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 2011-06-04 _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 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" EEB InChI InChI 1.03 ;InChI=1S/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 ; EEB InChIKey InChI 1.03 DFCARJAECCPPGB-LHYXAPFASA-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 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" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site EEB "Create component" 1999-07-08 RCSB EEB "Modify descriptor" 2011-06-04 RCSB #