data_EPU
# 
_chem_comp.id                                    EPU 
_chem_comp.name                                  "URIDINE-DIPHOSPHATE-2(N-ACETYLGLUCOSAMINYL) BUTYRIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C20 H29 N3 O19 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ENOLPYRUVYL-URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE 
_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                        677.400 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     EPU 
_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        1UXY 
_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 
EPU N1U    UN1  N 0 1 N N N 16.212 22.476 13.764 -0.970 0.803  6.848  N1U    EPU 1  
EPU C2U    UC2  C 0 1 N N N 17.593 22.445 13.744 -1.485 -0.408 6.574  C2U    EPU 2  
EPU N3U    UN3  N 0 1 N N N 18.155 21.241 13.583 -2.709 -0.755 7.013  N3U    EPU 3  
EPU C4U    UC4  C 0 1 N N N 17.480 20.088 13.448 -3.446 0.116  7.731  C4U    EPU 4  
EPU C5U    UC5  C 0 1 N N N 15.998 20.094 13.517 -2.918 1.397  8.022  C5U    EPU 5  
EPU C6U    UC6  C 0 1 N N N 15.369 21.277 13.665 -1.685 1.717  7.573  C6U    EPU 6  
EPU O2U    UO2  O 0 1 N N N 18.244 23.464 13.862 -0.832 -1.205 5.928  O2U    EPU 7  
EPU O4U    UO4  O 0 1 N N N 18.041 19.020 13.256 -4.556 -0.194 8.124  O4U    EPU 8  
EPU C1D    UC1* C 0 1 N N R 15.566 23.768 13.904 0.366  1.150  6.360  C1D    EPU 9  
EPU C2D    UC2* C 0 1 N N R 14.971 24.319 12.608 1.413  0.114  6.843  C2D    EPU 10 
EPU O2D    UO2* O 0 1 N N N 15.832 24.807 11.663 1.905  0.453  8.141  O2D    EPU 11 
EPU C3D    UC3* C 0 1 N N S 13.977 25.245 13.149 2.529  0.256  5.775  C3D    EPU 12 
EPU C4D    UC4* C 0 1 N N R 13.518 24.581 14.440 1.812  0.895  4.569  C4D    EPU 13 
EPU O4D    UO4* O 0 1 N N N 14.473 23.607 14.755 0.427  1.044  4.922  O4D    EPU 14 
EPU O3D    UO3* O 0 1 N N N 14.470 26.583 13.146 3.573  1.107  6.253  O3D    EPU 15 
EPU C5D    UC5* C 0 1 N N N 12.149 23.884 14.100 1.943  -0.012 3.345  C5D    EPU 16 
EPU O5D    UO5* O 0 1 N N N 12.387 22.919 13.008 1.270  0.584  2.235  O5D    EPU 17 
EPU PA     PA   P 0 1 N N R 11.127 22.235 12.408 1.447  -0.419 0.989  PA     EPU 18 
EPU O1A    O1A  O 0 1 N N N 10.621 23.379 11.570 2.888  -0.594 0.698  O1A    EPU 19 
EPU O2A    O2A  O 0 1 N N N 11.760 21.187 11.536 0.796  -1.846 1.352  O2A    EPU 20 
EPU O3A    O3A  O 0 1 N N N 9.970  21.648 13.190 0.709  0.194  -0.303 O3A    EPU 21 
EPU PB     PB   P 0 1 N N R 10.239 20.822 14.503 0.926  -0.855 -1.504 PB     EPU 22 
EPU O1B    O1B  O 0 1 N N N 9.755  21.585 15.719 0.335  -2.160 -1.132 O1B    EPU 23 
EPU O2B    O2B  O 0 1 N N N 11.667 20.333 14.622 2.501  -1.038 -1.779 O2B    EPU 24 
EPU C1     C1   C 0 1 N N R 7.987  19.800 14.419 0.436  -1.272 -3.860 C1     EPU 25 
EPU C2     C2   C 0 1 N N R 7.216  18.490 14.537 0.484  -0.573 -5.221 C2     EPU 26 
EPU C3     C3   C 0 1 N N R 7.188  17.699 13.254 -0.840 0.160  -5.455 C3     EPU 27 
EPU C4     C4   C 0 1 N N S 6.530  18.743 12.260 -1.991 -0.835 -5.271 C4     EPU 28 
EPU C5     C5   C 0 1 N N R 7.326  20.052 12.135 -1.852 -1.514 -3.907 C5     EPU 29 
EPU C6     C6   C 0 1 N N N 6.636  21.101 11.252 -3.016 -2.486 -3.703 C6     EPU 30 
EPU C7     C7   C 0 1 N N N 7.070  18.271 17.101 2.812  0.004  -5.650 C7     EPU 31 
EPU C8     C8   C 0 1 N N N 7.837  17.282 18.027 3.948  0.995  -5.667 C8     EPU 32 
EPU N2     N2   N 0 1 N N N 7.445  18.069 15.884 1.588  0.389  -5.238 N2     EPU 33 
EPU O1     O1   O 0 1 N N N 9.341  19.630 14.198 0.209  -0.302 -2.836 O1     EPU 34 
EPU O3     O3   O 0 1 N N N 6.430  16.617 13.633 -0.873 0.691  -6.781 O3     EPU 35 
EPU O4     O4   O 0 1 N N N 6.397  18.170 10.992 -3.239 -0.143 -5.336 O4     EPU 36 
EPU O5     O5   O 0 1 N N N 7.364  20.596 13.444 -0.620 -2.230 -3.846 O5     EPU 37 
EPU O6     O6   O 0 1 N N N 5.418  21.578 11.723 -2.893 -3.117 -2.427 O6     EPU 38 
EPU O7     O7   O 0 1 N N N 6.306  19.039 17.493 3.000  -1.139 -6.006 O7     EPU 39 
EPU C1E    EC1  C 0 1 N N N 6.334  14.374 14.296 -1.190 2.992  -5.987 C1E    EPU 40 
EPU O1E    EO1  O 0 1 N N N 6.625  13.146 14.146 -0.123 2.969  -5.406 O1E    EPU 41 
EPU O2E    EO2  O 0 1 N N N 5.549  14.750 15.233 -1.957 4.099  -5.944 O2E    EPU 42 
EPU C2E    EC2  C 0 1 N N N 6.906  15.382 13.358 -1.646 1.809  -6.738 C2E    EPU 43 
EPU C3E    EC3  C 0 1 N N N 7.764  15.083 12.359 -2.818 1.834  -7.375 C3E    EPU 44 
EPU HN3U   UHN3 H 0 0 N N N 19.173 21.199 13.561 -3.065 -1.634 6.810  HN3U   EPU 45 
EPU H5U    UH5  H 0 1 N N N 15.351 19.202 13.457 -3.493 2.109  8.595  H5U    EPU 46 
EPU H6U    UH6  H 0 1 N N N 14.266 21.265 13.701 -1.266 2.689  7.785  H6U    EPU 47 
EPU H1D    UH1* H 0 1 N N N 16.355 24.467 14.266 0.643  2.154  6.683  H1D    EPU 48 
EPU H2D    UH2* H 0 1 N N N 14.545 23.528 11.946 0.995  -0.892 6.839  H2D    EPU 49 
EPU HO2U   UHO2 H 0 0 N N N 15.462 25.149 10.857 2.549  -0.227 8.383  HO2U   EPU 50 
EPU H3D    UH3* H 0 1 N N N 13.055 25.411 12.543 2.927  -0.721 5.507  H3D    EPU 51 
EPU H4D    UH4* H 0 1 N N N 13.402 25.293 15.290 2.247  1.871  4.355  H4D    EPU 52 
EPU HO3U   UHO3 H 0 0 N N N 13.824 27.184 13.497 3.941  0.682  7.040  HO3U   EPU 53 
EPU "H5'1" 1H5* H 0 0 N N N 11.669 23.416 14.991 1.496  -0.982 3.563  "H5'1" EPU 54 
EPU "H5'2" 2H5* H 0 0 N N N 11.340 24.614 13.861 2.997  -0.145 3.102  "H5'2" EPU 55 
EPU HOA2   2HOA H 0 0 N N N 10.989 20.768 11.169 -0.139 -1.687 1.535  HOA2   EPU 56 
EPU HOB2   2HOB H 0 0 N N N 11.829 19.834 15.414 2.846  -0.167 -2.018 HOB2   EPU 57 
EPU H1     H1   H 0 1 N N N 7.948  20.325 15.401 1.385  -1.777 -3.678 H1     EPU 58 
EPU H2     H2   H 0 1 N N N 6.103  18.421 14.513 0.635  -1.314 -6.006 H2     EPU 59 
EPU H3     H3   H 0 1 N N N 8.113  17.312 12.766 -0.939 0.971  -4.734 H3     EPU 60 
EPU H4     H4   H 0 1 N N N 5.533  19.001 12.689 -1.950 -1.587 -6.059 H4     EPU 61 
EPU H5     H5   H 0 1 N N N 8.319  19.824 11.681 -1.871 -0.758 -3.122 H5     EPU 62 
EPU H61    1H6  H 0 1 N N N 7.329  21.952 11.060 -3.958 -1.940 -3.749 H61    EPU 63 
EPU H62    2H6  H 0 1 N N N 6.515  20.706 10.216 -2.997 -3.245 -4.486 H62    EPU 64 
EPU H81    1H8  H 0 1 N N N 7.512  17.456 19.079 4.852  0.504  -6.027 H81    EPU 65 
EPU H82    2H8  H 0 1 N N N 7.713  16.219 17.712 3.696  1.824  -6.329 H82    EPU 66 
EPU H83    3H8  H 0 1 N N N 8.943  17.351 17.903 4.116  1.373  -4.659 H83    EPU 67 
EPU HN2    HN2  H 0 1 N N N 8.147  17.344 16.035 1.438  1.304  -4.953 HN2    EPU 68 
EPU HO4    HO4  H 0 1 N N N 6.002  18.795 10.396 -3.933 -0.805 -5.211 HO4    EPU 69 
EPU HO6    HO6  H 0 1 N N N 4.991  22.227 11.176 -3.644 -3.719 -2.339 HO6    EPU 70 
EPU HO2E   EHO2 H 0 0 N N N 5.331  15.667 15.345 -1.658 4.876  -5.451 HO2E   EPU 71 
EPU HE31   1HE3 H 0 0 N N N 8.187  15.828 11.665 -3.395 2.747  -7.408 HE31   EPU 72 
EPU HE32   2HE3 H 0 0 N N N 8.152  14.075 12.134 -3.189 0.943  -7.859 HE32   EPU 73 
# 
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 
EPU N1U C2U    SING N N 1  
EPU N1U C6U    SING N N 2  
EPU N1U C1D    SING N N 3  
EPU C2U N3U    SING N N 4  
EPU C2U O2U    DOUB N N 5  
EPU N3U C4U    SING N N 6  
EPU N3U HN3U   SING N N 7  
EPU C4U C5U    SING N N 8  
EPU C4U O4U    DOUB N N 9  
EPU C5U C6U    DOUB N N 10 
EPU C5U H5U    SING N N 11 
EPU C6U H6U    SING N N 12 
EPU C1D C2D    SING N N 13 
EPU C1D O4D    SING N N 14 
EPU C1D H1D    SING N N 15 
EPU C2D O2D    SING N N 16 
EPU C2D C3D    SING N N 17 
EPU C2D H2D    SING N N 18 
EPU O2D HO2U   SING N N 19 
EPU C3D C4D    SING N N 20 
EPU C3D O3D    SING N N 21 
EPU C3D H3D    SING N N 22 
EPU C4D O4D    SING N N 23 
EPU C4D C5D    SING N N 24 
EPU C4D H4D    SING N N 25 
EPU O3D HO3U   SING N N 26 
EPU C5D O5D    SING N N 27 
EPU C5D "H5'1" SING N N 28 
EPU C5D "H5'2" SING N N 29 
EPU O5D PA     SING N N 30 
EPU PA  O1A    DOUB N N 31 
EPU PA  O2A    SING N N 32 
EPU PA  O3A    SING N N 33 
EPU O2A HOA2   SING N N 34 
EPU O3A PB     SING N N 35 
EPU PB  O1B    DOUB N N 36 
EPU PB  O2B    SING N N 37 
EPU PB  O1     SING N N 38 
EPU O2B HOB2   SING N N 39 
EPU C1  C2     SING N N 40 
EPU C1  O1     SING N N 41 
EPU C1  O5     SING N N 42 
EPU C1  H1     SING N N 43 
EPU C2  C3     SING N N 44 
EPU C2  N2     SING N N 45 
EPU C2  H2     SING N N 46 
EPU C3  C4     SING N N 47 
EPU C3  O3     SING N N 48 
EPU C3  H3     SING N N 49 
EPU C4  C5     SING N N 50 
EPU C4  O4     SING N N 51 
EPU C4  H4     SING N N 52 
EPU C5  C6     SING N N 53 
EPU C5  O5     SING N N 54 
EPU C5  H5     SING N N 55 
EPU C6  O6     SING N N 56 
EPU C6  H61    SING N N 57 
EPU C6  H62    SING N N 58 
EPU C7  C8     SING N N 59 
EPU C7  N2     SING N N 60 
EPU C7  O7     DOUB N N 61 
EPU C8  H81    SING N N 62 
EPU C8  H82    SING N N 63 
EPU C8  H83    SING N N 64 
EPU N2  HN2    SING N N 65 
EPU O3  C2E    SING N N 66 
EPU O4  HO4    SING N N 67 
EPU O6  HO6    SING N N 68 
EPU C1E O1E    DOUB N N 69 
EPU C1E O2E    SING N N 70 
EPU C1E C2E    SING N N 71 
EPU O2E HO2E   SING N N 72 
EPU C2E C3E    DOUB N N 73 
EPU C3E HE31   SING N N 74 
EPU C3E HE32   SING N N 75 
# 
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 
EPU SMILES           ACDLabs              10.04 O=P(OC1OC(C(O)C(O/C(=C)C(=O)O)C1NC(=O)C)CO)(O)OP(=O)(O)OCC3OC(N2C=CC(=O)NC2=O)C(O)C3O 
EPU InChI            InChI                1.02b 
;InChI=1/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1/f/h21-22,30,33,35H
;
EPU InChIKey         InChI                1.02b BEGZZYPUNCJHKP-PVKYKPMBDI 
EPU SMILES_CANONICAL CACTVS               3.341 CC(=O)N[C@H]1[C@H](O[C@H](CO)[C@@H](O)[C@@H]1OC(=C)C(O)=O)O[P@](O)(=O)O[P@@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O 
EPU SMILES           CACTVS               3.341 CC(=O)N[CH]1[CH](O[CH](CO)[CH](O)[CH]1OC(=C)C(O)=O)O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O 
EPU SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)OC(=C)C(=O)O 
EPU SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)NC1C(C(C(OC1OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)CO)O)OC(=C)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 
EPU "SYSTEMATIC NAME" ACDLabs              10.04 
;2-{[(2R,3R,4R,5S,6R)-3-(acetylamino)-2-{[(R)-{[(R)-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]oxy}-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}prop-2-enoic acid (non-preferred name)
;
EPU "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"2-[(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxyprop-2-enoic acid" 
# 
