data_EEB
# 
_chem_comp.id                                    EEB 
_chem_comp.name                                  "URIDINE-DIPHOSPHATE-3(N-ACETYLGLUCOSAMINYL)BUTYRIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             ATOMS 
_chem_comp.formula                               "C21 H33 N3 O19 P2" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_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                        693.443 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     EEB 
_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        1MBB 
_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 
EEB N1U    UN1  N 0 1 N N N 16.497 22.571 13.942 1.030  0.901  -7.064 N1U    EEB 1  
EEB C2U    UC2  C 0 1 N N N 17.880 22.647 13.863 1.571  -0.301 -6.800 C2U    EEB 2  
EEB N3U    UN3  N 0 1 N N N 18.529 21.488 13.661 2.809  -0.611 -7.226 N3U    EEB 3  
EEB C4U    UC4  C 0 1 N N N 17.948 20.281 13.564 3.535  0.289  -7.919 C4U    EEB 4  
EEB C5U    UC5  C 0 1 N N N 16.468 20.169 13.654 2.980  1.561  -8.199 C5U    EEB 5  
EEB C6U    UC6  C 0 1 N N N 15.751 21.304 13.863 1.733  1.843  -7.764 C6U    EEB 6  
EEB O2U    UO2  O 0 1 N N N 18.460 23.704 13.968 0.928  -1.124 -6.177 O2U    EEB 7  
EEB O4U    UO4  O 0 1 N N N 18.597 19.257 13.410 4.658  0.011  -8.300 O4U    EEB 8  
EEB C1D    UC1* C 0 1 N N R 15.752 23.807 14.149 -0.322 1.208  -6.592 C1D    EEB 9  
EEB C2D    UC2* C 0 1 N N R 15.119 24.407 12.896 -1.335 0.153  -7.107 C2D    EEB 10 
EEB O2D    UO2* O 0 1 N N N 15.929 25.015 11.979 -1.816 0.500  -8.407 O2D    EEB 11 
EEB C3D    UC3* C 0 1 N N S 14.053 25.223 13.486 -2.470 0.252  -6.054 C3D    EEB 12 
EEB C4D    UC4* C 0 1 N N R 13.671 24.480 14.767 -1.788 0.890  -4.828 C4D    EEB 13 
EEB O4D    UO4* O 0 1 N N N 14.669 23.519 14.991 -0.401 1.078  -5.157 O4D    EEB 14 
EEB O3D    UO3* O 0 1 N N N 14.395 26.614 13.493 -3.528 1.084  -6.535 O3D    EEB 15 
EEB C5D    UC5* C 0 1 N N N 12.317 23.739 14.429 -1.915 -0.039 -3.619 C5D    EEB 16 
EEB O5D    UO5* O 0 1 N N N 12.605 22.881 13.256 -1.273 0.556  -2.490 O5D    EEB 17 
EEB PA     PA   P 0 1 N N R 11.419 22.196 12.516 -1.444 -0.470 -1.262 PA     EEB 18 
EEB O1A    O1A  O 0 1 N N N 10.882 23.404 11.761 -2.884 -0.684 -0.996 O1A    EEB 19 
EEB O2A    O2A  O 0 1 N N N 12.203 21.286 11.593 -0.752 -1.874 -1.637 O2A    EEB 20 
EEB O3A    O3A  O 0 1 N N N 10.268 21.440 13.128 -0.741 0.141  0.050  O3A    EEB 21 
EEB PB     PB   P 0 1 N N R 10.502 20.736 14.492 -0.949 -0.931 1.232  PB     EEB 22 
EEB O1B    O1B  O 0 1 N N N 10.071 21.634 15.629 -0.321 -2.215 0.849  O1B    EEB 23 
EEB O2B    O2B  O 0 1 N N N 11.914 20.206 14.617 -2.524 -1.157 1.480  O2B    EEB 24 
EEB C1     C1   C 0 1 N N R 8.212  19.870 14.659 -0.485 -1.372 3.589  C1     EEB 25 
EEB C2     C2   C 0 1 N N R 7.289  18.673 14.790 -0.580 -0.690 4.956  C2     EEB 26 
EEB C3     C3   C 0 1 N N R 7.283  17.890 13.490 0.721  0.073  5.224  C3     EEB 27 
EEB C4     C4   C 0 1 N N S 6.620  19.004 12.538 1.902  -0.887 5.052  C4     EEB 28 
EEB C5     C5   C 0 1 N N R 7.436  20.317 12.455 1.808  -1.551 3.676  C5     EEB 29 
EEB C6     C6   C 0 1 N N N 6.708  21.457 11.679 3.001  -2.489 3.481  C6     EEB 30 
EEB C7     C7   C 0 1 N N N 6.951  18.501 17.386 -2.933 -0.187 5.342  C7     EEB 31 
EEB C8     C8   C 0 1 N N N 7.665  17.522 18.339 -4.098 0.768  5.348  C8     EEB 32 
EEB N2     N2   N 0 1 N N N 7.406  18.278 16.168 -1.713 0.239  4.962  N2     EEB 33 
EEB O1     O1   O 0 1 N N N 9.538  19.578 14.356 -0.267 -0.381 2.582  O1     EEB 34 
EEB O3     O3   O 0 1 N N N 6.554  16.765 13.822 0.710  0.585  6.558  O3     EEB 35 
EEB O4     O4   O 0 1 N N N 6.436  18.542 11.234 3.128  -0.160 5.151  O4     EEB 36 
EEB O5     O5   O 0 1 N N N 7.588  20.771 13.786 0.597  -2.300 3.583  O5     EEB 37 
EEB O6     O6   O 0 1 N N N 5.549  21.994 12.299 2.914  -3.110 2.197  O6     EEB 38 
EEB O7     O7   O 0 1 N N N 6.156  19.280 17.763 -3.094 -1.341 5.679  O7     EEB 39 
EEB C1E    EC1  C 0 1 N N N 6.572  14.455 14.299 0.604  2.960  6.244  C1E    EEB 40 
EEB C2E    EC2  C 0 1 N N R 7.027  15.569 13.389 1.492  1.781  6.548  C2E    EEB 41 
EEB C3E    EC3  C 0 1 N N N 7.796  15.412 12.272 2.145  1.975  7.918  C3E    EEB 42 
EEB C4E    EC4  C 0 1 N N N 8.345  14.118 11.758 3.047  0.778  8.226  C4E    EEB 43 
EEB O1E    EO1  O 0 1 N N N 6.865  13.231 14.031 -0.577 2.793  6.055  O1E    EEB 44 
EEB O2E    EO2  O 0 1 N N N 5.880  14.736 15.349 1.125  4.195  6.183  O2E    EEB 45 
EEB HN3U   UHN3 H 0 0 N N N 19.544 21.527 13.574 3.183  -1.485 -7.030 HN3U   EEB 46 
EEB H5U    UH5  H 0 1 N N N 15.894 19.231 13.564 3.546  2.295  -8.753 H5U    EEB 47 
EEB H6U    UH6  H 0 1 N N N 14.656 21.205 13.960 1.293  2.808  -7.969 H6U    EEB 48 
EEB H1D    UH1* H 0 1 N N N 16.497 24.534 14.547 -0.618 2.209  -6.904 H1D    EEB 49 
EEB H2D    UH2* H 0 1 N N N 14.758 23.625 12.187 -0.892 -0.842 -7.111 H2D    EEB 50 
EEB HO2U   UHO2 H 0 0 N N N 15.535 25.388 11.199 -2.439 -0.191 -8.668 HO2U   EEB 51 
EEB H3D    UH3* H 0 1 N N N 13.106 25.317 12.904 -2.849 -0.738 -5.806 H3D    EEB 52 
EEB H4D    UH4* H 0 1 N N N 13.567 25.145 15.655 -2.250 1.852  -4.605 H4D    EEB 53 
EEB HO3U   UHO3 H 0 0 N N N 13.704 27.142 13.875 -3.873 0.663  -7.334 HO3U   EEB 54 
EEB "H5'1" 1H5* H 0 0 N N N 11.886 23.181 15.293 -1.440 -0.994 -3.845 "H5'1" EEB 55 
EEB "H5'2" 2H5* H 0 0 N N N 11.457 24.431 14.273 -2.969 -0.201 -3.395 "H5'2" EEB 56 
EEB HOA2   2HOA H 0 0 N N N 11.479 20.868 11.141 0.181  -1.690 -1.802 HOA2   EEB 57 
EEB HOB2   2HOB H 0 0 N N N 12.057 19.775 15.451 -2.894 -0.298 1.727  HOB2   EEB 58 
EEB H1     H1   H 0 1 N N N 8.345  20.342 15.660 -1.416 -1.900 3.382  H1     EEB 59 
EEB H2     H2   H 0 1 N N N 6.174  18.675 14.765 -0.723 -1.443 5.730  H2     EEB 60 
EEB H3     H3   H 0 1 N N N 8.203  17.502 12.993 0.813  0.897  4.517  H3     EEB 61 
EEB H4     H4   H 0 1 N N N 5.637  19.217 13.019 1.867  -1.651 5.828  H4     EEB 62 
EEB H5     H5   H 0 1 N N N 8.389  20.097 11.920 1.820  -0.784 2.902  H5     EEB 63 
EEB H61    1H6  H 0 1 N N N 7.427  22.277 11.449 3.927  -1.918 3.547  H61    EEB 64 
EEB H62    2H6  H 0 1 N N N 6.459  21.113 10.647 2.991  -3.255 4.256  H62    EEB 65 
EEB H81    1H8  H 0 1 N N N 7.280  17.710 19.368 -4.995 0.246  5.682  H81    EEB 66 
EEB H82    2H8  H 0 1 N N N 7.559  16.457 18.025 -3.885 1.595  6.026  H82    EEB 67 
EEB H83    3H8  H 0 1 N N N 8.776  17.585 18.273 -4.256 1.155  4.341  H83    EEB 68 
EEB HN2    HN2  H 0 1 N N N 8.086  17.542 16.358 -1.584 1.162  4.692  HN2    EEB 69 
EEB HO4    HO4  H 0 1 N N N 6.044  19.200 10.671 3.843  -0.802 5.037  HO4    EEB 70 
EEB HO6    HO6  H 0 1 N N N 5.105  22.688 11.826 3.683  -3.691 2.115  HO6    EEB 71 
EEB H2E    EH2  H 0 1 N N N 7.726  15.344 12.550 2.266  1.703  5.784  H2E    EEB 72 
EEB HE31   1HE3 H 0 0 N N N 7.225  15.868 11.430 1.372  2.053  8.682  HE31   EEB 73 
EEB HE32   2HE3 H 0 0 N N N 8.666  16.098 12.389 2.742  2.887  7.910  HE32   EEB 74 
EEB HE41   1HE4 H 0 0 N N N 8.973  13.989 10.845 3.513  0.916  9.202  HE41   EEB 75 
EEB HE42   2HE4 H 0 0 N N N 8.915  13.661 12.600 2.451  -0.133 8.234  HE42   EEB 76 
EEB HE43   3HE4 H 0 0 N N N 7.474  13.431 11.640 3.821  0.700  7.463  HE43   EEB 77 
EEB HO2E   EHO2 H 0 0 N N N 5.593  14.034 15.922 0.555  4.952  5.988  HO2E   EEB 78 
# 
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 
EEB N1U C2U    SING N N 1  
EEB N1U C6U    SING N N 2  
EEB N1U C1D    SING N N 3  
EEB C2U N3U    SING N N 4  
EEB C2U O2U    DOUB N N 5  
EEB N3U C4U    SING N N 6  
EEB N3U HN3U   SING N N 7  
EEB C4U C5U    SING N N 8  
EEB C4U O4U    DOUB N N 9  
EEB C5U C6U    DOUB N N 10 
EEB C5U H5U    SING N N 11 
EEB C6U H6U    SING N N 12 
EEB C1D C2D    SING N N 13 
EEB C1D O4D    SING N N 14 
EEB C1D H1D    SING N N 15 
EEB C2D O2D    SING N N 16 
EEB C2D C3D    SING N N 17 
EEB C2D H2D    SING N N 18 
EEB O2D HO2U   SING N N 19 
EEB C3D C4D    SING N N 20 
EEB C3D O3D    SING N N 21 
EEB C3D H3D    SING N N 22 
EEB C4D O4D    SING N N 23 
EEB C4D C5D    SING N N 24 
EEB C4D H4D    SING N N 25 
EEB O3D HO3U   SING N N 26 
EEB C5D O5D    SING N N 27 
EEB C5D "H5'1" SING N N 28 
EEB C5D "H5'2" SING N N 29 
EEB O5D PA     SING N N 30 
EEB PA  O1A    DOUB N N 31 
EEB PA  O2A    SING N N 32 
EEB PA  O3A    SING N N 33 
EEB O2A HOA2   SING N N 34 
EEB O3A PB     SING N N 35 
EEB PB  O1B    DOUB N N 36 
EEB PB  O2B    SING N N 37 
EEB PB  O1     SING N N 38 
EEB O2B HOB2   SING N N 39 
EEB C1  C2     SING N N 40 
EEB C1  O1     SING N N 41 
EEB C1  O5     SING N N 42 
EEB C1  H1     SING N N 43 
EEB C2  C3     SING N N 44 
EEB C2  N2     SING N N 45 
EEB C2  H2     SING N N 46 
EEB C3  C4     SING N N 47 
EEB C3  O3     SING N N 48 
EEB C3  H3     SING N N 49 
EEB C4  C5     SING N N 50 
EEB C4  O4     SING N N 51 
EEB C4  H4     SING N N 52 
EEB C5  C6     SING N N 53 
EEB C5  O5     SING N N 54 
EEB C5  H5     SING N N 55 
EEB C6  O6     SING N N 56 
EEB C6  H61    SING N N 57 
EEB C6  H62    SING N N 58 
EEB C7  C8     SING N N 59 
EEB C7  N2     SING N N 60 
EEB C7  O7     DOUB N N 61 
EEB C8  H81    SING N N 62 
EEB C8  H82    SING N N 63 
EEB C8  H83    SING N N 64 
EEB N2  HN2    SING N N 65 
EEB O3  C2E    SING N N 66 
EEB O4  HO4    SING N N 67 
EEB O6  HO6    SING N N 68 
EEB C1E C2E    SING N N 69 
EEB C1E O1E    DOUB N N 70 
EEB C1E O2E    SING N N 71 
EEB C2E C3E    SING N N 72 
EEB C2E H2E    SING N N 73 
EEB C3E C4E    SING N N 74 
EEB C3E HE31   SING N N 75 
EEB C3E HE32   SING N N 76 
EEB C4E HE41   SING N N 77 
EEB C4E HE42   SING N N 78 
EEB C4E HE43   SING N N 79 
EEB O2E HO2E   SING N N 80 
# 
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 
EEB SMILES           ACDLabs              10.04 O=P(OC1OC(C(O)C(OC(C(=O)O)CC)C1NC(=O)C)CO)(O)OP(=O)(O)OCC3OC(N2C=CC(=O)NC2=O)C(O)C3O 
EEB InChI            InChI                1.02b 
;InChI=1/C21H33N3O19P2/c1-3-9(19(31)32)39-17-13(22-8(2)26)20(41-10(6-25)15(17)29)42-45(36,37)43-44(34,35)38-7-11-14(28)16(30)18(40-11)24-5-4-12(27)23-21(24)33/h4-5,9-11,13-18,20,25,28-30H,3,6-7H2,1-2H3,(H,22,26)(H,31,32)(H,34,35)(H,36,37)(H,23,27,33)/t9-,10-,11-,13-,14-,15-,16-,17-,18-,20-/m1/s1/f/h22-23,31,34,36H
;
EEB InChIKey         InChI                1.02b DFCARJAECCPPGB-AICZEPCYDB 
EEB SMILES_CANONICAL CACTVS               3.341 CC[C@@H](O[C@H]1[C@H](O)[C@@H](CO)O[C@H](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)[C@@H]1NC(C)=O)C(O)=O 
EEB SMILES           CACTVS               3.341 CC[CH](O[CH]1[CH](O)[CH](CO)O[CH](O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O)[CH]1NC(C)=O)C(O)=O 
EEB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCC(C(=O)O)O[C@@H]1[C@H]([C@H](O[C@@H]([C@H]1O)CO)O[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)NC(=O)C 
EEB SMILES           "OpenEye OEToolkits" 1.5.0 CCC(C(=O)O)OC1C(C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)NC(=O)C 
# 
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 
EEB "SYSTEMATIC NAME" ACDLabs              10.04 
;(2R)-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}butanoic acid (non-preferred name)
;
EEB "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]oxybutanoic acid" 
# 
