N 18 
FMN C7M   HM72   SING N N 19 
FMN C7M   HM73   SING N N 20 
FMN C8    C8M    SING N N 21 
FMN C8    C9     SING Y N 22 
FMN C8M   HM81   SING N N 23 
FMN C8M   HM82   SING N N 24 
FMN C8M   HM83   SING N N 25 
FMN C9    C9A    DOUB Y N 26 
FMN C9    H9     SING N N 27 
FMN C9A   N10    SING N N 28 
FMN N10   C10    SING N N 29 
FMN N10   "C1'"  SING N N 30 
FMN "C1'" "C2'"  SING N N 31 
FMN "C1'" "H1'1" SING N N 32 
FMN "C1'" "H1'2" SING N N 33 
FMN "C2'" "O2'"  SING N N 34 
FMN "C2'" "C3'"  SING N N 35 
FMN "C2'" "H2'"  SING N N 36 
FMN "O2'" "HO2'" SING N N 37 
FMN "C3'" "O3'"  SING N N 38 
FMN "C3'" "C4'"  SING N N 39 
FMN "C3'" "H3'"  SING N N 40 
FMN "O3'" "HO3'" SING N N 41 
FMN "C4'" "O4'"  SING N N 42 
FMN "C4'" "C5'"  SING N N 43 
FMN "C4'" "H4'"  SING N N 44 
FMN "O4'" "HO4'" SING N N 45 
FMN "C5'" "O5'"  SING N N 46 
FMN "C5'" "H5'1" SING N N 47 
FMN "C5'" "H5'2" SING N N 48 
FMN "O5'" P      SING N N 49 
FMN P     O1P    DOUB N N 50 
FMN P     O2P    SING N N 51 
FMN P     O3P    SING N N 52 
FMN O2P   HOP2   SING N N 53 
FMN O3P   HOP3   SING N N 54 
# 
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 
FMN SMILES           ACDLabs              12.01 "N=2C(=O)NC(=O)C3=Nc1cc(C)c(C)cc1N(C=23)CC(O)C(O)C(O)COP(=O)(O)O"                                                                                                                                
FMN InChI            InChI                1.03  "InChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1" 
FMN InChIKey         InChI                1.03  FVTCRASFADXXNN-SCRDCRAPSA-N                                                                                                                                                                      
FMN SMILES_CANONICAL CACTVS               3.385 "Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)CO[P](O)(O)=O)c2cc1C"                                                                                                                       
FMN SMILES           CACTVS               3.385 "Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[CH](O)[CH](O)[CH](O)CO[P](O)(O)=O)c2cc1C"                                                                                                                          
FMN SMILES_CANONICAL "OpenEye OEToolkits" 1.7.6 "Cc1cc2c(cc1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)O"                                                                                                                    
FMN SMILES           "OpenEye OEToolkits" 1.7.6 "Cc1cc2c(cc1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(COP(=O)(O)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 
FMN "SYSTEMATIC NAME" ACDLabs              12.01 "1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-5-O-phosphono-D-ribitol"                           
FMN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.6 "[(2R,3S,4S)-5-[7,8-dimethyl-2,4-bis(oxidanylidene)benzo[g]pteridin-10-yl]-2,3,4-tris(oxidanyl)pentyl] dihydrogen phosphate" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
FMN "Create component"     1999-07-08 RCSB 
FMN "Modify aromatic_flag" 2011-06-04 RCSB 
FMN "Modify descriptor"    2011-06-04 RCSB 
FMN "Modify aromatic_flag" 2016-02-17 RCSB 
FMN "Modify synonyms"      2020-06-05 PDBE 
FMN "Modify PCM"           2024-09-27 PDBE 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      FMN 
_pdbx_chem_comp_synonyms.name         "RIBOFLAVIN MONOPHOSPHATE" 
_pdbx_chem_comp_synonyms.provenance   ? 
_pdbx_chem_comp_synonyms.type         ? 
# 
loop_
_pdbx_chem_comp_pcm.pcm_id 
_pdbx_chem_comp_pcm.comp_id 
_pdbx_chem_comp_pcm.modified_residue_id 
_pdbx_chem_comp_pcm.type 
_pdbx_chem_comp_pcm.category 
_pdbx_chem_comp_pcm.position 
_pdbx_chem_comp_pcm.polypeptide_position 
_pdbx_chem_comp_pcm.comp_id_linking_atom 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession 
1 FMN SER None Flavin "Amino-acid side chain" "Any position" P   OG  PTM-0125 ? 
2 FMN THR None Flavin "Amino-acid side chain" "Any position" P   OG1 PTM-0126 ? 
3 FMN CYS None Flavin "Amino-acid side chain" "Any position" C4A SG  PTM-0270 ? 
4 FMN CYS None Flavin "Amino-acid side chain" "Any position" C6  SG  PTM-0271 ? 
5 FMN HIS None Flavin "Amino-acid side chain" "Any position" C8M NE2 PTM-0289 ? 
6 FMN ARG None Flavin "Amino-acid side chain" "Any position" O2P NH1 ?        ? 
7 FMN CYS None Flavin "Amino-acid side chain" "Any position" C8M SG  ?        ? 
# 
