data_CSC
# 
_chem_comp.id                                    CSC 
_chem_comp.name                                  4-(3-ACETOXYMETHYL-2-CARBOXY-8-OXO-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2-EN-7-YLCARBAMOYL)-1-CARBOXY-BUTYL-AMMONIUM 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAD 
_chem_comp.formula                               "C16 H22 N3 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "CEPHALOSPORIN C" 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2003-07-18 
_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                        416.426 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     CSC 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1PWD 
_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 
CSC S1     S1     S 0 1 N N N 17.953 -13.276 41.289 -9.056  -1.924  -3.444 S1     CSC 1  
CSC C2     C2     C 0 1 N N N 18.473 -12.144 42.625 -9.670  -0.206  -3.395 C2     CSC 2  
CSC C3     C3     C 0 1 N N N 19.244 -10.909 42.138 -8.597  0.841   -3.107 C3     CSC 3  
CSC "C3'"  "C3'"  C 0 1 N N N 20.186 -10.406 42.980 -9.191  2.138   -2.610 "C3'"  CSC 4  
CSC C4     C4     C 0 1 N N N 18.820 -10.203 40.903 -7.272  0.615   -3.269 C4     CSC 5  
CSC "C4'"  "C4'"  C 0 1 N N N 19.421 -8.968  40.282 -6.266  1.592   -2.826 "C4'"  CSC 6  
CSC O4A    O4A    O 0 1 N N N 18.681 -8.084  39.877 -6.004  2.450   -3.830 O4A    CSC 7  
CSC O4B    O4B    O 0 1 N N N 20.743 -8.861  40.094 -5.764  1.603   -1.720 O4B    CSC 8  
CSC N5     N5     N 0 1 N N N 18.276 -10.917 39.998 -6.811  -0.550  -3.793 N5     CSC 9  
CSC C6     C6     C 0 1 N N R 17.303 -11.994 40.232 -7.647  -1.506  -4.496 C6     CSC 10 
CSC C7     C7     C 0 1 N N S 16.916 -12.537 38.844 -6.436  -2.455  -4.443 C7     CSC 11 
CSC C8     C8     C 0 1 N N N 16.541 -11.368 37.962 -5.651  -1.235  -3.895 C8     CSC 12 
CSC O9     O9     O 0 1 N N N 17.208 -10.795 37.219 -4.504  -0.997  -3.598 O9     CSC 13 
CSC N10    N10    N 0 1 N N N 18.004 -13.203 38.151 -6.479  -3.588  -3.502 N10    CSC 14 
CSC C11    C11    C 0 1 N N N 18.077 -14.567 38.174 -5.352  -4.325  -3.173 C11    CSC 15 
CSC O12    O12    O 0 1 N N N 17.176 -15.275 38.520 -4.222  -4.124  -3.614 O12    CSC 16 
CSC C13    C13    C 0 1 N N N 19.291 -15.151 37.464 -5.636  -5.439  -2.184 C13    CSC 17 
CSC C14    C14    C 0 1 N N N 20.074 -16.064 38.409 -4.386  -6.244  -1.829 C14    CSC 18 
CSC C15    C15    C 0 1 N N N 19.279 -16.769 39.546 -4.671  -7.325  -0.775 C15    CSC 19 
CSC C16    C16    C 0 1 N N R 20.070 -16.871 40.875 -3.468  -8.206  -0.417 C16    CSC 20 
CSC N17    N17    N 1 1 N N N 19.572 -17.928 41.799 -2.364  -7.350  0.105  N17    CSC 21 
CSC C18    C18    C 0 1 N N N 21.493 -17.349 40.503 -3.809  -9.291  0.582  C18    CSC 22 
CSC O19    O19    O 0 1 N N N 22.353 -16.401 40.113 -3.326  -9.389  1.702  O19    CSC 23 
CSC O20    O20    O 0 1 N N N 21.826 -18.473 40.558 -4.731  -10.162 0.097  O20    CSC 24 
CSC O1     O1     O 0 1 N N N ?      ?       ?      -10.059 2.662   -3.593 O1     CSC 25 
CSC C1     C1     C 0 1 N N N ?      ?       ?      -10.678 3.846   -3.283 C1     CSC 26 
CSC O2     O2     O 0 1 N N N ?      ?       ?      -10.541 4.473   -2.242 O2     CSC 27 
CSC C20    C20    C 0 1 N N N ?      ?       ?      -11.563 4.280   -4.413 C20    CSC 28 
CSC H11    1H1    H 0 1 N N N 17.568 -11.795 43.145 -10.434 -0.177  -2.611 H11    CSC 29 
CSC H12    2H1    H 0 1 N N N 19.156 -12.710 43.275 -10.159 0.024   -4.348 H12    CSC 30 
CSC "H3'1" "1H3'" H 0 0 N N N 20.343 -10.019 43.998 -8.396  2.848   -2.406 "H3'1" CSC 31 
CSC "H3'2" "2H3'" H 0 0 N N N 21.116 -10.595 43.537 -9.753  1.942   -1.702 "H3'2" CSC 32 
CSC H4A    H4A    H 0 1 N N N 19.197 -7.405  39.459 -5.335  3.119   -3.571 H4A    CSC 33 
CSC H6     H6     H 0 1 N N N 16.421 -11.609 40.765 -7.905  -1.180  -5.511 H6     CSC 34 
CSC H7     H7     H 0 1 N N N 16.103 -13.258 39.016 -6.087  -2.789  -5.422 H7     CSC 35 
CSC H10    H10    H 0 1 N N N 18.693 -12.669 37.662 -7.364  -3.847  -3.075 H10    CSC 36 
CSC H131   1H13   H 0 0 N N N 18.954 -15.735 36.595 -6.053  -4.990  -1.274 H131   CSC 37 
CSC H132   2H13   H 0 0 N N N 19.945 -14.328 37.139 -6.411  -6.091  -2.602 H132   CSC 38 
CSC H141   1H14   H 0 0 N N N 20.520 -16.857 37.791 -3.965  -6.703  -2.731 H141   CSC 39 
CSC H142   2H14   H 0 0 N N N 20.784 -15.401 38.925 -3.635  -5.545  -1.444 H142   CSC 40 
CSC H151   1H15   H 0 0 N N N 18.363 -16.190 39.735 -5.043  -6.842  0.137  H151   CSC 41 
CSC H152   2H15   H 0 0 N N N 19.067 -17.795 39.211 -5.483  -7.969  -1.134 H152   CSC 42 
CSC H16    H16    H 0 1 N N N 19.992 -15.890 41.367 -3.059  -8.679  -1.316 H16    CSC 43 
CSC H171   1H17   H 0 0 N N N 19.460 -18.785 41.296 -1.698  -7.130  -0.640 H171   CSC 44 
CSC H172   2H17   H 0 0 N N N 20.230 -18.060 42.540 -1.862  -7.831  0.855  H172   CSC 45 
CSC H173   3H17   H 0 0 N N N 18.691 -17.649 42.181 -2.735  -6.472  0.476  H173   CSC 46 
CSC H20    H20    H 0 1 N N N 22.736 -18.548 40.294 -4.988  -10.883 0.711  H20    CSC 47 
CSC H201   1H20   H 0 0 N N N ?      ?       ?      -12.339 3.530   -4.585 H201   CSC 48 
CSC H202   2H20   H 0 0 N N N ?      ?       ?      -10.965 4.429   -5.316 H202   CSC 49 
CSC H203   3H20   H 0 0 N N N ?      ?       ?      -12.044 5.227   -4.154 H203   CSC 50 
# 
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 
CSC S1    C2     SING N N 1  
CSC S1    C6     SING N N 2  
CSC C2    C3     SING N N 3  
CSC C2    H11    SING N N 4  
CSC C2    H12    SING N N 5  
CSC C3    "C3'"  SING N N 6  
CSC C3    C4     DOUB N N 7  
CSC "C3'" O1     SING N N 8  
CSC "C3'" "H3'1" SING N N 9  
CSC "C3'" "H3'2" SING N N 10 
CSC C4    "C4'"  SING N N 11 
CSC C4    N5     SING N N 12 
CSC "C4'" O4A    SING N N 13 
CSC "C4'" O4B    DOUB N N 14 
CSC O4A   H4A    SING N N 15 
CSC N5    C6     SING N N 16 
CSC N5    C8     SING N N 17 
CSC C6    C7     SING N N 18 
CSC C6    H6     SING N N 19 
CSC C7    C8     SING N N 20 
CSC C7    N10    SING N N 21 
CSC C7    H7     SING N N 22 
CSC C8    O9     DOUB N N 23 
CSC N10   C11    SING N N 24 
CSC N10   H10    SING N N 25 
CSC C11   O12    DOUB N N 26 
CSC C11   C13    SING N N 27 
CSC C13   C14    SING N N 28 
CSC C13   H131   SING N N 29 
CSC C13   H132   SING N N 30 
CSC C14   C15    SING N N 31 
CSC C14   H141   SING N N 32 
CSC C14   H142   SING N N 33 
CSC C15   C16    SING N N 34 
CSC C15   H151   SING N N 35 
CSC C15   H152   SING N N 36 
CSC C16   N17    SING N N 37 
CSC C16   C18    SING N N 38 
CSC C16   H16    SING N N 39 
CSC N17   H171   SING N N 40 
CSC N17   H172   SING N N 41 
CSC N17   H173   SING N N 42 
CSC C18   O19    DOUB N N 43 
CSC C18   O20    SING N N 44 
CSC O20   H20    SING N N 45 
CSC O1    C1     SING N N 46 
CSC C1    O2     DOUB N N 47 
CSC C1    C20    SING N N 48 
CSC C20   H201   SING N N 49 
CSC C20   H202   SING N N 50 
CSC C20   H203   SING N N 51 
# 
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 
CSC SMILES           ACDLabs              10.04 O=C2N1C(=C(CSC1C2NC(=O)CCCC(C(=O)O)[NH3+])COC(=O)C)C(=O)O                                                                                                                                                    
CSC InChI            InChI                1.02b InChI=1/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/p+1/t9-,11-,14-/m1/s1/fC16H22N3O8S/h17-18,23,25H/q+1 
CSC InChIKey         InChI                1.02b HOKIDJSKDBPKTQ-OOJOABRLDV                                                                                                                                                                                    
CSC SMILES_CANONICAL CACTVS               3.341 CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CCC[C@@H]([NH3+])C(O)=O)C2=O)C(O)=O                                                                                                                                     
CSC SMILES           CACTVS               3.341 CC(=O)OCC1=C(N2[CH](SC1)[CH](NC(=O)CCC[CH]([NH3+])C(O)=O)C2=O)C(O)=O                                                                                                                                         
CSC SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CCC[C@H](C(=O)O)[NH3+])SC1)C(=O)O                                                                                                                                    
CSC SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CCCC(C(=O)O)[NH3+])SC1)C(=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 
CSC "SYSTEMATIC NAME" ACDLabs              10.04 (1R)-5-({(6R,7R)-3-[(acetyloxy)methyl]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl}amino)-1-carboxy-5-oxopentan-1-aminium       
CSC "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 [(2R)-6-[[(6R,7R)-3-(acetyloxymethyl)-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]amino]-1-hydroxy-1,6-dioxo-hexan-2-yl]azanium 
# 
