data_KEU
# 
_chem_comp.id                                    KEU 
_chem_comp.name                                  "N-{4-[(1R)-4-[(2R,4R,5S)-2,4-DIAMINO-6-OXOHEXAHYDROPYRIMIDIN-5-YL]-1-(2,2,2-TRIFLUORO-1,1-DIHYDROXYETHYL)BUTYL]BENZOYL}-D-GLUTAMIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H30 F3 N5 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "10-CF3C(OH)2-DDACTHF, HYDROLYZED FORM OF 10-TRIFLUOROACETYL-5,10-DIDEAZA-ACYCLIC-5,6,7,8-TETRAHYDROFOLIC ACID" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-02-20 
_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                        549.498 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     KEU 
_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        1NJS 
_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 
KEU O4   O4   O 0 1 N N N 72.840 19.045 38.006 1.904  2.600  7.830  O4   KEU 1  
KEU C21  C21  C 0 1 N N N 74.142 19.161 37.833 0.632  2.189  7.714  C21  KEU 2  
KEU O5   O5   O 0 1 N N N 74.997 18.317 38.113 -0.253 2.803  8.260  O5   KEU 3  
KEU C20  C20  C 0 1 N N N 74.461 20.478 37.250 0.308  0.961  6.903  C20  KEU 4  
KEU C19  C19  C 0 1 N N N 75.956 20.703 37.035 -1.200 0.713  6.932  C19  KEU 5  
KEU C17  C17  C 0 1 N N S 76.279 22.033 36.447 -1.529 -0.533 6.109  C17  KEU 6  
KEU N    N    N 0 1 N N N 75.558 22.007 35.120 -1.094 -0.332 4.724  N    KEU 7  
KEU C    C    C 0 1 N N N 74.615 22.967 34.790 -0.707 -1.387 3.980  C    KEU 8  
KEU O    O    O 0 1 N N N 74.311 23.853 35.557 -0.720 -2.505 4.457  O    KEU 9  
KEU C14  C14  C 0 1 Y N N 74.025 22.910 33.476 -0.268 -1.185 2.582  C14  KEU 10 
KEU C13  C13  C 0 1 Y N N 73.094 24.028 33.132 0.131  -2.275 1.809  C13  KEU 11 
KEU C12  C12  C 0 1 Y N N 72.506 24.094 31.819 0.539  -2.079 0.505  C12  KEU 12 
KEU C11  C11  C 0 1 Y N N 72.864 22.976 30.820 0.552  -0.806 -0.034 C11  KEU 13 
KEU C16  C16  C 0 1 Y N N 73.762 21.877 31.214 0.161  0.279  0.729  C16  KEU 14 
KEU C15  C15  C 0 1 Y N N 74.346 21.827 32.503 -0.253 0.097  2.031  C15  KEU 15 
KEU C10  C10  C 0 1 N N R 72.364 22.916 29.274 1.000  -0.599 -1.458 C10  KEU 16 
KEU C1   C1   C 0 1 N N N 73.431 22.236 28.398 -0.044 0.231  -2.205 C1   KEU 17 
KEU C2   C2   C 0 1 N N N 74.479 23.545 28.109 0.329  0.307  -3.687 C2   KEU 18 
KEU C3   C3   C 0 1 N N N 75.256 23.531 26.741 -0.782 1.022  -4.457 C3   KEU 19 
KEU C4   C4   C 0 1 N N S 76.515 24.210 27.183 -0.456 1.010  -5.952 C4   KEU 20 
KEU C9   C9   C 0 1 N N N 76.407 25.512 26.878 -1.481 1.822  -6.700 C9   KEU 21 
KEU O1   O1   O 0 1 N N N 75.406 26.283 26.270 -1.811 2.905  -6.265 O1   KEU 22 
KEU N3   N3   N 0 1 N N N 77.519 26.643 27.167 -2.035 1.374  -7.833 N3   KEU 23 
KEU C8   C8   C 0 1 N N R 78.653 26.213 27.769 -1.711 0.078  -8.417 C8   KEU 24 
KEU N2   N2   N 0 1 N N N 79.646 27.065 28.061 -2.750 -0.891 -8.046 N2   KEU 25 
KEU N1   N1   N 0 1 N N N 78.796 24.990 28.038 -0.412 -0.401 -7.939 N1   KEU 26 
KEU C7   C7   C 0 1 N N S 77.809 23.914 27.821 -0.484 -0.430 -6.471 C7   KEU 27 
KEU N8   N8   N 0 1 N N N 78.134 22.633 28.205 -1.730 -1.084 -6.051 N8   KEU 28 
KEU C5   C5   C 0 1 N N N 70.959 22.346 28.843 2.341  0.136  -1.470 C5   KEU 29 
KEU OA2  OA2  O 0 1 N N N 70.495 22.747 27.853 2.793  0.281  -2.817 OA2  KEU 30 
KEU OA1  OA1  O 0 1 N N N 70.073 23.139 29.911 2.180  1.428  -0.879 OA1  KEU 31 
KEU C6   C6   C 0 1 N N N 70.564 20.933 29.329 3.370  -0.665 -0.670 C6   KEU 32 
KEU F2   F2   F 0 1 N N N 70.665 20.605 30.673 4.626  -0.062 -0.790 F2   KEU 33 
KEU F1   F1   F 0 1 N N N 71.515 20.214 28.743 2.993  -0.694 0.676  F1   KEU 34 
KEU F    F    F 0 1 N N N 69.333 20.634 28.881 3.430  -1.971 -1.166 F    KEU 35 
KEU C18  C18  C 0 1 N N N 77.824 22.367 36.249 -3.016 -0.777 6.138  C18  KEU 36 
KEU O3   O3   O 0 1 N N N 78.454 22.790 37.205 -3.498 -1.469 7.003  O3   KEU 37 
KEU O2   O2   O 0 1 N N N 78.442 22.183 35.030 -3.804 -0.226 5.202  O2   KEU 38 
KEU HO4  HO4  H 0 1 N N N 72.181 19.695 37.790 2.112  3.388  8.351  HO4  KEU 39 
KEU H201 1H20 H 0 0 N N N 73.897 20.636 36.301 0.826  0.099  7.325  H201 KEU 40 
KEU H202 2H20 H 0 0 N N N 74.022 21.298 37.864 0.632  1.110  5.873  H202 KEU 41 
KEU H191 1H19 H 0 0 N N N 76.519 20.544 37.984 -1.718 1.574  6.510  H191 KEU 42 
KEU H192 2H19 H 0 0 N N N 76.393 19.882 36.419 -1.524 0.564  7.962  H192 KEU 43 
KEU H17  H17  H 0 1 N N N 75.961 22.840 37.147 -1.011 -1.394 6.531  H17  KEU 44 
KEU HN   HN   H 0 1 N N N 75.717 21.298 34.403 -1.083 0.559  4.344  HN   KEU 45 
KEU H13  H13  H 0 1 N N N 72.836 24.816 33.858 0.121  -3.270 2.229  H13  KEU 46 
KEU H12  H12  H 0 1 N N N 71.831 24.937 31.595 0.849  -2.922 -0.094 H12  KEU 47 
KEU H16  H16  H 0 1 N N N 74.006 21.058 30.516 0.174  1.271  0.301  H16  KEU 48 
KEU H15  H15  H 0 1 N N N 75.018 20.984 32.737 -0.562 0.944  2.625  H15  KEU 49 
KEU H10  H10  H 0 1 N N N 72.207 24.009 29.119 1.112  -1.567 -1.947 H10  KEU 50 
KEU H11  1H1  H 0 1 N N N 73.905 21.326 28.834 -0.076 1.237  -1.787 H11  KEU 51 
KEU H12A 2H1  H 0 0 N N N 73.048 21.715 27.489 -1.023 -0.236 -2.101 H12A KEU 52 
KEU H21  1H2  H 0 1 N N N 73.919 24.504 28.213 0.454  -0.700 -4.082 H21  KEU 53 
KEU H22  2H2  H 0 1 N N N 75.203 23.639 28.951 1.262  0.860  -3.798 H22  KEU 54 
KEU H31  1H3  H 0 1 N N N 75.376 22.536 26.251 -0.859 2.053  -4.111 H31  KEU 55 
KEU H32  2H3  H 0 1 N N N 74.729 23.985 25.869 -1.729 0.510  -4.288 H32  KEU 56 
KEU H4   H4   H 0 1 N N N 76.659 23.146 27.483 0.534  1.436  -6.113 H4   KEU 57 
KEU HN3  HN3  H 0 1 N N N 77.504 27.643 26.966 -2.682 1.937  -8.287 HN3  KEU 58 
KEU H8   H8   H 0 1 N N N 77.976 26.913 28.312 -1.681 0.173  -9.503 H8   KEU 59 
KEU HN21 1HN2 H 0 0 N N N 80.500 26.741 28.514 -3.623 -0.531 -8.402 HN21 KEU 60 
KEU HN22 2HN2 H 0 0 N N N 79.257 27.823 28.621 -2.554 -1.736 -8.560 HN22 KEU 61 
KEU HN1  HN1  H 0 1 N N N 79.050 24.945 29.024 -0.327 -1.359 -8.244 HN1  KEU 62 
KEU H7   H7   H 0 1 N N N 76.734 23.950 28.115 0.369  -0.978 -6.073 H7   KEU 63 
KEU HN61 1HN6 H 0 0 N N N 79.030 22.428 28.646 -1.706 -2.021 -6.427 HN61 KEU 64 
KEU HN62 2HN6 H 0 0 N N N 78.035 22.024 27.392 -1.687 -1.173 -5.047 HN62 KEU 65 
KEU HA2  HA2  H 0 1 N N N 69.648 22.403 27.593 2.888  -0.610 -3.178 HA2  KEU 66 
KEU HA1  HA1  H 0 1 N N N 69.226 22.795 29.651 2.002  1.285  0.060  HA1  KEU 67 
KEU HO2  HO2  H 0 1 N N N 79.363 22.382 34.911 -4.759 -0.382 5.221  HO2  KEU 68 
# 
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 
KEU O4  C21  SING N N 1  
KEU O4  HO4  SING N N 2  
KEU C21 O5   DOUB N N 3  
KEU C21 C20  SING N N 4  
KEU C20 C19  SING N N 5  
KEU C20 H201 SING N N 6  
KEU C20 H202 SING N N 7  
KEU C19 C17  SING N N 8  
KEU C19 H191 SING N N 9  
KEU C19 H192 SING N N 10 
KEU C17 N    SING N N 11 
KEU C17 C18  SING N N 12 
KEU C17 H17  SING N N 13 
KEU N   C    SING N N 14 
KEU N   HN   SING N N 15 
KEU C   O    DOUB N N 16 
KEU C   C14  SING N N 17 
KEU C14 C13  DOUB Y N 18 
KEU C14 C15  SING Y N 19 
KEU C13 C12  SING Y N 20 
KEU C13 H13  SING N N 21 
KEU C12 C11  DOUB Y N 22 
KEU C12 H12  SING N N 23 
KEU C11 C16  SING Y N 24 
KEU C11 C10  SING N N 25 
KEU C16 C15  DOUB Y N 26 
KEU C16 H16  SING N N 27 
KEU C15 H15  SING N N 28 
KEU C10 C1   SING N N 29 
KEU C10 C5   SING N N 30 
KEU C10 H10  SING N N 31 
KEU C1  C2   SING N N 32 
KEU C1  H11  SING N N 33 
KEU C1  H12A SING N N 34 
KEU C2  C3   SING N N 35 
KEU C2  H21  SING N N 36 
KEU C2  H22  SING N N 37 
KEU C3  C4   SING N N 38 
KEU C3  H31  SING N N 39 
KEU C3  H32  SING N N 40 
KEU C4  C9   SING N N 41 
KEU C4  C7   SING N N 42 
KEU C4  H4   SING N N 43 
KEU C9  O1   DOUB N N 44 
KEU C9  N3   SING N N 45 
KEU N3  C8   SING N N 46 
KEU N3  HN3  SING N N 47 
KEU C8  N2   SING N N 48 
KEU C8  N1   SING N N 49 
KEU C8  H8   SING N N 50 
KEU N2  HN21 SING N N 51 
KEU N2  HN22 SING N N 52 
KEU N1  C7   SING N N 53 
KEU N1  HN1  SING N N 54 
KEU C7  N8   SING N N 55 
KEU C7  H7   SING N N 56 
KEU N8  HN61 SING N N 57 
KEU N8  HN62 SING N N 58 
KEU C5  OA2  SING N N 59 
KEU C5  OA1  SING N N 60 
KEU C5  C6   SING N N 61 
KEU OA2 HA2  SING N N 62 
KEU OA1 HA1  SING N N 63 
KEU C6  F2   SING N N 64 
KEU C6  F1   SING N N 65 
KEU C6  F    SING N N 66 
KEU C18 O3   DOUB N N 67 
KEU C18 O2   SING N N 68 
KEU O2  HO2  SING N N 69 
# 
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 
KEU SMILES           ACDLabs              10.04 O=C1NC(N)NC(N)C1CCCC(c2ccc(C(=O)NC(C(=O)O)CCC(=O)O)cc2)C(O)(O)C(F)(F)F 
KEU InChI            InChI                1.02b 
;InChI=1/C22H30F3N5O8/c23-22(24,25)21(37,38)13(3-1-2-12-16(26)29-20(27)30-18(12)34)10-4-6-11(7-5-10)17(33)28-14(19(35)36)8-9-15(31)32/h4-7,12-14,16,20,29,37-38H,1-3,8-9,26-27H2,(H,28,33)(H,30,34)(H,31,32)(H,35,36)/t12?,13-,14+,16+,20-/m1/s1/f/h28,30-31,35H
;
KEU InChIKey         InChI                1.02b KOLDLUFBEMUZIM-DMTFEZEZDF 
KEU SMILES_CANONICAL CACTVS               3.341 N[C@@H]1N[C@H](N)[C@H](CCC[C@H](c2ccc(cc2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)(O)C(F)(F)F)C(=O)N1 
KEU SMILES           CACTVS               3.341 N[CH]1N[CH](N)[CH](CCC[CH](c2ccc(cc2)C(=O)N[CH](CCC(O)=O)C(O)=O)C(O)(O)C(F)(F)F)C(=O)N1 
KEU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(ccc1[C@@H](CCCC2C(NC(NC2=O)N)N)C(C(F)(F)F)(O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)O 
KEU SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(ccc1C(CCCC2C(NC(NC2=O)N)N)C(C(F)(F)F)(O)O)C(=O)NC(CCC(=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 
KEU "SYSTEMATIC NAME" ACDLabs              10.04 "N-({4-[(1R)-4-[(2R,4S,5S)-2,4-diamino-6-oxohexahydropyrimidin-5-yl]-1-(2,2,2-trifluoro-1,1-dihydroxyethyl)butyl]phenyl}carbonyl)-L-glutamic acid" 
KEU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-[[4-[(3R)-6-(2,4-diamino-6-oxo-1,3-diazinan-5-yl)-1,1,1-trifluoro-2,2-dihydroxy-hexan-3-yl]phenyl]carbonylamino]pentanedioic acid"         
# 
