data_1X9
#

_chem_comp.id                                   1X9
_chem_comp.name                                 Cerulenin
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C12 H17 N O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2013-08-27
_chem_comp.pdbx_modified_date                   2020-06-17
_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                       223.268
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    1X9
_chem_comp.pdbx_model_coordinates_details       ?
_chem_comp.pdbx_model_coordinates_missing_flag  N
_chem_comp.pdbx_ideal_coordinates_details       Corina
_chem_comp.pdbx_ideal_coordinates_missing_flag  N
_chem_comp.pdbx_model_coordinates_db_code       4LS7
_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
1X9  O1     O1     O  0  1  N  N  N  -4.048  -12.035  15.375  -1.355   1.764  -0.391  O1     1X9   1  
1X9  C1     C1     C  0  1  N  N  N  -3.292  -12.727  14.690  -2.513   1.717  -0.033  C1     1X9   2  
1X9  N      N      N  0  1  N  N  N  -3.577  -13.149  13.465  -2.911   2.408   1.053  N      1X9   3  
1X9  C2     C2     C  0  1  N  N  R  -1.957  -13.155  15.283  -3.508   0.892  -0.809  C2     1X9   4  
1X9  O2     O2     O  0  1  N  N  N  -1.121  -14.034  14.539  -4.376   0.031  -0.071  O2     1X9   5  
1X9  C3     C3     C  0  1  N  N  S  -1.689  -14.512  15.795  -3.336  -0.628  -0.796  C3     1X9   6  
1X9  "C1'"  "C1'"  C  0  1  N  N  N  -2.348  -15.867  15.531  -2.184  -1.198  -0.010  "C1'"  1X9   7  
1X9  "O1'"  "O1'"  O  0  1  N  N  N  -3.479  -16.081  15.131  -2.370  -1.640   1.099  "O1'"  1X9   8  
1X9  "C2'"  "C2'"  C  0  1  N  N  N  -1.354  -16.986  15.703  -0.801  -1.218  -0.607  "C2'"  1X9   9  
1X9  "C3'"  "C3'"  C  0  1  N  N  N  -2.085  -18.291  15.992   0.197  -1.730   0.434  "C3'"  1X9  10  
1X9  "C4'"  "C4'"  C  0  1  N  N  N  -2.243  -18.495  17.445   1.580  -1.749  -0.163  "C4'"  1X9  11  
1X9  "C5'"  "C5'"  C  0  1  N  N  N  -1.605  -19.397  18.137   2.560  -1.116   0.432  "C5'"  1X9  12  
1X9  "C6'"  "C6'"  C  0  1  N  N  N  -1.690  -19.669  19.604   3.944  -1.135  -0.165  "C6'"  1X9  13  
1X9  "C7'"  "C7'"  C  0  1  N  N  N  -0.303  -19.982  20.082   4.427   0.279  -0.359  "C7'"  1X9  14  
1X9  "C8'"  "C8'"  C  0  1  N  N  N   0.619  -20.378  19.235   5.565   0.660   0.166  "C8'"  1X9  15  
1X9  "C9'"  "C9'"  C  0  1  N  N  N   2.042  -20.715  19.551   6.048   2.075  -0.029  "C9'"  1X9  16  
1X9  H1     H1     H  0  1  N  N  N  -4.451  -12.907  13.044  -3.820   2.317   1.379  H1     1X9  17  
1X9  H2     H2     H  0  1  N  N  N  -2.918  -13.709  12.963  -2.289   2.996   1.510  H2     1X9  18  
1X9  H3     H3     H  0  1  N  N  N  -1.436  -12.352  15.824  -3.898   1.352  -1.716  H3     1X9  19  
1X9  H4     H4     H  0  1  N  N  N  -0.974  -14.539  16.630  -3.614  -1.177  -1.696  H4     1X9  20  
1X9  H5     H5     H  0  1  N  N  N  -0.765  -17.095  14.781  -0.789  -1.876  -1.476  H5     1X9  21  
1X9  H6     H6     H  0  1  N  N  N  -0.682  -16.751  16.542  -0.522  -0.209  -0.912  H6     1X9  22  
1X9  H7     H7     H  0  1  N  N  N  -3.079  -18.259  15.523   0.185  -1.072   1.303  H7     1X9  23  
1X9  H8     H8     H  0  1  N  N  N  -1.508  -19.128  15.571  -0.082  -2.739   0.738  H8     1X9  24  
1X9  H9     H9     H  0  1  N  N  N  -2.934  -17.853  17.971   1.764  -2.286  -1.082  H9     1X9  25  
1X9  H10    H10    H  0  1  N  N  N  -0.929  -20.028  17.579   2.376  -0.579   1.352  H10    1X9  26  
1X9  H11    H11    H  0  1  N  N  N  -2.078  -18.784  20.129   4.622  -1.662   0.507  H11    1X9  27  
1X9  H12    H12    H  0  1  N  N  N  -2.354  -20.526  19.790   3.917  -1.646  -1.127  H12    1X9  28  
1X9  H13    H13    H  0  1  N  N  N  -0.061  -19.881  21.130   3.835   0.978  -0.932  H13    1X9  29  
1X9  H14    H14    H  0  1  N  N  N   0.319  -20.470  18.202   6.157  -0.038   0.738  H14    1X9  30  
1X9  H15    H15    H  0  1  N  N  N   2.562  -21.013  18.629   7.005   2.204   0.476  H15    1X9  31  
1X9  H16    H16    H  0  1  N  N  N   2.540  -19.835  19.984   6.169   2.274  -1.094  H16    1X9  32  
1X9  H17    H17    H  0  1  N  N  N   2.071  -21.545  20.273   5.319   2.768   0.390  H17    1X9  33  
#   #
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
1X9  N      C1     SING  N  N   1  
1X9  O2     C2     SING  N  N   2  
1X9  O2     C3     SING  N  N   3  
1X9  C1     C2     SING  N  N   4  
1X9  C1     O1     DOUB  N  N   5  
1X9  "O1'"  "C1'"  DOUB  N  N   6  
1X9  C2     C3     SING  N  N   7  
1X9  "C1'"  "C2'"  SING  N  N   8  
1X9  "C1'"  C3     SING  N  N   9  
1X9  "C2'"  "C3'"  SING  N  N  10  
1X9  "C3'"  "C4'"  SING  N  N  11  
1X9  "C4'"  "C5'"  DOUB  N  E  12  
1X9  "C5'"  "C6'"  SING  N  N  13  
1X9  "C8'"  "C9'"  SING  N  N  14  
1X9  "C8'"  "C7'"  DOUB  N  E  15  
1X9  "C6'"  "C7'"  SING  N  N  16  
1X9  N      H1     SING  N  N  17  
1X9  N      H2     SING  N  N  18  
1X9  C2     H3     SING  N  N  19  
1X9  C3     H4     SING  N  N  20  
1X9  "C2'"  H5     SING  N  N  21  
1X9  "C2'"  H6     SING  N  N  22  
1X9  "C3'"  H7     SING  N  N  23  
1X9  "C3'"  H8     SING  N  N  24  
1X9  "C4'"  H9     SING  N  N  25  
1X9  "C5'"  H10    SING  N  N  26  
1X9  "C6'"  H11    SING  N  N  27  
1X9  "C6'"  H12    SING  N  N  28  
1X9  "C7'"  H13    SING  N  N  29  
1X9  "C8'"  H14    SING  N  N  30  
1X9  "C9'"  H15    SING  N  N  31  
1X9  "C9'"  H16    SING  N  N  32  
1X9  "C9'"  H17    SING  N  N  33  
#   #
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
1X9  SMILES            ACDLabs               12.01  "O=C(CC/C=C/C/C=C/C)C1OC1C(=O)N"  
1X9  InChI             InChI                 1.03   "InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1"  
1X9  InChIKey          InChI                 1.03   GVEZIHKRYBHEFX-NQQPLRFYSA-N  
1X9  SMILES_CANONICAL  CACTVS                3.385  "C\C=C\C/C=C/CCC(=O)[C@H]1O[C@H]1C(N)=O"  
1X9  SMILES            CACTVS                3.385  "CC=CCC=CCCC(=O)[CH]1O[CH]1C(N)=O"  
1X9  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.6  "C/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N"  
1X9  SMILES            "OpenEye OEToolkits"  1.7.6  "CC=CCC=CCCC(=O)C1C(O1)C(=O)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
1X9  "SYSTEMATIC NAME"  ACDLabs               12.01  "(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide"  
1X9  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.7.6  "(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
1X9  "Create component"  2013-08-27  RCSB  
1X9  "Modify name"       2014-03-24  RCSB  
1X9  "Initial release"   2014-04-02  RCSB  
1X9  "Modify synonyms"   2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     1X9
_pdbx_chem_comp_synonyms.name        "(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
