data_CN5
#

_chem_comp.id                                   CN5
_chem_comp.name                                 "(5S,11R)-5,8,11-trihydroxy-5,11-dioxido-17-oxo-4,6,10,12,16-pentaoxa-5,11-diphosphaoctadec-1-yl pentadecanoate"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C26 H52 O13 P2"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        CARDIOLIPIN
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2008-04-28
_chem_comp.pdbx_modified_date                   2021-03-01
_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                       634.631
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    CN5
_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       3CX5
_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
CN5  P       P       P  0  1  N  N  S  23.877   7.767  43.324    2.491  -2.749  -0.111  P       CN5   1  
CN5  O11     O11     O  0  1  N  N  N  24.783   6.460  43.932    1.165  -1.859   0.095  O11     CN5   2  
CN5  O12     O12     O  0  1  N  N  N  24.946   8.732  42.624    2.481  -3.975   0.932  O12     CN5   3  
CN5  O13     O13     O  0  1  N  N  N  23.141   8.422  44.665    3.794  -1.838   0.143  O13     CN5   4  
CN5  O14     O14     O  0  1  N  N  N  22.672   7.270  42.336    2.521  -3.278  -1.493  O14     CN5   5  
CN5  C1      C1      C  0  1  N  N  N  24.027   5.700  44.942   -0.151  -2.352  -0.161  C1      CN5   6  
CN5  C2      C2      C  0  1  N  N  N  24.187   4.390  44.283   -1.174  -1.254   0.135  C2      CN5   7  
CN5  C3      C3      C  0  1  N  N  N  22.865   3.682  44.452   -2.584  -1.782  -0.139  C3      CN5   8  
CN5  O31     O31     O  0  1  N  N  N  23.001   2.443  43.834   -3.554  -0.740   0.142  O31     CN5   9  
CN5  O32     O32     O  0  1  N  N  N  21.429   1.135  44.936   -5.158  -2.145  -0.438  O32     CN5  10  
CN5  C31     C31     C  0  1  N  N  N  21.843   1.710  43.934   -4.848  -1.044  -0.049  C31     CN5  11  
CN5  C32     C32     C  0  1  N  N  N  21.046   1.656  42.594   -5.912  -0.012   0.222  C32     CN5  12  
CN5  C33     C33     C  0  1  N  N  N  19.954   0.580  42.309   -7.289  -0.611  -0.073  C33     CN5  13  
CN5  C34     C34     C  0  1  N  N  N  18.651   1.063  42.831   -8.370   0.437   0.202  C34     CN5  14  
CN5  C35     C35     C  0  1  N  N  N  17.401   0.387  42.219   -9.747  -0.162  -0.093  C35     CN5  15  
CN5  C36     C36     C  0  1  N  N  N  16.006   0.333  42.890  -10.828   0.886   0.182  C36     CN5  16  
CN5  C37     C37     C  0  1  N  N  N  14.979  -0.278  41.872  -12.205   0.287  -0.113  C37     CN5  17  
CN5  C38     C38     C  0  1  N  N  N  14.954  -1.834  42.041  -13.285   1.335   0.162  C38     CN5  18  
CN5  C39     C39     C  0  1  N  N  N  14.384  -2.642  40.829  -14.662   0.736  -0.133  C39     CN5  19  
CN5  C3A     C3A     C  0  1  N  N  N  13.109  -3.478  41.112  -15.743   1.784   0.142  C3A     CN5  20  
CN5  C3B     C3B     C  0  1  N  N  N  11.787  -2.703  40.876  -17.120   1.185  -0.153  C3B     CN5  21  
CN5  C3C     C3C     C  0  1  N  N  N  11.081  -3.000  39.605  -18.201   2.233   0.122  C3C     CN5  22  
CN5  C3D     C3D     C  0  1  N  N  N  11.008  -1.834  38.588  -19.578   1.634  -0.173  C3D     CN5  23  
CN5  C3E     C3E     C  0  1  N  N  N  11.899  -1.708  37.326  -20.659   2.681   0.102  C3E     CN5  24  
CN5  C3F     C3F     C  0  1  N  N  N  11.275  -0.817  36.205  -22.036   2.083  -0.192  C3F     CN5  25  
CN5  "P'"    "P'"    P  0  1  N  N  R  24.714   8.400  50.241   10.037  -0.713  -0.129  "P'"    CN5  26  
CN5  "O1'"   "O1'"   O  0  1  N  N  N  23.498   7.334  49.806   10.735   0.723   0.072  "O1'"   CN5  27  
CN5  "O2'"   "O2'"   O  0  1  N  N  N  23.918   9.648  50.878   10.271  -1.187  -1.512  "O2'"   CN5  28  
CN5  "O3'"   "O3'"   O  0  1  N  N  N  25.524   8.755  48.880    8.453  -0.581   0.132  "O3'"   CN5  29  
CN5  "O4'"   "O4'"   O  0  1  N  N  N  25.828   7.775  51.275   10.666  -1.767   0.913  "O4'"   CN5  30  
CN5  "C1'"   "C1'"   C  0  1  N  N  N  24.273   6.243  49.251   12.120   0.959  -0.191  "C1'"   CN5  31  
CN5  "C2'"   "C2'"   C  0  1  N  N  N  23.838   4.966  48.681   12.453   2.423   0.102  "C2'"   CN5  32  
CN5  "C3'"   "C3'"   C  0  1  N  N  N  24.822   4.143  49.287   13.936   2.675  -0.178  "C3'"   CN5  33  
CN5  O41     O41     O  0  1  N  N  N  24.567   2.800  48.866   14.252   4.065   0.099  O41     CN5  34  
CN5  O42     O42     O  0  1  N  N  N  25.646   3.252  46.785   16.342   3.656  -0.489  O42     CN5  35  
CN5  C41     C41     C  0  1  N  N  N  25.322   2.476  47.729   15.522   4.452  -0.098  C41     CN5  36  
CN5  C42     C42     C  0  1  N  N  N  25.759   0.976  47.710   15.924   5.880   0.170  C42     CN5  37  
CN5  CA      CA      C  0  1  N  N  N  25.131   9.435  47.830    7.539  -1.661  -0.069  CA      CN5  38  
CN5  CB      CB      C  0  1  N  N  R  24.772   8.555  46.602    6.121  -1.197   0.270  CB      CN5  39  
CN5  OA      OA      O  0  1  N  N  N  25.933   8.376  45.648    6.041  -0.889   1.663  OA      CN5  40  
CN5  CC      CC      C  0  1  N  N  N  23.531   9.195  45.823    5.127  -2.311  -0.063  CC      CN5  41  
CN5  HO12    HO12    H  0  0  N  N  N  24.667   8.923  41.736    2.462  -3.702   1.860  HO12    CN5  42  
CN5  H1      H1      H  0  1  N  N  N  24.446   5.752  45.958   -0.231  -2.651  -1.207  H1      CN5  43  
CN5  H1A     H1A     H  0  1  N  N  N  23.000   6.032  45.156   -0.347  -3.213   0.478  H1A     CN5  44  
CN5  H2      H2      H  0  1  N  N  N  24.427   4.517  43.217   -1.095  -0.956   1.180  H2      CN5  45  
CN5  H2A     H2A     H  0  1  N  N  N  25.013   3.814  44.725   -0.978  -0.393  -0.504  H2A     CN5  46  
CN5  H3      H3      H  0  1  N  N  N  22.629   3.557  45.519   -2.663  -2.080  -1.184  H3      CN5  47  
CN5  H3A     H3A     H  0  1  N  N  N  22.044   4.261  44.004   -2.780  -2.643   0.501  H3A     CN5  48  
CN5  H32     H32     H  0  1  N  N  N  20.526   2.623  42.526   -5.865   0.293   1.268  H32     CN5  49  
CN5  H32A    H32A    H  0  0  N  N  N  21.829   1.392  41.868   -5.749   0.855  -0.417  H32A    CN5  50  
CN5  H33     H33     H  0  1  N  N  N  19.877   0.410  41.225   -7.336  -0.916  -1.118  H33     CN5  51  
CN5  H33A    H33A    H  0  0  N  N  N  20.225  -0.364  42.804   -7.453  -1.478   0.567  H33A    CN5  52  
CN5  H34     H34     H  0  1  N  N  N  18.636   0.871  43.914   -8.323   0.742   1.248  H34     CN5  53  
CN5  H34A    H34A    H  0  0  N  N  N  18.588   2.128  42.561   -8.206   1.304  -0.437  H34A    CN5  54  
CN5  H35     H35     H  0  1  N  N  N  17.233   0.920  41.271   -9.794  -0.467  -1.138  H35     CN5  55  
CN5  H35A    H35A    H  0  0  N  N  N  17.694  -0.672  42.258   -9.911  -1.029   0.547  H35A    CN5  56  
CN5  H36     H36     H  0  1  N  N  N  16.052  -0.295  43.792  -10.781   1.191   1.228  H36     CN5  57  
CN5  H36A    H36A    H  0  0  N  N  N  15.690   1.347  43.177  -10.664   1.753  -0.457  H36A    CN5  58  
CN5  H37     H37     H  0  1  N  N  N  13.977   0.131  42.069  -12.252  -0.018  -1.158  H37     CN5  59  
CN5  H37A    H37A    H  0  0  N  N  N  15.278  -0.022  40.845  -12.368  -0.580   0.527  H37A    CN5  60  
CN5  H38     H38     H  0  1  N  N  N  15.991  -2.165  42.198  -13.238   1.640   1.208  H38     CN5  61  
CN5  H38A    H38A    H  0  0  N  N  N  14.277  -2.036  42.884  -13.122   2.202  -0.477  H38A    CN5  62  
CN5  H39     H39     H  0  1  N  N  N  14.134  -1.918  40.040  -14.710   0.431  -1.178  H39     CN5  63  
CN5  H39A    H39A    H  0  0  N  N  N  15.165  -3.367  40.556  -14.826  -0.131   0.507  H39A    CN5  64  
CN5  H3AA    H3AA    H  0  0  N  N  N  13.117  -4.350  40.441  -15.696   2.089   1.188  H3AA    CN5  65  
CN5  H3AB    H3AB    H  0  0  N  N  N  13.135  -3.756  42.176  -15.580   2.651  -0.497  H3AB    CN5  66  
CN5  H3B     H3B     H  0  1  N  N  N  11.104  -2.959  41.699  -17.167   0.880  -1.198  H3B     CN5  67  
CN5  H3BA    H3BA    H  0  0  N  N  N  12.065  -1.640  40.826  -17.284   0.318   0.487  H3BA    CN5  68  
CN5  H3C     H3C     H  0  1  N  N  N  11.614  -3.829  39.118  -18.154   2.538   1.168  H3C     CN5  69  
CN5  H3CA    H3CA    H  0  0  N  N  N  10.041  -3.226  39.882  -18.037   3.100  -0.517  H3CA    CN5  70  
CN5  H3D     H3D     H  0  1  N  N  N   9.979  -1.866  38.201  -19.625   1.329  -1.218  H3D     CN5  71  
CN5  H3DA    H3DA    H  0  0  N  N  N  11.383  -0.998  39.197  -19.742   0.767   0.467  H3DA    CN5  72  
CN5  H3E     H3E     H  0  1  N  N  N  12.856  -1.258  37.627  -20.611   2.987   1.148  H3E     CN5  73  
CN5  H3EA    H3EA    H  0  0  N  N  N  12.016  -2.719  36.909  -20.495   3.549  -0.537  H3EA    CN5  74  
CN5  H3F     H3F     H  0  1  N  N  N  11.128   0.204  36.587  -22.806   2.829   0.003  H3F     CN5  75  
CN5  H3FA    H3FA    H  0  0  N  N  N  11.952  -0.791  35.338  -22.083   1.778  -1.238  H3FA    CN5  76  
CN5  H3FB    H3FB    H  0  0  N  N  N  10.305  -1.237  35.900  -22.199   1.216   0.447  H3FB    CN5  77  
CN5  "HO4'"  "HO4'"  H  0  0  N  N  N  26.652   7.654  50.818   10.550  -1.520   1.840  "HO4'"  CN5  78  
CN5  "H1'"   "H1'"   H  0  1  N  N  N  24.808   6.718  48.415   12.725   0.314   0.447  "H1'"   CN5  79  
CN5  "H1'A"  "H1'A"  H  0  0  N  N  N  24.697   5.859  50.190   12.334   0.739  -1.237  "H1'A"  CN5  80  
CN5  "H2'"   "H2'"   H  0  1  N  N  N  22.807   4.692  48.950   11.848   3.068  -0.535  "H2'"   CN5  81  
CN5  "H2'A"  "H2'A"  H  0  0  N  N  N  23.782   4.922  47.583   12.239   2.642   1.148  "H2'A"  CN5  82  
CN5  "H3'"   "H3'"   H  0  1  N  N  N  25.828   4.457  48.971   14.541   2.030   0.459  "H3'"   CN5  83  
CN5  "H3'A"  "H3'A"  H  0  0  N  N  N  24.776   4.223  50.383   14.150   2.456  -1.225  "H3'A"  CN5  84  
CN5  H42     H42     H  0  1  N  N  N  25.862   0.637  46.669   16.985   6.004  -0.045  H42     CN5  85  
CN5  H42A    H42A    H  0  0  N  N  N  26.724   0.869  48.227   15.343   6.546  -0.468  H42A    CN5  86  
CN5  H42B    H42B    H  0  0  N  N  N  24.999   0.366  48.221   15.734   6.121   1.216  H42B    CN5  87  
CN5  HA      HA      H  0  1  N  N  N  24.234  10.006  48.112    7.577  -1.980  -1.111  HA      CN5  88  
CN5  HAA     HAA     H  0  1  N  N  N  25.974  10.074  47.529    7.813  -2.494   0.577  HAA     CN5  89  
CN5  HB      HB      H  0  1  N  N  N  24.511   7.558  46.986    5.879  -0.308  -0.313  HB      CN5  90  
CN5  HOA     HOA     H  0  1  N  N  N  25.608   8.338  44.756    6.244  -1.635   2.243  HOA     CN5  91  
CN5  HC      HC      H  0  1  N  N  N  23.814  10.204  45.488    5.312  -3.169   0.583  HC      CN5  92  
CN5  HCA     HCA     H  0  1  N  N  N  22.676   9.215  46.515    5.249  -2.608  -1.105  HCA     CN5  93  
#   #
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
CN5  O14    P       DOUB  N  N   1  
CN5  O12    P       SING  N  N   2  
CN5  P      O11     SING  N  N   3  
CN5  P      O13     SING  N  N   4  
CN5  O11    C1      SING  N  N   5  
CN5  O12    HO12    SING  N  N   6  
CN5  O13    CC      SING  N  N   7  
CN5  C2     C1      SING  N  N   8  
CN5  C1     H1      SING  N  N   9  
CN5  C1     H1A     SING  N  N  10  
CN5  C2     C3      SING  N  N  11  
CN5  C2     H2      SING  N  N  12  
CN5  C2     H2A     SING  N  N  13  
CN5  O31    C3      SING  N  N  14  
CN5  C3     H3      SING  N  N  15  
CN5  C3     H3A     SING  N  N  16  
CN5  O31    C31     SING  N  N  17  
CN5  C31    O32     DOUB  N  N  18  
CN5  C32    C31     SING  N  N  19  
CN5  C33    C32     SING  N  N  20  
CN5  C32    H32     SING  N  N  21  
CN5  C32    H32A    SING  N  N  22  
CN5  C33    C34     SING  N  N  23  
CN5  C33    H33     SING  N  N  24  
CN5  C33    H33A    SING  N  N  25  
CN5  C35    C34     SING  N  N  26  
CN5  C34    H34     SING  N  N  27  
CN5  C34    H34A    SING  N  N  28  
CN5  C35    C36     SING  N  N  29  
CN5  C35    H35     SING  N  N  30  
CN5  C35    H35A    SING  N  N  31  
CN5  C37    C36     SING  N  N  32  
CN5  C36    H36     SING  N  N  33  
CN5  C36    H36A    SING  N  N  34  
CN5  C37    C38     SING  N  N  35  
CN5  C37    H37     SING  N  N  36  
CN5  C37    H37A    SING  N  N  37  
CN5  C39    C38     SING  N  N  38  
CN5  C38    H38     SING  N  N  39  
CN5  C38    H38A    SING  N  N  40  
CN5  C39    C3A     SING  N  N  41  
CN5  C39    H39     SING  N  N  42  
CN5  C39    H39A    SING  N  N  43  
CN5  C3B    C3A     SING  N  N  44  
CN5  C3A    H3AA    SING  N  N  45  
CN5  C3A    H3AB    SING  N  N  46  
CN5  C3C    C3B     SING  N  N  47  
CN5  C3B    H3B     SING  N  N  48  
CN5  C3B    H3BA    SING  N  N  49  
CN5  C3D    C3C     SING  N  N  50  
CN5  C3C    H3C     SING  N  N  51  
CN5  C3C    H3CA    SING  N  N  52  
CN5  C3E    C3D     SING  N  N  53  
CN5  C3D    H3D     SING  N  N  54  
CN5  C3D    H3DA    SING  N  N  55  
CN5  C3F    C3E     SING  N  N  56  
CN5  C3E    H3E     SING  N  N  57  
CN5  C3E    H3EA    SING  N  N  58  
CN5  C3F    H3F     SING  N  N  59  
CN5  C3F    H3FA    SING  N  N  60  
CN5  C3F    H3FB    SING  N  N  61  
CN5  "O3'"  "P'"    SING  N  N  62  
CN5  "O1'"  "P'"    SING  N  N  63  
CN5  "P'"   "O2'"   DOUB  N  N  64  
CN5  "P'"   "O4'"   SING  N  N  65  
CN5  "C1'"  "O1'"   SING  N  N  66  
CN5  CA     "O3'"   SING  N  N  67  
CN5  "O4'"  "HO4'"  SING  N  N  68  
CN5  "C2'"  "C1'"   SING  N  N  69  
CN5  "C1'"  "H1'"   SING  N  N  70  
CN5  "C1'"  "H1'A"  SING  N  N  71  
CN5  "C2'"  "C3'"   SING  N  N  72  
CN5  "C2'"  "H2'"   SING  N  N  73  
CN5  "C2'"  "H2'A"  SING  N  N  74  
CN5  O41    "C3'"   SING  N  N  75  
CN5  "C3'"  "H3'"   SING  N  N  76  
CN5  "C3'"  "H3'A"  SING  N  N  77  
CN5  C41    O41     SING  N  N  78  
CN5  O42    C41     DOUB  N  N  79  
CN5  C42    C41     SING  N  N  80  
CN5  C42    H42     SING  N  N  81  
CN5  C42    H42A    SING  N  N  82  
CN5  C42    H42B    SING  N  N  83  
CN5  CB     CA      SING  N  N  84  
CN5  CA     HA      SING  N  N  85  
CN5  CA     HAA     SING  N  N  86  
CN5  OA     CB      SING  N  N  87  
CN5  CC     CB      SING  N  N  88  
CN5  CB     HB      SING  N  N  89  
CN5  OA     HOA     SING  N  N  90  
CN5  CC     HC      SING  N  N  91  
CN5  CC     HCA     SING  N  N  92  
#   #
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
CN5  SMILES            ACDLabs               10.04  "O=C(OCCCOP(=O)(OCC(O)COP(=O)(O)OCCCOC(=O)C)O)CCCCCCCCCCCCCC"  
CN5  SMILES_CANONICAL  CACTVS                3.341  "CCCCCCCCCCCCCCC(=O)OCCCO[P@@](O)(=O)OC[C@@H](O)CO[P@@](O)(=O)OCCCOC(C)=O"  
CN5  SMILES            CACTVS                3.341  "CCCCCCCCCCCCCCC(=O)OCCCO[P](O)(=O)OC[CH](O)CO[P](O)(=O)OCCCOC(C)=O"  
CN5  SMILES_CANONICAL  "OpenEye OEToolkits"  1.5.0  "CCCCCCCCCCCCCCC(=O)OCCCO[P@](=O)(O)OC[C@H](CO[P@](=O)(O)OCCCOC(=O)C)O"  
CN5  SMILES            "OpenEye OEToolkits"  1.5.0  "CCCCCCCCCCCCCCC(=O)OCCCOP(=O)(O)OCC(COP(=O)(O)OCCCOC(=O)C)O"  
CN5  InChI             InChI                 1.03   "InChI=1S/C26H52O13P2/c1-3-4-5-6-7-8-9-10-11-12-13-14-17-26(29)35-19-16-21-37-41(32,33)39-23-25(28)22-38-40(30,31)36-20-15-18-34-24(2)27/h25,28H,3-23H2,1-2H3,(H,30,31)(H,32,33)/t25-/m0/s1"  
CN5  InChIKey          InChI                 1.03   UKWPDXFRXMWSMQ-VWLOTQADSA-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
CN5  "SYSTEMATIC NAME"  ACDLabs               10.04  "(5S,11R)-5,8,11-trihydroxy-5,11-dioxido-17-oxo-4,6,10,12,16-pentaoxa-5,11-diphosphaoctadec-1-yl pentadecanoate"  
CN5  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.5.0  "3-[[(2S)-3-(3-acetyloxypropoxy-hydroxy-phosphoryl)oxy-2-hydroxy-propoxy]-hydroxy-phosphoryl]oxypropyl pentadecanoate"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
CN5  "Create component"   2008-04-28  RCSB  
CN5  "Modify descriptor"  2011-06-04  RCSB  
CN5  "Modify synonyms"    2021-03-01  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     CN5
_pdbx_chem_comp_synonyms.name        CARDIOLIPIN
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
