data_NCC # _chem_comp.id NCC _chem_comp.name ;CYTIDINE-5'-MONOPHOSPHATE-5-N-ACETYLNEURAMINIC ACID ; _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H31 N4 O16 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2003-09-12 _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 614.451 _chem_comp.one_letter_code ? _chem_comp.three_letter_code NCC _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 1QWJ _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 NCC O3P O3P O 0 1 N N N 111.156 3.867 11.430 -1.037 -1.643 1.178 O3P NCC 1 NCC P P P 0 1 N N S 112.032 3.619 10.264 0.265 -1.111 0.396 P NCC 2 NCC O2P O2P O 0 1 N N N 111.160 3.081 9.012 1.289 -0.450 1.448 O2P NCC 3 NCC O1P O1P O 0 1 N N N 112.718 4.887 9.901 0.925 -2.244 -0.289 O1P NCC 4 NCC "O5'" "O5'" O 0 1 N N N 113.137 2.521 10.572 -0.174 -0.008 -0.690 "O5'" NCC 5 NCC "C5'" "C5'" C 0 1 N N N 112.893 1.158 11.016 -1.078 -0.652 -1.590 "C5'" NCC 6 NCC "C4'" "C4'" C 0 1 N N R 113.838 0.897 12.231 -1.536 0.347 -2.654 "C4'" NCC 7 NCC "O4'" "O4'" O 0 1 N N N 115.117 0.535 11.677 -0.406 0.803 -3.415 "O4'" NCC 8 NCC "C1'" "C1'" C 0 1 N N R 116.157 1.389 12.184 -0.867 1.020 -4.766 "C1'" NCC 9 NCC N1 N1 N 0 1 Y N N 117.199 1.760 11.184 0.256 0.992 -5.706 N1 NCC 10 NCC C6 C6 C 0 1 Y N N 116.921 1.750 9.832 0.510 2.076 -6.491 C6 NCC 11 NCC C5 C5 C 0 1 Y N N 117.920 2.080 8.874 1.551 2.039 -7.355 C5 NCC 12 NCC C4 C4 C 0 1 Y N N 119.216 2.414 9.369 2.345 0.875 -7.418 C4 NCC 13 NCC N4 N4 N 0 1 N N N 120.230 2.727 8.505 3.409 0.809 -8.288 N4 NCC 14 NCC N3 N3 N 0 1 Y N N 119.445 2.416 10.718 2.060 -0.156 -6.634 N3 NCC 15 NCC C2 C2 C 0 1 Y N N 118.473 2.089 11.631 1.035 -0.101 -5.785 C2 NCC 16 NCC O2 O2 O 0 1 N N N 118.750 2.110 12.838 0.793 -1.063 -5.075 O2 NCC 17 NCC "C2'" "C2'" C 0 1 N N R 115.481 2.590 12.882 -1.823 -0.173 -5.018 "C2'" NCC 18 NCC "O2'" "O2'" O 0 1 N N N 116.111 2.912 14.115 -2.784 0.145 -6.025 "O2'" NCC 19 NCC "C3'" "C3'" C 0 1 N N S 113.999 2.211 13.015 -2.506 -0.340 -3.635 "C3'" NCC 20 NCC "O3'" "O3'" O 0 1 N N N 113.677 1.940 14.382 -3.780 0.307 -3.625 "O3'" NCC 21 NCC C9 C9 C 0 1 N N N 110.875 4.805 7.316 1.477 -2.742 2.122 C9 NCC 22 NCC O1B O1B O 0 1 N N N 110.414 5.546 8.172 2.597 -3.130 1.491 O1B NCC 23 NCC O1A O1A O 0 1 N N N 110.982 5.204 6.051 0.589 -3.536 2.319 O1A NCC 24 NCC C10 C10 C 0 1 N N R 111.348 3.387 7.585 1.329 -1.315 2.585 C10 NCC 25 NCC O6 O6 O 0 1 N N N 110.524 2.471 6.808 0.118 -1.180 3.326 O6 NCC 26 NCC C12 C12 C 0 1 N N R 110.918 1.079 6.973 -0.076 0.207 3.590 C12 NCC 27 NCC C13 C13 C 0 1 N N R 109.955 0.211 6.139 -1.456 0.417 4.217 C13 NCC 28 NCC O7 O7 O 0 1 N N N 109.765 0.830 4.864 -1.581 -0.403 5.380 O7 NCC 29 NCC C14 C14 C 0 1 N N R 108.611 0.099 6.868 -2.538 0.036 3.205 C14 NCC 30 NCC O8 O8 O 0 1 N N N 108.797 -0.519 8.139 -2.474 0.919 2.083 O8 NCC 31 NCC C15 C15 C 0 1 N N N 107.607 -0.730 6.065 -3.915 0.147 3.864 C15 NCC 32 NCC O9 O9 O 0 1 N N N 106.530 0.122 5.658 -4.926 -0.208 2.919 O9 NCC 33 NCC C16 C16 C 0 1 N N R 112.427 0.865 6.525 1.002 0.707 4.554 C16 NCC 34 NCC N5 N5 N 0 1 N N N 112.841 -0.520 6.709 0.783 2.127 4.840 N5 NCC 35 NCC C17 C17 C 0 1 N N N 113.324 -1.166 5.506 1.157 2.640 6.029 C17 NCC 36 NCC O10 O10 O 0 1 N N N 113.389 -0.614 4.416 1.676 1.926 6.861 O10 NCC 37 NCC C18 C18 C 0 1 N N N 113.764 -2.598 5.632 0.932 4.101 6.324 C18 NCC 38 NCC C19 C19 C 0 1 N N S 113.346 1.799 7.366 2.379 0.521 3.905 C19 NCC 39 NCC O4 O4 O 0 1 N N N 114.725 1.648 6.978 3.401 0.845 4.849 O4 NCC 40 NCC C20 C20 C 0 1 N N N 112.861 3.253 7.144 2.521 -0.940 3.468 C20 NCC 41 NCC H3P H3P H 0 1 N N N 111.668 4.182 12.165 -1.515 -0.862 1.488 H3P NCC 42 NCC "H5'1" "1H5'" H 0 0 N N N 111.820 0.957 11.244 -0.575 -1.490 -2.072 "H5'1" NCC 43 NCC "H5'2" "2H5'" H 0 0 N N N 113.008 0.405 10.201 -1.943 -1.016 -1.037 "H5'2" NCC 44 NCC "H4'" "H4'" H 0 1 N N N 113.438 0.103 12.904 -2.029 1.194 -2.178 "H4'" NCC 45 NCC "H1'" "H1'" H 0 1 N N N 116.761 0.823 12.931 -1.405 1.965 -4.841 "H1'" NCC 46 NCC H6 H6 H 0 1 N N N 115.899 1.478 9.516 -0.112 2.956 -6.425 H6 NCC 47 NCC H5 H5 H 0 1 N N N 117.699 2.077 7.793 1.771 2.887 -7.987 H5 NCC 48 NCC HN41 1HN4 H 0 0 N N N 121.156 2.965 8.858 3.953 0.007 -8.329 HN41 NCC 49 NCC HN42 2HN4 H 0 0 N N N 119.913 3.485 7.901 3.615 1.565 -8.860 HN42 NCC 50 NCC "H2'" "H2'" H 0 1 N N N 115.580 3.529 12.290 -1.263 -1.069 -5.287 "H2'" NCC 51 NCC H1 H1 H 0 1 N N N 115.695 3.650 14.544 -3.345 -0.634 -6.134 H1 NCC 52 NCC "H3'" "H3'" H 0 1 N N N 113.343 3.033 12.644 -2.614 -1.396 -3.387 "H3'" NCC 53 NCC H2 H2 H 0 1 N N N 113.776 2.751 14.866 -4.319 -0.128 -4.299 H2 NCC 54 NCC H1B H1B H 0 1 N N N 110.337 5.261 9.075 2.692 -4.045 1.195 H1B NCC 55 NCC H12 H12 H 0 1 N N N 110.855 0.783 8.046 -0.013 0.766 2.657 H12 NCC 56 NCC H13 H13 H 0 1 N N N 110.380 -0.810 6.000 -1.572 1.464 4.496 H13 NCC 57 NCC HO7 HO7 H 0 1 N N N 109.171 0.295 4.350 -1.472 -1.319 5.088 HO7 NCC 58 NCC H14 H14 H 0 1 N N N 108.209 1.131 6.992 -2.378 -0.988 2.869 H14 NCC 59 NCC HO8 HO8 H 0 1 N N N 107.964 -0.588 8.590 -2.621 1.813 2.423 HO8 NCC 60 NCC H151 1H15 H 0 0 N N N 108.081 -1.258 5.205 -3.963 -0.526 4.719 H151 NCC 61 NCC H152 2H15 H 0 0 N N N 107.253 -1.628 6.622 -4.075 1.172 4.199 H152 NCC 62 NCC HO9 HO9 H 0 1 N N N 105.906 -0.392 5.159 -5.775 -0.124 3.373 HO9 NCC 63 NCC H16 H16 H 0 1 N N N 112.513 1.111 5.441 0.956 0.136 5.481 H16 NCC 64 NCC HN5 HN5 H 0 1 N N N 112.796 -0.999 7.608 0.368 2.698 4.175 HN5 NCC 65 NCC H181 1H18 H 0 0 N N N 114.135 -3.095 4.705 1.296 4.329 7.326 H181 NCC 66 NCC H182 2H18 H 0 0 N N N 114.533 -2.681 6.434 1.470 4.706 5.595 H182 NCC 67 NCC H183 3H18 H 0 0 N N N 112.938 -3.203 6.074 -0.133 4.323 6.265 H183 NCC 68 NCC H19 H19 H 0 1 N N N 113.284 1.533 8.447 2.464 1.173 3.036 H19 NCC 69 NCC HO4 HO4 H 0 1 N N N 115.285 2.217 7.491 4.248 0.714 4.400 HO4 NCC 70 NCC H201 1H20 H 0 0 N N N 113.023 3.593 6.094 3.446 -1.063 2.904 H201 NCC 71 NCC H202 2H20 H 0 0 N N N 113.514 3.995 7.657 2.541 -1.583 4.347 H202 NCC 72 # 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 NCC O3P P SING N N 1 NCC O3P H3P SING N N 2 NCC P O2P SING N N 3 NCC P O1P DOUB N N 4 NCC P "O5'" SING N N 5 NCC O2P C10 SING N N 6 NCC "O5'" "C5'" SING N N 7 NCC "C5'" "C4'" SING N N 8 NCC "C5'" "H5'1" SING N N 9 NCC "C5'" "H5'2" SING N N 10 NCC "C4'" "O4'" SING N N 11 NCC "C4'" "C3'" SING N N 12 NCC "C4'" "H4'" SING N N 13 NCC "O4'" "C1'" SING N N 14 NCC "C1'" N1 SING N N 15 NCC "C1'" "C2'" SING N N 16 NCC "C1'" "H1'" SING N N 17 NCC N1 C6 SING Y N 18 NCC N1 C2 SING Y N 19 NCC C6 C5 DOUB Y N 20 NCC C6 H6 SING N N 21 NCC C5 C4 SING Y N 22 NCC C5 H5 SING N N 23 NCC C4 N4 SING N N 24 NCC C4 N3 DOUB Y N 25 NCC N4 HN41 SING N N 26 NCC N4 HN42 SING N N 27 NCC N3 C2 SING Y N 28 NCC C2 O2 DOUB N N 29 NCC "C2'" "O2'" SING N N 30 NCC "C2'" "C3'" SING N N 31 NCC "C2'" "H2'" SING N N 32 NCC "O2'" H1 SING N N 33 NCC "C3'" "O3'" SING N N 34 NCC "C3'" "H3'" SING N N 35 NCC "O3'" H2 SING N N 36 NCC C9 O1B SING N N 37 NCC C9 O1A DOUB N N 38 NCC C9 C10 SING N N 39 NCC O1B H1B SING N N 40 NCC C10 O6 SING N N 41 NCC C10 C20 SING N N 42 NCC O6 C12 SING N N 43 NCC C12 C13 SING N N 44 NCC C12 C16 SING N N 45 NCC C12 H12 SING N N 46 NCC C13 O7 SING N N 47 NCC C13 C14 SING N N 48 NCC C13 H13 SING N N 49 NCC O7 HO7 SING N N 50 NCC C14 O8 SING N N 51 NCC C14 C15 SING N N 52 NCC C14 H14 SING N N 53 NCC O8 HO8 SING N N 54 NCC C15 O9 SING N N 55 NCC C15 H151 SING N N 56 NCC C15 H152 SING N N 57 NCC O9 HO9 SING N N 58 NCC C16 N5 SING N N 59 NCC C16 C19 SING N N 60 NCC C16 H16 SING N N 61 NCC N5 C17 SING N N 62 NCC N5 HN5 SING N N 63 NCC C17 O10 DOUB N N 64 NCC C17 C18 SING N N 65 NCC C18 H181 SING N N 66 NCC C18 H182 SING N N 67 NCC C18 H183 SING N N 68 NCC C19 O4 SING N N 69 NCC C19 C20 SING N N 70 NCC C19 H19 SING N N 71 NCC O4 HO4 SING N N 72 NCC C20 H201 SING N N 73 NCC C20 H202 SING N N 74 # 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 NCC SMILES ACDLabs 10.04 "O=C(NC1C(O)CC(OC1C(O)C(O)CO)(OP(=O)(O)OCC3OC(N2C(=O)N=C(N)C=C2)C(O)C3O)C(=O)O)C" NCC SMILES_CANONICAL CACTVS 3.341 "CC(=O)N[C@@H]1[C@@H](O)C[C@@](O[C@H]1[C@H](O)[C@H](O)CO)(O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=NC3=O)N)C(O)=O" NCC SMILES CACTVS 3.341 "CC(=O)N[CH]1[CH](O)C[C](O[CH]1[CH](O)[CH](O)CO)(O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=NC3=O)N)C(O)=O" NCC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O[P@@](=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=NC3=O)N)O)O)O" NCC SMILES "OpenEye OEToolkits" 1.5.0 "CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=NC3=O)N)O)O)O" NCC InChI InChI 1.03 ;InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1 ; NCC InChIKey InChI 1.03 TXCIAUNLDRJGJZ-BILDWYJOSA-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 NCC "SYSTEMATIC NAME" ACDLabs 10.04 ;(2R,4S,5R,6R)-5-(acetylamino)-2-{[(S)-{[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylic acid (non-preferred name) ; NCC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic 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 NCC "Create component" 2003-09-12 RCSB NCC "Modify descriptor" 2011-06-04 RCSB #