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                    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                        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 InChI            InChI                1.02b 
;InChI=1/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/f/h22,32,35H,21H2
;
NCC InChIKey         InChI                1.02b TXCIAUNLDRJGJZ-VBOXYKEVDH 
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 
# 
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" 
# 
