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                   2020-06-17
_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  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"  
EPU  InChI             InChI                 1.03   "InChI=1S/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"  
EPU  InChIKey          InChI                 1.03   BEGZZYPUNCJHKP-DBYWSUQTSA-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
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"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
EPU  "Create component"   1999-07-08  RCSB  
EPU  "Modify descriptor"  2011-06-04  RCSB  
EPU  "Modify synonyms"    2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     EPU
_pdbx_chem_comp_synonyms.name        ENOLPYRUVYL-URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
