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                    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                        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 InChI            InChI                1.02b 
;InChI=1/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/f/h34,45,47H,28H2
;
6FA InChIKey         InChI                1.02b BJSUUWFQAMLNKU-OHIZLHPQDA 
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 
# 
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"                             
# 
