data_PQQ
# 
_chem_comp.id                                    PQQ 
_chem_comp.name                                  "PYRROLOQUINOLINE QUINONE" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H6 N2 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                        330.206 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PQQ 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "not provided" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   Y 
_chem_comp.pdbx_model_coordinates_db_code        1CRU 
_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 
PQQ N1   N1   N 0 1 Y N N 17.469 51.214 66.566 ? ? ? N1   PQQ 1  
PQQ C2   C2   C 0 1 Y N N 16.862 50.038 66.241 ? ? ? C2   PQQ 2  
PQQ C2X  C2X  C 0 1 N N N 17.325 49.390 65.086 ? ? ? C2X  PQQ 3  
PQQ O2A  O2A  O 0 1 N N N 18.005 50.079 64.308 ? ? ? O2A  PQQ 4  
PQQ O2B  O2B  O 0 1 N N N 17.051 48.222 64.902 ? ? ? O2B  PQQ 5  
PQQ C3   C3   C 0 1 Y N N 15.883 49.724 67.151 ? ? ? C3   PQQ 6  
PQQ C3A  C3A  C 0 1 Y N N 15.904 50.702 68.094 ? ? ? C3A  PQQ 7  
PQQ C1A  C1A  C 0 1 Y N N 16.852 51.623 67.726 ? ? ? C1A  PQQ 8  
PQQ C4   C4   C 0 1 N N N 15.201 50.846 69.274 ? ? ? C4   PQQ 9  
PQQ O4   O4   O 0 1 N N N 14.381 49.875 69.804 ? ? ? O4   PQQ 10 
PQQ C5   C5   C 0 1 N N N 15.189 52.126 70.014 ? ? ? C5   PQQ 11 
PQQ O5   O5   O 0 1 N N N 14.992 51.950 71.366 ? ? ? O5   PQQ 12 
PQQ C6A  C6A  C 0 1 Y N N 16.449 52.906 69.727 ? ? ? C6A  PQQ 13 
PQQ N6   N6   N 0 1 Y N N 16.617 53.833 70.701 ? ? ? N6   PQQ 14 
PQQ C7   C7   C 0 1 Y N N 17.530 54.752 70.466 ? ? ? C7   PQQ 15 
PQQ C7X  C7X  C 0 1 N N N 17.799 55.634 71.543 ? ? ? C7X  PQQ 16 
PQQ O7A  O7A  O 0 1 N N N 17.228 55.503 72.668 ? ? ? O7A  PQQ 17 
PQQ O7B  O7B  O 0 1 N N N 18.668 56.535 71.443 ? ? ? O7B  PQQ 18 
PQQ C8   C8   C 0 1 Y N N 18.334 54.716 69.333 ? ? ? C8   PQQ 19 
PQQ C9   C9   C 0 1 Y N N 18.144 53.720 68.346 ? ? ? C9   PQQ 20 
PQQ C9X  C9X  C 0 1 N N N 19.026 53.774 67.234 ? ? ? C9X  PQQ 21 
PQQ O9A  O9A  O 0 1 N N N 19.972 54.582 67.246 ? ? ? O9A  PQQ 22 
PQQ O9B  O9B  O 0 1 N N N 18.881 53.096 66.263 ? ? ? O9B  PQQ 23 
PQQ C9A  C9A  C 0 1 Y N N 17.194 52.749 68.544 ? ? ? C9A  PQQ 24 
PQQ HN1  HN1  H 0 1 N N N 18.217 51.682 66.055 ? ? ? HN1  PQQ 25 
PQQ HOB2 2HOB H 0 0 N N N 17.364 47.783 64.119 ? ? ? HOB2 PQQ 26 
PQQ H3   H3   H 0 1 N N N 15.208 48.851 67.128 ? ? ? H3   PQQ 27 
PQQ HOB7 7HOB H 0 0 N N N 18.848 57.126 72.164 ? ? ? HOB7 PQQ 28 
PQQ H8   H8   H 0 1 N N N 19.123 55.478 69.217 ? ? ? H8   PQQ 29 
PQQ HOB9 9HOB H 0 0 N N N 19.470 53.132 65.519 ? ? ? HOB9 PQQ 30 
# 
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 
PQQ N1  C2   SING Y N 1  
PQQ N1  C1A  SING Y N 2  
PQQ N1  HN1  SING N N 3  
PQQ C2  C2X  SING N N 4  
PQQ C2  C3   DOUB Y N 5  
PQQ C2X O2A  DOUB N N 6  
PQQ C2X O2B  SING N N 7  
PQQ O2B HOB2 SING N N 8  
PQQ C3  C3A  SING Y N 9  
PQQ C3  H3   SING N N 10 
PQQ C3A C1A  DOUB Y N 11 
PQQ C3A C4   SING N N 12 
PQQ C1A C9A  SING N N 13 
PQQ C4  O4   DOUB N N 14 
PQQ C4  C5   SING N N 15 
PQQ C5  O5   DOUB N N 16 
PQQ C5  C6A  SING N N 17 
PQQ C6A N6   DOUB Y N 18 
PQQ C6A C9A  SING Y N 19 
PQQ N6  C7   SING Y N 20 
PQQ C7  C7X  SING N N 21 
PQQ C7  C8   DOUB Y N 22 
PQQ C7X O7A  DOUB N N 23 
PQQ C7X O7B  SING N N 24 
PQQ O7B HOB7 SING N N 25 
PQQ C8  C9   SING Y N 26 
PQQ C8  H8   SING N N 27 
PQQ C9  C9X  SING N N 28 
PQQ C9  C9A  DOUB Y N 29 
PQQ C9X O9A  DOUB N N 30 
PQQ C9X O9B  SING N N 31 
PQQ O9B HOB9 SING N N 32 
# 
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 
PQQ SMILES           ACDLabs              10.04 O=C(O)c1c3c(nc(C(=O)O)c1)C(=O)C(=O)c2cc(C(=O)O)nc23                                                                                        
PQQ InChI            InChI                1.02b InChI=1/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)/f/h19,21,23H 
PQQ InChIKey         InChI                1.02b MMXZSJMASHPLLR-GYZVNBTLCJ                                                                                                                  
PQQ SMILES_CANONICAL CACTVS               3.341 OC(=O)c1[nH]c2c(c1)C(=O)C(=O)c3nc(cc(C(O)=O)c23)C(O)=O                                                                                     
PQQ SMILES           CACTVS               3.341 OC(=O)c1[nH]c2c(c1)C(=O)C(=O)c3nc(cc(C(O)=O)c23)C(O)=O                                                                                     
PQQ SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1c2c([nH]c1C(=O)O)-c3c(cc(nc3C(=O)C2=O)C(=O)O)C(=O)O                                                                                      
PQQ SMILES           "OpenEye OEToolkits" 1.5.0 c1c2c([nH]c1C(=O)O)-c3c(cc(nc3C(=O)C2=O)C(=O)O)C(=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 
PQQ "SYSTEMATIC NAME" ACDLabs              10.04 "4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid" 
PQQ "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4,5-dioxo-1H-pyrrolo[5,4-f]quinoline-2,7,9-tricarboxylic acid"             
# 
