data_6FA # _chem_comp.id 6FA _chem_comp.name "6-HYDROXY-FLAVIN-ADENINE DINUCLEOTIDE" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C27 H33 N9 O16 P2" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2001-11-29 _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 801.549 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 6FA _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 1KDG _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 6FA N1 N1 N 0 1 N N N 28.487 21.198 19.773 -2.678 -1.192 -7.302 N1 6FA 1 6FA C2 C2 C 0 1 N N N 28.730 21.808 20.921 -3.952 -1.196 -7.685 C2 6FA 2 6FA O2 O2 O 0 1 N N N 28.116 21.504 21.962 -4.755 -1.799 -6.994 O2 6FA 3 6FA N3 N3 N 0 1 N N N 29.808 22.674 20.959 -4.408 -0.576 -8.783 N3 6FA 4 6FA C4 C4 C 0 1 N N N 30.329 23.297 19.864 -3.575 0.112 -9.598 C4 6FA 5 6FA O4 O4 O 0 1 N N N 31.238 24.119 19.960 -3.986 0.675 -10.594 O4 6FA 6 6FA C4A C4A C 0 1 N N N 29.932 22.727 18.565 -2.145 0.151 -9.224 C4A 6FA 7 6FA N5 N5 N 0 1 N N N 30.465 23.165 17.396 -1.254 0.790 -9.941 N5 6FA 8 6FA C5A C5A C 0 1 Y N N 30.341 22.345 16.328 0.030 0.807 -9.575 C5A 6FA 9 6FA C6 C6 C 0 1 Y N N 31.119 22.750 15.152 0.977 1.503 -10.365 C6 6FA 10 6FA O6 O6 O 0 1 N N N 31.870 23.819 15.228 0.582 2.150 -11.489 O6 6FA 11 6FA C7 C7 C 0 1 Y N N 31.092 21.856 14.002 2.302 1.524 -9.981 C7 6FA 12 6FA C7M C7M C 0 1 N N N 31.924 22.186 12.794 3.311 2.265 -10.820 C7M 6FA 13 6FA C8 C8 C 0 1 Y N N 30.378 20.598 14.133 2.714 0.859 -8.836 C8 6FA 14 6FA C8M C8M C 0 1 N N N 30.327 19.706 12.906 4.168 0.889 -8.439 C8M 6FA 15 6FA C9 C9 C 0 1 Y N N 29.569 20.395 15.250 1.808 0.175 -8.053 C9 6FA 16 6FA C9A C9A C 0 1 Y N N 29.648 21.206 16.358 0.465 0.139 -8.407 C9A 6FA 17 6FA N10 N10 N 0 1 N N N 28.774 20.987 17.447 -0.439 -0.546 -7.621 N10 6FA 18 6FA C10 C10 C 0 1 N N N 29.089 21.651 18.622 -1.748 -0.560 -7.999 C10 6FA 19 6FA "C1'" C1* C 0 1 N N N 27.866 19.880 17.448 -0.001 -1.241 -6.409 "C1'" 6FA 20 6FA "C2'" C2* C 0 1 N N S 28.323 18.543 18.014 -0.085 -0.287 -5.215 "C2'" 6FA 21 6FA "O2'" O2* O 0 1 N N N 29.679 18.309 17.669 0.759 0.841 -5.448 "O2'" 6FA 22 6FA "C3'" C3* C 0 1 N N S 27.416 17.469 17.422 0.371 -1.014 -3.949 "C3'" 6FA 23 6FA "O3'" O3* O 0 1 N N N 26.066 17.709 17.754 -0.473 -2.143 -3.716 "O3'" 6FA 24 6FA "C4'" C4* C 0 1 N N R 27.746 16.068 17.865 0.287 -0.060 -2.755 "C4'" 6FA 25 6FA "O4'" O4* O 0 1 N N N 29.098 15.722 17.525 1.132 1.068 -2.988 "O4'" 6FA 26 6FA "C5'" C5* C 0 1 N N N 26.863 15.003 17.208 0.744 -0.787 -1.489 "C5'" 6FA 27 6FA "O5'" O5* O 0 1 N N N 27.222 13.732 17.739 0.666 0.103 -0.374 "O5'" 6FA 28 6FA P P P 0 1 N N R 26.659 12.407 17.068 1.159 -0.722 0.916 P 6FA 29 6FA O1P O1P O 0 1 N N N 27.095 11.285 17.972 0.278 -1.894 1.118 O1P 6FA 30 6FA O2P O2P O 0 1 N N N 25.217 12.564 16.740 2.672 -1.221 0.689 O2P 6FA 31 6FA O3P O3P O 0 1 N N N 27.333 12.388 15.610 1.096 0.225 2.216 O3P 6FA 32 6FA PA AP P 0 1 N N S 28.761 12.754 15.031 1.599 -0.659 3.463 PA 6FA 33 6FA O1A AO1 O 0 1 N N N 28.515 13.320 13.665 0.711 -1.832 3.625 O1A 6FA 34 6FA O2A AO2 O 0 1 N N N 29.581 13.491 16.034 3.105 -1.159 3.193 O2A 6FA 35 6FA O5B AO5* O 0 1 N N N 29.484 11.331 14.866 1.562 0.231 4.804 O5B 6FA 36 6FA C5B AC5* C 0 1 N N N 29.058 10.314 13.983 2.017 -0.606 5.868 C5B 6FA 37 6FA C4B AC4* C 0 1 N N R 30.215 9.412 13.587 2.006 0.184 7.179 C4B 6FA 38 6FA O4B AO4* O 0 1 N N N 29.713 8.278 12.912 0.665 0.600 7.487 O4B 6FA 39 6FA C3B AC3* C 0 1 N N S 31.368 9.928 12.887 2.488 -0.712 8.335 C3B 6FA 40 6FA O3B AO3* O 0 1 N N N 32.566 9.858 13.417 3.658 -0.165 8.947 O3B 6FA 41 6FA C2B AC2* C 0 1 N N R 31.266 9.307 11.598 1.301 -0.709 9.334 C2B 6FA 42 6FA O2B AO2* O 0 1 N N N 32.297 9.260 10.770 1.769 -0.616 10.681 O2B 6FA 43 6FA C1B AC1* C 0 1 N N R 30.545 8.101 11.789 0.536 0.575 8.925 C1B 6FA 44 6FA N9A AN9 N 0 1 Y N N 29.788 7.513 10.766 -0.873 0.486 9.315 N9A 6FA 45 6FA C8A AC8 C 0 1 Y N N 28.858 8.206 10.055 -1.875 -0.091 8.593 C8A 6FA 46 6FA N7A AN7 N 0 1 Y N N 28.232 7.390 9.183 -3.001 0.008 9.237 N7A 6FA 47 6FA C5X AC5 C 0 1 Y N N 28.802 6.180 9.287 -2.794 0.654 10.410 C5X 6FA 48 6FA C6A AC6 C 0 1 Y N N 28.601 4.910 8.606 -3.614 1.038 11.484 C6A 6FA 49 6FA N6A AN6 N 0 1 N N N 27.670 4.797 7.628 -4.969 0.755 11.477 N6A 6FA 50 6FA N1A AN1 N 0 1 Y N N 29.421 3.909 8.991 -3.059 1.679 12.507 N1A 6FA 51 6FA C2A AC2 C 0 1 Y N N 30.335 4.026 9.983 -1.767 1.952 12.523 C2A 6FA 52 6FA N3A AN3 N 0 1 Y N N 30.544 5.172 10.642 -0.961 1.612 11.539 N3A 6FA 53 6FA C4X AC4 C 0 1 Y N N 29.801 6.248 10.343 -1.425 0.963 10.476 C4X 6FA 54 6FA HN3 HN3 H 0 1 N N N 30.249 22.866 21.857 -5.353 -0.623 -8.998 HN3 6FA 55 6FA HO6 HO6 H 0 1 N N N 32.373 24.081 14.466 0.350 3.051 -11.226 HO6 6FA 56 6FA HM71 1HM7 H 0 0 N N N 31.903 21.501 11.913 3.383 3.296 -10.476 HM71 6FA 57 6FA HM72 2HM7 H 0 0 N N N 31.665 23.215 12.452 4.284 1.782 -10.727 HM72 6FA 58 6FA HM73 3HM7 H 0 0 N N N 32.982 22.321 13.115 2.997 2.251 -11.863 HM73 6FA 59 6FA HM81 1HM8 H 0 0 N N N 29.778 18.740 13.006 4.686 0.045 -8.893 HM81 6FA 60 6FA HM82 2HM8 H 0 0 N N N 29.913 20.280 12.044 4.619 1.820 -8.783 HM82 6FA 61 6FA HM83 3HM8 H 0 0 N N N 31.363 19.510 12.544 4.250 0.825 -7.354 HM83 6FA 62 6FA H9 H9 H 0 1 N N N 28.842 19.565 15.257 2.143 -0.334 -7.161 H9 6FA 63 6FA "H1'1" 1H1* H 0 0 N N N 26.929 20.186 17.968 -0.645 -2.102 -6.231 "H1'1" 6FA 64 6FA "H1'2" 2H1* H 0 0 N N N 27.496 19.720 16.408 1.027 -1.577 -6.534 "H1'2" 6FA 65 6FA "H2'" H2* H 0 1 N N N 28.255 18.532 19.126 -1.114 0.048 -5.090 "H2'" 6FA 66 6FA "HO2'" *HO2 H 0 0 N N N 29.964 17.474 18.022 1.658 0.500 -5.552 "HO2'" 6FA 67 6FA "H3'" H3* H 0 1 N N N 27.587 17.536 16.322 1.400 -1.350 -4.074 "H3'" 6FA 68 6FA "HO3'" *HO3 H 0 0 N N N 25.501 17.040 17.385 -1.372 -1.803 -3.611 "HO3'" 6FA 69 6FA "H4'" H4* H 0 1 N N N 27.578 16.074 18.967 -0.741 0.275 -2.630 "H4'" 6FA 70 6FA "HO4'" *HO4 H 0 0 N N N 29.306 14.838 17.804 2.031 0.728 -3.093 "HO4'" 6FA 71 6FA "H5'1" 1H5* H 0 0 N N N 25.775 15.221 17.317 0.100 -1.648 -1.311 "H5'1" 6FA 72 6FA "H5'2" 2H5* H 0 0 N N N 26.913 15.032 16.094 1.774 -1.123 -1.614 "H5'2" 6FA 73 6FA HOP2 2HOP H 0 0 N N N 24.880 11.771 16.338 3.212 -0.429 0.562 HOP2 6FA 74 6FA HOA2 2HOA H 0 0 N N N 30.437 13.710 15.686 3.650 -0.366 3.093 HOA2 6FA 75 6FA H51A AH51 H 0 0 N N N 28.209 9.729 14.409 1.358 -1.469 5.959 H51A 6FA 76 6FA H52A AH52 H 0 0 N N N 28.542 10.736 13.089 3.031 -0.944 5.657 H52A 6FA 77 6FA H4B AH4* H 0 1 N N N 30.667 9.202 14.584 2.654 1.056 7.091 H4B 6FA 78 6FA H3B AH3* H 0 1 N N N 31.310 11.041 12.900 2.683 -1.723 7.978 H3B 6FA 79 6FA HO3A AHO3 H 0 0 N N N 33.324 10.197 12.956 3.874 -0.735 9.698 HO3A 6FA 80 6FA H2B AH2* H 0 1 N N N 30.720 10.030 10.947 0.676 -1.593 9.201 H2B 6FA 81 6FA HO2A AHO2 H 0 0 N N N 32.229 8.848 9.916 2.234 -1.442 10.873 HO2A 6FA 82 6FA H1B AH1* H 0 1 N N N 31.373 7.359 11.878 1.000 1.456 9.367 H1B 6FA 83 6FA H8A AH8 H 0 1 N N N 28.641 9.281 10.169 -1.752 -0.561 7.629 H8A 6FA 84 6FA H61A AH61 H 0 0 N N N 27.529 3.906 7.150 -5.525 1.026 12.225 H61A 6FA 85 6FA H62A AH62 H 0 0 N N N 27.855 5.511 6.924 -5.363 0.287 10.725 H62A 6FA 86 6FA H2A AH2 H 0 1 N N N 30.937 3.146 10.267 -1.356 2.475 13.374 H2A 6FA 87 # 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 6FA N1 C2 SING N N 1 6FA N1 C10 DOUB N N 2 6FA C2 O2 DOUB N N 3 6FA C2 N3 SING N N 4 6FA N3 C4 SING N N 5 6FA N3 HN3 SING N N 6 6FA C4 O4 DOUB N N 7 6FA C4 C4A SING N N 8 6FA C4A N5 DOUB N N 9 6FA C4A C10 SING N N 10 6FA N5 C5A SING N N 11 6FA C5A C6 DOUB Y N 12 6FA C5A C9A SING Y N 13 6FA C6 O6 SING N N 14 6FA C6 C7 SING Y N 15 6FA O6 HO6 SING N N 16 6FA C7 C7M SING N N 17 6FA C7 C8 DOUB Y N 18 6FA C7M HM71 SING N N 19 6FA C7M HM72 SING N N 20 6FA C7M HM73 SING N N 21 6FA C8 C8M SING N N 22 6FA C8 C9 SING Y N 23 6FA C8M HM81 SING N N 24 6FA C8M HM82 SING N N 25 6FA C8M HM83 SING N N 26 6FA C9 C9A DOUB Y N 27 6FA C9 H9 SING N N 28 6FA C9A N10 SING N N 29 6FA N10 C10 SING N N 30 6FA N10 "C1'" SING N N 31 6FA "C1'" "C2'" SING N N 32 6FA "C1'" "H1'1" SING N N 33 6FA "C1'" "H1'2" SING N N 34 6FA "C2'" "O2'" SING N N 35 6FA "C2'" "C3'" SING N N 36 6FA "C2'" "H2'" SING N N 37 6FA "O2'" "HO2'" SING N N 38 6FA "C3'" "O3'" SING N N 39 6FA "C3'" "C4'" SING N N 40 6FA "C3'" "H3'" SING N N 41 6FA "O3'" "HO3'" SING N N 42 6FA "C4'" "O4'" SING N N 43 6FA "C4'" "C5'" SING N N 44 6FA "C4'" "H4'" SING N N 45 6FA "O4'" "HO4'" SING N N 46 6FA "C5'" "O5'" SING N N 47 6FA "C5'" "H5'1" SING N N 48 6FA "C5'" "H5'2" SING N N 49 6FA "O5'" P SING N N 50 6FA P O1P DOUB N N 51 6FA P O2P SING N N 52 6FA P O3P SING N N 53 6FA O2P HOP2 SING N N 54 6FA O3P PA SING N N 55 6FA PA O1A DOUB N N 56 6FA PA O2A SING N N 57 6FA PA O5B SING N N 58 6FA O2A HOA2 SING N N 59 6FA O5B C5B SING N N 60 6FA C5B C4B SING N N 61 6FA C5B H51A SING N N 62 6FA C5B H52A SING N N 63 6FA C4B O4B SING N N 64 6FA C4B C3B SING N N 65 6FA C4B H4B SING N N 66 6FA O4B C1B SING N N 67 6FA C3B O3B SING N N 68 6FA C3B C2B SING N N 69 6FA C3B H3B SING N N 70 6FA O3B HO3A SING N N 71 6FA C2B O2B SING N N 72 6FA C2B C1B SING N N 73 6FA C2B H2B SING N N 74 6FA O2B HO2A SING N N 75 6FA C1B N9A SING N N 76 6FA C1B H1B SING N N 77 6FA N9A C8A SING Y N 78 6FA N9A C4X SING Y N 79 6FA C8A N7A DOUB Y N 80 6FA C8A H8A SING N N 81 6FA N7A C5X SING Y N 82 6FA C5X C6A SING Y N 83 6FA C5X C4X DOUB Y N 84 6FA C6A N6A SING N N 85 6FA C6A N1A DOUB Y N 86 6FA N6A H61A SING N N 87 6FA N6A H62A SING N N 88 6FA N1A C2A SING Y N 89 6FA C2A N3A DOUB Y N 90 6FA C2A H2A SING N N 91 6FA N3A C4X SING Y N 92 # 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 6FA SMILES ACDLabs 10.04 "O=C2C3=Nc1c(cc(c(c1O)C)C)N(C3=NC(=O)N2)CC(O)C(O)C(O)COP(=O)(O)OP(=O)(O)OCC6OC(n5cnc4c(ncnc45)N)C(O)C6O" 6FA SMILES_CANONICAL CACTVS 3.341 "Cc1cc2N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)C6=NC(=O)NC(=O)C6=Nc2c(O)c1C" 6FA SMILES CACTVS 3.341 "Cc1cc2N(C[CH](O)[CH](O)[CH](O)CO[P](O)(=O)O[P](O)(=O)OC[CH]3O[CH]([CH](O)[CH]3O)n4cnc5c(N)ncnc45)C6=NC(=O)NC(=O)C6=Nc2c(O)c1C" 6FA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "Cc1cc2c(c(c1C)O)N=C3C(=O)NC(=O)N=C3N2C[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" 6FA SMILES "OpenEye OEToolkits" 1.5.0 "Cc1cc2c(c(c1C)O)N=C3C(=O)NC(=O)N=C3N2CC(C(C(COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)n5cnc6c5ncnc6N)O)O)O)O)O" 6FA InChI InChI 1.03 ;InChI=1S/C27H33N9O16P2/c1-9-3-11-15(18(39)10(9)2)32-17-24(33-27(44)34-25(17)43)35(11)4-12(37)19(40)13(38)5-49-53(45,46)52-54(47,48)50-6-14-20(41)21(42)26(51-14)36-8-31-16-22(28)29-7-30-23(16)36/h3,7-8,12-14,19-21,26,37-42H,4-6H2,1-2H3,(H,45,46)(H,47,48)(H2,28,29,30)(H,34,43,44)/t12-,13+,14+,19-,20+,21+,26+/m0/s1 ; 6FA InChIKey InChI 1.03 BJSUUWFQAMLNKU-OKXKTURISA-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 6FA "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)-2,3,4-trihydroxy-5-(6-hydroxy-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentyl dihydrogen diphosphate (non-preferred name)" 6FA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4S)-2,3,4-trihydroxy-5-(6-hydroxy-7,8-dimethyl-2,4-dioxo-benzo[g]pteridin-10-yl)pentyl] 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 6FA "Create component" 2001-11-29 RCSB 6FA "Modify descriptor" 2011-06-04 RCSB #