data_CSF
# 
_chem_comp.id                                    CSF 
_chem_comp.name                                  
;CYTIDINE-5'-MONOPHOSPHATE-3-FLUORO-N-ACETYL-NEURAMINIC ACID
;
_chem_comp.type                                  "RNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C20 H30 F N4 O16 P" 
_chem_comp.mon_nstd_parent_comp_id               C 
_chem_comp.pdbx_synonyms                         CMP-3FNEUAC 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2003-12-04 
_chem_comp.pdbx_modified_date                    2009-01-07 
_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                        632.442 
_chem_comp.one_letter_code                       C 
_chem_comp.three_letter_code                     CSF 
_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        ? 
_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 
CSF C5A    C5A  C 0 1 N N R 22.128 -5.514 11.468 -0.501 -1.002 4.162  C5A    CSF 1  
CSF C4A    C4A  C 0 1 N N R 22.005 -4.016 11.206 -1.862 -1.356 3.552  C4A    CSF 2  
CSF C2A    C2A  C 0 1 N N S 20.752 -3.803 13.492 -1.574 0.675  2.135  C2A    CSF 3  
CSF O6A    O6A  O 0 1 N N N 21.531 -4.968 13.845 -0.384 1.021  2.841  O6A    CSF 4  
CSF C6A    C6A  C 0 1 N N R 22.472 -5.670 12.982 0.305  -0.188 3.148  C6A    CSF 5  
CSF C3A    C3A  C 0 1 N N R 20.939 -3.255 12.057 -2.533 -0.066 3.068  C3A    CSF 6  
CSF O4A    O4A  O 0 1 N N N 21.682 -3.890 9.804  -2.681 -1.986 4.539  O4A    CSF 7  
CSF N5A    N5A  N 0 1 N N N 23.114 -6.222 10.755 0.223  -2.232 4.491  N5A    CSF 8  
CSF C7A    C7A  C 0 1 N N R 22.363 -7.031 13.677 1.678  0.143  3.736  C7A    CSF 9  
CSF C8A    C8A  C 0 1 N N R 22.653 -7.190 15.150 1.499  0.954  5.022  C8A    CSF 10 
CSF C9A    C9A  C 0 1 N N N 22.735 -8.635 15.676 2.863  1.175  5.679  C9A    CSF 11 
CSF O9A    O9A  O 0 1 N N N 22.997 -8.659 17.056 2.696  1.932  6.880  O9A    CSF 12 
CSF O8A    O8A  O 0 1 N N N 23.915 -6.633 15.565 0.911  2.218  4.709  O8A    CSF 13 
CSF O7A    O7A  O 0 1 N N N 21.056 -7.596 13.365 2.375  -1.068 4.031  O7A    CSF 14 
CSF C1A    C1A  C 0 1 N N N 19.771 -3.135 14.370 -2.238 1.929  1.627  C1A    CSF 15 
CSF OBA    OBA  O 0 1 N N N 19.340 -1.877 14.094 -3.378 1.847  0.923  OBA    CSF 16 
CSF OAA    OAA  O 0 1 N N N 19.343 -3.747 15.302 -1.744 3.009  1.854  OAA    CSF 17 
CSF O1A    O1A  O 0 1 N N N 21.820 -2.911 13.997 -1.242 -0.165 1.028  O1A    CSF 18 
CSF O2A    O2A  O 0 1 N N N 24.350 -2.909 13.223 0.883  1.189  0.898  O2A    CSF 19 
CSF N1     N1   N 0 1 N N N 24.519 2.408  13.595 0.152  -0.817 -6.180 N1     CSF 20 
CSF C2     C2   C 0 1 N N N 24.449 3.495  12.635 -0.714 0.211  -6.188 C2     CSF 21 
CSF N3     N3   N 0 1 N N N 25.500 3.557  11.621 -1.710 0.264  -7.071 N3     CSF 22 
CSF C4     C4   C 0 1 N N N 26.530 2.614  11.565 -1.880 -0.705 -7.959 C4     CSF 23 
CSF C5     C5   C 0 1 N N N 26.607 1.476  12.559 -0.992 -1.801 -7.973 C5     CSF 24 
CSF C6     C6   C 0 1 N N N 25.593 1.441  13.517 0.018  -1.837 -7.073 C6     CSF 25 
CSF "C3'"  C3*  C 0 1 N N S 21.794 0.562  14.634 2.719  0.529  -3.879 "C3'"  CSF 26 
CSF "C2'"  C2*  C 0 1 N N R 21.999 2.000  14.241 2.100  0.442  -5.299 "C2'"  CSF 27 
CSF "C1'"  C1*  C 0 1 N N R 23.411 2.334  14.684 1.241  -0.844 -5.201 "C1'"  CSF 28 
CSF "O4'"  O4*  O 0 1 N N N 23.748 1.360  15.703 0.718  -0.798 -3.856 "O4'"  CSF 29 
CSF "C4'"  C4*  C 0 1 N N R 22.643 0.450  15.913 1.779  -0.327 -3.008 "C4'"  CSF 30 
CSF PA     PA   P 0 1 N N R 23.416 -2.715 14.360 -0.243 0.675  0.087  PA     CSF 31 
CSF "O5'"  O5*  O 0 1 N N N 23.955 -1.364 14.939 0.325  -0.277 -1.078 "O5'"  CSF 32 
CSF "C5'"  C5*  C 0 1 N N N 23.226 -0.887 16.093 1.201  0.523  -1.875 "C5'"  CSF 33 
CSF "O3'"  O3*  O 0 1 N N N 20.431 0.286  14.998 4.042  -0.009 -3.877 "O3'"  CSF 34 
CSF "O2'"  O2*  O 0 1 N N N 21.135 2.905  14.947 3.118  0.301  -6.290 "O2'"  CSF 35 
CSF N4     N4   N 0 1 N N N 27.437 2.726  10.635 -2.915 -0.643 -8.863 N4     CSF 36 
CSF O2     O2   O 0 1 N N N 23.521 4.387  12.645 -0.579 1.116  -5.381 O2     CSF 37 
CSF O3A    O3A  O 0 1 N N N 23.812 -3.618 15.332 -1.038 1.911  -0.569 O3A    CSF 38 
CSF C10    C10  C 0 1 N N N 23.054 -7.477 10.270 0.081  -2.792 5.709  C10    CSF 39 
CSF O10    O10  O 0 1 N N N 22.051 -8.177 10.425 -0.646 -2.278 6.532  O10    CSF 40 
CSF C11    C11  C 0 1 N N N 24.261 -8.009 9.528  0.826  -4.057 6.048  C11    CSF 41 
CSF F3A    F3A  F 0 1 N N N 19.690 -3.497 11.573 -2.839 0.743  4.168  F3A    CSF 42 
CSF H5A    H5A  H 0 1 N N N 21.159 -5.951 11.131 -0.649 -0.412 5.067  H5A    CSF 43 
CSF H4A    H4A  H 0 1 N N N 22.968 -3.540 11.502 -1.720 -2.032 2.709  H4A    CSF 44 
CSF H6A    H6A  H 0 1 N N N 23.528 -5.324 12.896 0.433  -0.773 2.237  H6A    CSF 45 
CSF H3A    H3A  H 0 1 N N N 21.306 -2.202 12.029 -3.449 -0.311 2.530  H3A    CSF 46 
CSF H4     H4   H 0 1 N N N 21.605 -2.957 9.640  -3.524 -2.191 4.113  H4     CSF 47 
CSF H3     H3   H 0 1 N N N 24.001 -5.757 10.561 0.805  -2.643 3.833  H3     CSF 48 
CSF H7A    H7A  H 0 1 N N N 23.237 -7.576 13.251 2.251  0.726  3.016  H7A    CSF 49 
CSF H8A    H8A  H 0 1 N N N 21.767 -6.654 15.565 0.849  0.410  5.707  H8A    CSF 50 
CSF H9A1   1H9A H 0 0 N N N 21.817 -9.216 15.422 3.513  1.718  4.994  H9A1   CSF 51 
CSF H9A2   2H9A H 0 0 N N N 23.481 -9.236 15.106 3.311  0.210  5.918  H9A2   CSF 52 
CSF H9A    H9A  H 0 1 N N N 23.047 -9.550 17.380 3.576  2.048  7.262  H9A    CSF 53 
CSF H2     H2   H 0 1 N N N 24.097 -6.733 16.491 1.516  2.666  4.102  H2     CSF 54 
CSF H1     H1   H 0 1 N N N 20.988 -8.439 13.796 1.962  -1.444 4.820  H1     CSF 55 
CSF HBA    HBA  H 0 1 N N N 18.708 -1.447 14.659 -3.804 2.652  0.598  HBA    CSF 56 
CSF H7     H7   H 0 1 N N N 27.382 0.692  12.584 -1.117 -2.599 -8.690 H7     CSF 57 
CSF H6     H6   H 0 1 N N N 25.642 0.613  14.244 0.711  -2.665 -7.064 H6     CSF 58 
CSF "H3'"  H3*  H 0 1 N N N 22.056 -0.134 13.804 2.728  1.561  -3.529 "H3'"  CSF 59 
CSF "H2'"  H2*  H 0 1 N N N 21.797 2.110  13.149 1.475  1.311  -5.506 "H2'"  CSF 60 
CSF "H1'"  H1*  H 0 1 N N N 23.393 3.388  15.045 1.860  -1.730 -5.341 "H1'"  CSF 61 
CSF "H4'"  H4*  H 0 1 N N N 22.007 0.667  16.803 2.326  -1.173 -2.594 "H4'"  CSF 62 
CSF "H5'"  1H5* H 0 1 N N N 23.868 -0.916 17.003 0.645  1.360  -2.297 "H5'"  CSF 63 
CSF "H5''" 2H5* H 0 0 N N N 22.442 -1.620 16.393 2.013  0.901  -1.255 "H5''" CSF 64 
CSF "HO3'" H3T  H 0 0 N Y N 20.301 -0.621 15.246 4.565  0.531  -4.484 "HO3'" CSF 65 
CSF H8     H8   H 0 1 N N N 21.264 3.812  14.698 3.614  1.131  -6.302 H8     CSF 66 
CSF H41    1H4  H 0 1 N N N 28.188 2.037  10.594 -3.524 0.111  -8.851 H41    CSF 67 
CSF H42    2H4  H 0 1 N N N 27.847 3.658  10.686 -3.037 -1.354 -9.511 H42    CSF 68 
CSF H5     H5   H 0 1 N N N 24.731 -3.505 15.541 -1.762 1.534  -1.088 H5     CSF 69 
CSF H111   1H11 H 0 0 N N N 24.211 -9.048 9.126  0.587  -4.358 7.068  H111   CSF 70 
CSF H112   2H11 H 0 0 N N N 24.519 -7.308 8.699  0.532  -4.848 5.358  H112   CSF 71 
CSF H113   3H11 H 0 0 N N N 25.162 -7.910 10.177 1.899  -3.881 5.962  H113   CSF 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 
CSF C5A   C4A    SING N N 1  
CSF C5A   C6A    SING N N 2  
CSF C5A   N5A    SING N N 3  
CSF C5A   H5A    SING N N 4  
CSF C4A   C3A    SING N N 5  
CSF C4A   O4A    SING N N 6  
CSF C4A   H4A    SING N N 7  
CSF C2A   O6A    SING N N 8  
CSF C2A   C3A    SING N N 9  
CSF C2A   C1A    SING N N 10 
CSF C2A   O1A    SING N N 11 
CSF O6A   C6A    SING N N 12 
CSF C6A   C7A    SING N N 13 
CSF C6A   H6A    SING N N 14 
CSF C3A   F3A    SING N N 15 
CSF C3A   H3A    SING N N 16 
CSF O4A   H4     SING N N 17 
CSF N5A   C10    SING N N 18 
CSF N5A   H3     SING N N 19 
CSF C7A   C8A    SING N N 20 
CSF C7A   O7A    SING N N 21 
CSF C7A   H7A    SING N N 22 
CSF C8A   C9A    SING N N 23 
CSF C8A   O8A    SING N N 24 
CSF C8A   H8A    SING N N 25 
CSF C9A   O9A    SING N N 26 
CSF C9A   H9A1   SING N N 27 
CSF C9A   H9A2   SING N N 28 
CSF O9A   H9A    SING N N 29 
CSF O8A   H2     SING N N 30 
CSF O7A   H1     SING N N 31 
CSF C1A   OBA    SING N N 32 
CSF C1A   OAA    DOUB N N 33 
CSF OBA   HBA    SING N N 34 
CSF O1A   PA     SING N N 35 
CSF O2A   PA     DOUB N N 36 
CSF N1    C2     SING N N 37 
CSF N1    C6     SING N N 38 
CSF N1    "C1'"  SING N N 39 
CSF C2    N3     SING N N 40 
CSF C2    O2     DOUB N N 41 
CSF N3    C4     DOUB N N 42 
CSF C4    C5     SING N N 43 
CSF C4    N4     SING N N 44 
CSF C5    C6     DOUB N N 45 
CSF C5    H7     SING N N 46 
CSF C6    H6     SING N N 47 
CSF "C3'" "C2'"  SING N N 48 
CSF "C3'" "C4'"  SING N N 49 
CSF "C3'" "O3'"  SING N N 50 
CSF "C3'" "H3'"  SING N N 51 
CSF "C2'" "C1'"  SING N N 52 
CSF "C2'" "O2'"  SING N N 53 
CSF "C2'" "H2'"  SING N N 54 
CSF "C1'" "O4'"  SING N N 55 
CSF "C1'" "H1'"  SING N N 56 
CSF "O4'" "C4'"  SING N N 57 
CSF "C4'" "C5'"  SING N N 58 
CSF "C4'" "H4'"  SING N N 59 
CSF PA    "O5'"  SING N N 60 
CSF PA    O3A    SING N N 61 
CSF "O5'" "C5'"  SING N N 62 
CSF "C5'" "H5'"  SING N N 63 
CSF "C5'" "H5''" SING N N 64 
CSF "O3'" "HO3'" SING N N 65 
CSF "O2'" H8     SING N N 66 
CSF N4    H41    SING N N 67 
CSF N4    H42    SING N N 68 
CSF O3A   H5     SING N N 69 
CSF C10   O10    DOUB N N 70 
CSF C10   C11    SING N N 71 
CSF C11   H111   SING N N 72 
CSF C11   H112   SING N N 73 
CSF C11   H113   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 
CSF SMILES           ACDLabs              10.04 "FC3C(O)C(NC(=O)C)C(OC3(OP(=O)(O)OCC2OC(N1C(=O)N=C(N)C=C1)C(O)C2O)C(=O)O)C(O)C(O)CO" 
CSF InChI            InChI                1.02b 
;InChI=1/C20H30FN4O16P/c1-6(27)23-10-13(31)16(21)20(18(33)34,40-15(10)11(29)7(28)4-26)41-42(36,37)38-5-8-12(30)14(32)17(39-8)25-3-2-9(22)24-19(25)35/h2-3,7-8,10-17,26,28-32H,4-5H2,1H3,(H,23,27)(H,33,34)(H,36,37)(H2,22,24,35)/t7-,8-,10-,11-,12-,13-,14-,15-,16-,17-,20-/m1/s1/f/h23,33,36H,22H2
;
CSF InChIKey         InChI                1.02b HNJLGUNKGJTPBF-NMBZVVOODT 
CSF SMILES_CANONICAL CACTVS               3.341 "CC(=O)N[C@@H]1[C@@H](O)[C@@H](F)[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" 
CSF SMILES           CACTVS               3.341 "CC(=O)N[CH]1[CH](O)[CH](F)[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" 
CSF SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "CC(=O)N[C@@H]1[C@H]([C@H](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)F)O" 
CSF SMILES           "OpenEye OEToolkits" 1.5.0 "CC(=O)NC1C(C(C(OC1C(C(CO)O)O)(C(=O)O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=NC3=O)N)O)O)F)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 
CSF "SYSTEMATIC NAME" ACDLabs              10.04 
;(2S,3R,4R,5R,6R)-5-(acetylamino)-2-{[(R)-{[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-3-fluoro-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)
;
CSF "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
"(3R,4R,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-3-fluoro-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid" 
# 
