data_FAD # _chem_comp.id FAD _chem_comp.name "FLAVIN-ADENINE DINUCLEOTIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H33 N9 O15 P2" _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 2011-06-04 _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 785.550 _chem_comp.one_letter_code ? _chem_comp.three_letter_code FAD _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 1B4V _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 FAD PA AP P 0 1 N N R 21.838 0.805 23.170 -1.648 -0.629 -3.229 PA FAD 1 FAD O1A AO1 O 0 1 N N N 21.303 -0.519 22.722 -3.035 -1.088 -2.992 O1A FAD 2 FAD O2A AO2 O 0 1 N N N 21.242 1.938 22.745 -0.678 -1.906 -3.378 O2A FAD 3 FAD O5B AO5* O 0 1 N N N 21.519 0.682 24.644 -1.595 0.245 -4.580 O5B FAD 4 FAD C5B AC5* C 0 1 N N N 21.897 1.643 25.685 -2.036 -0.605 -5.640 C5B FAD 5 FAD C4B AC4* C 0 1 N N R 20.997 1.330 26.945 -2.009 0.169 -6.959 C4B FAD 6 FAD O4B AO4* O 0 1 N N N 21.460 2.224 28.053 -0.665 0.583 -7.256 O4B FAD 7 FAD C3B AC3* C 0 1 N N S 19.460 1.622 26.806 -2.476 -0.741 -8.111 C3B FAD 8 FAD O3B AO3* O 0 1 N N N 18.671 0.579 27.290 -3.639 -0.203 -8.744 O3B FAD 9 FAD C2B AC2* C 0 1 N N R 19.298 2.973 27.574 -1.277 -0.748 -9.095 C2B FAD 10 FAD O2B AO2* O 0 1 N N N 18.004 3.122 28.103 -1.728 -0.672 -10.449 O2B FAD 11 FAD C1B AC1* C 0 1 N N R 20.276 2.783 28.699 -0.518 0.541 -8.692 C1B FAD 12 FAD N9A AN9 N 0 1 Y N N 20.801 4.020 29.267 0.895 0.449 -9.063 N9A FAD 13 FAD C8A AC8 C 0 1 Y N N 21.154 5.153 28.575 1.889 -0.118 -8.322 C8A FAD 14 FAD N7A AN7 N 0 1 Y N N 21.668 6.097 29.360 3.023 -0.024 -8.953 N7A FAD 15 FAD C5A AC5 C 0 1 Y N N 21.563 5.585 30.631 2.830 0.606 -10.136 C5A FAD 16 FAD C6A AC6 C 0 1 Y N N 21.927 6.147 31.932 3.663 0.979 -11.205 C6A FAD 17 FAD N6A AN6 N 0 1 N N N 22.352 7.373 32.098 5.018 0.698 -11.178 N6A FAD 18 FAD N1A AN1 N 0 1 Y N N 21.585 5.362 32.997 3.119 1.607 -12.242 N1A FAD 19 FAD C2A AC2 C 0 1 Y N N 21.028 4.127 32.847 1.827 1.878 -12.277 C2A FAD 20 FAD N3A AN3 N 0 1 Y N N 20.758 3.492 31.695 1.010 1.549 -11.299 N3A FAD 21 FAD C4A AC4 C 0 1 Y N N 21.094 4.244 30.607 1.462 0.914 -10.223 C4A FAD 22 FAD N1 N1 N 0 1 N N N 21.113 -2.231 14.334 -1.933 0.360 8.321 N1 FAD 23 FAD C2 C2 C 0 1 N N N 21.370 -3.317 13.619 -2.802 1.033 9.070 C2 FAD 24 FAD O2 O2 O 0 1 N N N 22.472 -3.795 13.558 -3.970 1.043 8.721 O2 FAD 25 FAD N3 N3 N 0 1 N N N 20.335 -4.062 12.992 -2.474 1.701 10.185 N3 FAD 26 FAD C4 C4 C 0 1 N N N 19.064 -3.545 12.870 -1.197 1.734 10.634 C4 FAD 27 FAD O4 O4 O 0 1 N N N 18.201 -4.199 12.324 -0.897 2.340 11.644 O4 FAD 28 FAD C4X C4A C 0 1 N N N 18.842 -2.220 13.431 -0.184 1.003 9.842 C4X FAD 29 FAD N5 N5 N 0 1 N N N 17.621 -1.643 13.324 1.078 0.968 10.185 N5 FAD 30 FAD C5X C5A C 0 1 Y N N 17.401 -0.507 14.054 1.969 0.295 9.446 C5X FAD 31 FAD C6 C6 C 0 1 Y N N 16.092 0.030 14.034 3.324 0.270 9.833 C6 FAD 32 FAD C7 C7 C 0 1 Y N N 15.729 1.049 14.879 4.232 -0.412 9.082 C7 FAD 33 FAD C7M C7M C 0 1 N N N 14.319 1.587 14.859 5.679 -0.434 9.502 C7M FAD 34 FAD C8 C8 C 0 1 Y N N 16.666 1.547 15.852 3.841 -1.085 7.930 C8 FAD 35 FAD C8M C8M C 0 1 N N N 16.334 2.718 16.739 4.866 -1.832 7.116 C8M FAD 36 FAD C9 C9 C 0 1 Y N N 17.942 0.981 15.928 2.523 -1.082 7.529 C9 FAD 37 FAD C9A C9A C 0 1 Y N N 18.331 0.020 14.992 1.572 -0.393 8.278 C9A FAD 38 FAD N10 N10 N 0 1 N N N 19.633 -0.566 14.994 0.253 -0.382 7.877 N10 FAD 39 FAD C10 C10 C 0 1 N N N 19.892 -1.653 14.271 -0.649 0.301 8.634 C10 FAD 40 FAD "C1'" C1* C 0 1 N N N 20.685 0.069 15.813 -0.168 -1.093 6.668 "C1'" FAD 41 FAD "C2'" C2* C 0 1 N N S 21.054 -0.797 17.045 -0.070 -0.153 5.464 "C2'" FAD 42 FAD "O2'" O2* O 0 1 N N N 19.858 -1.073 17.768 -0.919 0.977 5.673 "O2'" FAD 43 FAD "C3'" C3* C 0 1 N N S 21.986 0.046 17.903 -0.511 -0.895 4.201 "C3'" FAD 44 FAD "O3'" O3* O 0 1 N N N 23.172 0.294 17.145 0.337 -2.026 3.992 "O3'" FAD 45 FAD "C4'" C4* C 0 1 N N R 22.378 -0.732 19.167 -0.413 0.044 2.997 "C4'" FAD 46 FAD "O4'" O4* O 0 1 N N N 21.231 -1.036 19.962 -1.262 1.174 3.206 "O4'" FAD 47 FAD "C5'" C5* C 0 1 N N N 23.375 0.117 19.918 -0.854 -0.697 1.734 "C5'" FAD 48 FAD "O5'" O5* O 0 1 N N N 23.884 -0.652 21.183 -0.763 0.179 0.610 "O5'" FAD 49 FAD P P P 0 1 N N R 24.507 0.103 22.345 -1.239 -0.662 -0.677 P FAD 50 FAD O1P O1P O 0 1 N N N 24.982 -0.991 23.309 -0.354 -1.835 -0.853 O1P FAD 51 FAD O2P O2P O 0 1 N N N 25.437 1.054 21.950 -2.754 -1.160 -0.462 O2P FAD 52 FAD O3P O3P O 0 1 N N N 23.473 0.866 23.032 -1.161 0.270 -1.987 O3P FAD 53 FAD HOA2 2HOA H 0 0 N N N 21.581 2.778 23.029 0.212 -1.564 -3.531 HOA2 FAD 54 FAD H51A AH51 H 0 0 N N N 22.988 1.637 25.912 -1.374 -1.468 -5.712 H51A FAD 55 FAD H52A AH52 H 0 0 N N N 21.828 2.704 25.349 -3.052 -0.942 -5.437 H52A FAD 56 FAD H4B AH4* H 0 1 N N N 21.108 0.232 27.108 -2.659 1.041 -6.890 H4B FAD 57 FAD H3B AH3* H 0 1 N N N 19.108 1.700 25.750 -2.674 -1.748 -7.744 H3B FAD 58 FAD HO3A AHO3 H 0 0 N N N 17.741 0.755 27.205 -3.845 -0.782 -9.490 HO3A FAD 59 FAD H2B AH2* H 0 1 N N N 19.466 3.869 26.932 -0.653 -1.630 -8.944 H2B FAD 60 FAD HO2A AHO2 H 0 0 N N N 17.905 3.943 28.570 -2.190 -1.501 -10.636 HO2A FAD 61 FAD H1B AH1* H 0 1 N N N 19.760 2.196 29.494 -0.978 1.416 -9.150 H1B FAD 62 FAD H8A AH8 H 0 1 N N N 21.035 5.292 27.487 1.754 -0.577 -7.354 H8A FAD 63 FAD H61A AH61 H 0 0 N N N 22.605 7.764 33.004 5.582 0.960 -11.922 H61A FAD 64 FAD H62A AH62 H 0 0 N N N 21.653 7.992 31.686 5.403 0.239 -10.415 H62A FAD 65 FAD H2A AH2 H 0 1 N N N 20.764 3.576 33.766 1.427 2.391 -13.139 H2A FAD 66 FAD HN3 HN3 H 0 1 N N N 20.509 -4.995 12.618 -3.164 2.169 10.679 HN3 FAD 67 FAD H6 H6 H 0 1 N N N 15.330 -0.358 13.337 3.641 0.792 10.723 H6 FAD 68 FAD HM71 1HM7 H 0 0 N N N 14.024 2.414 15.545 5.853 -1.285 10.162 HM71 FAD 69 FAD HM72 2HM7 H 0 0 N N N 14.074 1.892 13.815 6.313 -0.523 8.620 HM72 FAD 70 FAD HM73 3HM7 H 0 0 N N N 13.616 0.735 15.013 5.919 0.488 10.030 HM73 FAD 71 FAD HM81 1HM8 H 0 0 N N N 17.059 3.103 17.492 5.285 -1.167 6.361 HM81 FAD 72 FAD HM82 2HM8 H 0 0 N N N 16.034 3.569 16.084 5.662 -2.185 7.772 HM82 FAD 73 FAD HM83 3HM8 H 0 0 N N N 15.380 2.487 17.268 4.393 -2.684 6.628 HM83 FAD 74 FAD H9 H9 H 0 1 N N N 18.639 1.291 16.723 2.228 -1.609 6.634 H9 FAD 75 FAD "H1'1" 1H1* H 0 0 N N N 21.585 0.310 15.201 0.478 -1.955 6.508 "H1'1" FAD 76 FAD "H1'2" 2H1* H 0 0 N N N 20.396 1.103 16.114 -1.198 -1.428 6.784 "H1'2" FAD 77 FAD "H2'" H2* H 0 1 N N N 21.540 -1.757 16.755 0.959 0.182 5.348 "H2'" FAD 78 FAD "HO2'" *HO2 H 0 0 N N N 20.084 -1.603 18.522 -1.819 0.637 5.771 "HO2'" FAD 79 FAD "H3'" H3* H 0 1 N N N 21.479 0.996 18.193 -1.541 -1.231 4.317 "H3'" FAD 80 FAD "HO3'" *HO3 H 0 0 N N N 23.753 0.820 17.680 1.237 -1.686 3.894 "HO3'" FAD 81 FAD "H4'" H4* H 0 1 N N N 22.834 -1.714 18.902 0.616 0.379 2.881 "H4'" FAD 82 FAD "HO4'" *HO4 H 0 0 N N N 21.473 -1.517 20.744 -2.162 0.834 3.304 "HO4'" FAD 83 FAD "H5'1" 1H5* H 0 0 N N N 24.215 0.451 19.265 -0.207 -1.560 1.575 "H5'1" FAD 84 FAD "H5'2" 2H5* H 0 0 N N N 22.960 1.119 20.176 -1.884 -1.033 1.850 "H5'2" FAD 85 FAD HOP2 2HOP H 0 0 N N N 25.826 1.526 22.676 -3.296 -0.367 -0.351 HOP2 FAD 86 # # 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 FAD PA O1A DOUB N N 1 FAD PA O2A SING N N 2 FAD PA O5B SING N N 3 FAD PA O3P SING N N 4 FAD O2A HOA2 SING N N 5 FAD O5B C5B SING N N 6 FAD C5B C4B SING N N 7 FAD C5B H51A SING N N 8 FAD C5B H52A SING N N 9 FAD C4B O4B SING N N 10 FAD C4B C3B SING N N 11 FAD C4B H4B SING N N 12 FAD O4B C1B SING N N 13 FAD C3B O3B SING N N 14 FAD C3B C2B SING N N 15 FAD C3B H3B SING N N 16 FAD O3B HO3A SING N N 17 FAD C2B O2B SING N N 18 FAD C2B C1B SING N N 19 FAD C2B H2B SING N N 20 FAD O2B HO2A SING N N 21 FAD C1B N9A SING N N 22 FAD C1B H1B SING N N 23 FAD N9A C8A SING Y N 24 FAD N9A C4A SING Y N 25 FAD C8A N7A DOUB Y N 26 FAD C8A H8A SING N N 27 FAD N7A C5A SING Y N 28 FAD C5A C6A SING Y N 29 FAD C5A C4A DOUB Y N 30 FAD C6A N6A SING N N 31 FAD C6A N1A DOUB Y N 32 FAD N6A H61A SING N N 33 FAD N6A H62A SING N N 34 FAD N1A C2A SING Y N 35 FAD C2A N3A DOUB Y N 36 FAD C2A H2A SING N N 37 FAD N3A C4A SING Y N 38 FAD N1 C2 SING N N 39 FAD N1 C10 DOUB N N 40 FAD C2 O2 DOUB N N 41 FAD C2 N3 SING N N 42 FAD N3 C4 SING N N 43 FAD N3 HN3 SING N N 44 FAD C4 O4 DOUB N N 45 FAD C4 C4X SING N N 46 FAD C4X N5 DOUB N N 47 FAD C4X C10 SING N N 48 FAD N5 C5X SING N N 49 FAD C5X C6 DOUB Y N 50 FAD C5X C9A SING Y N 51 FAD C6 C7 SING Y N 52 FAD C6 H6 SING N N 53 FAD C7 C7M SING N N 54 FAD C7 C8 DOUB Y N 55 FAD C7M HM71 SING N N 56 FAD C7M HM72 SING N N 57 FAD C7M HM73 SING N N 58 FAD C8 C8M SING N N 59 FAD C8 C9 SING Y N 60 FAD C8M HM81 SING N N 61 FAD C8M HM82 SING N N 62 FAD C8M HM83 SING N N 63 FAD C9 C9A DOUB Y N 64 FAD C9 H9 SING N N 65 FAD C9A N10 SING N N 66 FAD N10 C10 SING N N 67 FAD N10 "C1'" SING N N 68 FAD "C1'" "C2'" SING N N 69 FAD "C1'" "H1'1" SING N N 70 FAD "C1'" "H1'2" SING N N 71 FAD "C2'" "O2'" SING N N 72 FAD "C2'" "C3'" SING N N 73 FAD "C2'" "H2'" SING N N 74 FAD "O2'" "HO2'" SING N N 75 FAD "C3'" "O3'" SING N N 76 FAD "C3'" "C4'" SING N N 77 FAD "C3'" "H3'" SING N N 78 FAD "O3'" "HO3'" SING N N 79 FAD "C4'" "O4'" SING N N 80 FAD "C4'" "C5'" SING N N 81 FAD "C4'" "H4'" SING N N 82 FAD "O4'" "HO4'" SING N N 83 FAD "C5'" "O5'" SING N N 84 FAD "C5'" "H5'1" SING N N 85 FAD "C5'" "H5'2" SING N N 86 FAD "O5'" P SING N N 87 FAD P O1P DOUB N N 88 FAD P O2P SING N N 89 FAD P O3P SING N N 90 FAD O2P HOP2 SING N N 91 # # 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 FAD SMILES ACDLabs 10.04 "O=C2C3=Nc1cc(c(cc1N(C3=NC(=O)N2)CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC6OC(n5cnc4c(ncnc45)N)C(O)C6O)C)C" FAD SMILES_CANONICAL CACTVS 3.341 "Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6c(N)ncnc56)c2cc1C" FAD SMILES CACTVS 3.341 "Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[CH](O)[CH](O)[CH](O)CO[P](O)(=O)O[P](O)(=O)OC[CH]4O[CH]([CH](O)[CH]4O)n5cnc6c(N)ncnc56)c2cc1C" FAD 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[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)n5cnc6c5ncnc6N)O)O)O)O)O" FAD SMILES "OpenEye OEToolkits" 1.5.0 "Cc1cc2c(cc1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)n5cnc6c5ncnc6N)O)O)O)O)O" FAD InChI InChI 1.03 "InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1" FAD InChIKey InChI 1.03 VWWQXMAJTJZDQX-UYBVJOGSSA-N # # 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 FAD "SYSTEMATIC NAME" ACDLabs 10.04 "[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)" FAD "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl [[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentoxy]-hydroxy-phosphoryl] hydrogen 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 FAD "Create component" 1999-07-08 EBI FAD "Modify descriptor" 2011-06-04 RCSB ##