data_3EV
#

_chem_comp.id                                   3EV
_chem_comp.name                                 "(1S,3S,5Z,7E,14beta,17alpha)-9,10-secocholesta-5,7,10-triene-1,3,25-triol"
_chem_comp.type                                 NON-POLYMER
_chem_comp.pdbx_type                            HETAIN
_chem_comp.formula                              "C27 H44 O3"
_chem_comp.mon_nstd_parent_comp_id              ?
_chem_comp.pdbx_synonyms                        "1alpha,25-dihydroxy-3-epi-vitamin D3"
_chem_comp.pdbx_formal_charge                   0
_chem_comp.pdbx_initial_date                    2009-09-30
_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                       416.636
_chem_comp.one_letter_code                      ?
_chem_comp.three_letter_code                    3EV
_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       3A78
_chem_comp.pdbx_subcomponent_list               ?
_chem_comp.pdbx_processing_site                 PDBJ
#   #
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
3EV  C1    C1    C  0  1  N  N  S  13.971  17.194  35.700   5.575  -2.091   0.689  C1    3EV   1  
3EV  O1    O1    O  0  1  N  N  N  12.869  16.641  36.414   5.307  -3.481   0.881  O1    3EV   2  
3EV  C2    C2    C  0  1  N  N  N  14.671  16.093  34.901   6.785  -1.921  -0.235  C2    3EV   3  
3EV  O2    O2    O  0  1  N  N  N  16.566  15.604  33.462   8.247  -0.279  -1.234  O2    3EV   4  
3EV  C3    C3    C  0  1  N  N  S  15.844  16.674  34.101   7.034  -0.435  -0.495  C3    3EV   5  
3EV  O3    O3    O  0  1  N  N  N   4.525  26.072  34.730  -7.940  -0.568  -1.368  O3    3EV   6  
3EV  C4    C4    C  0  1  N  N  N  15.339  17.701  33.071   5.870   0.154  -1.297  C4    3EV   7  
3EV  C5    C5    C  0  1  N  N  N  14.515  18.755  33.780   4.590  -0.073  -0.517  C5    3EV   8  
3EV  C6    C6    C  0  1  N  N  N  14.718  20.058  33.488   3.687   0.913  -0.338  C6    3EV   9  
3EV  C7    C7    C  0  1  N  N  N  14.007  21.176  34.124   2.461   0.655   0.422  C7    3EV  10  
3EV  C8    C8    C  0  1  N  N  N  13.784  22.384  33.565   1.569   1.629   0.599  C8    3EV  11  
3EV  C9    C9    C  0  1  N  N  N  14.191  22.733  32.146   1.768   3.029   0.036  C9    3EV  12  
3EV  C10   C10   C  0  1  N  N  N  13.521  18.266  34.746   4.379  -1.426   0.037  C10   3EV  13  
3EV  C11   C11   C  0  1  N  N  N  12.956  23.283  31.404   0.528   3.485  -0.730  C11   3EV  14  
3EV  C12   C12   C  0  1  N  N  N  12.166  24.344  32.198  -0.760   3.251   0.077  C12   3EV  15  
3EV  C13   C13   C  0  1  N  N  R  11.755  23.839  33.588  -0.849   1.773   0.376  C13   3EV  16  
3EV  C14   C14   C  0  1  N  N  S  13.061  23.489  34.297   0.294   1.422   1.362  C14   3EV  17  
3EV  C15   C15   C  0  1  N  N  N  12.704  23.335  35.781  -0.062  -0.021   1.726  C15   3EV  18  
3EV  C16   C16   C  0  1  N  N  N  11.542  24.325  35.961  -1.605   0.042   1.905  C16   3EV  19  
3EV  C17   C17   C  0  1  N  N  R  11.273  24.918  34.562  -2.091   1.253   1.083  C17   3EV  20  
3EV  C18   C18   C  0  1  N  N  N  10.824  22.620  33.476  -0.652   0.983  -0.919  C18   3EV  21  
3EV  C19   C19   C  0  1  N  N  N  12.269  18.712  34.762   3.194  -2.034  -0.034  C19   3EV  22  
3EV  C20   C20   C  0  1  N  N  R   9.911  25.632  34.319  -3.135   0.801   0.060  C20   3EV  23  
3EV  C21   C21   C  0  1  N  N  N   9.912  27.042  34.914  -3.631   2.013  -0.731  C21   3EV  24  
3EV  C22   C22   C  0  1  N  N  N   8.670  24.878  34.807  -4.312   0.150   0.788  C22   3EV  25  
3EV  C23   C23   C  0  1  N  N  N   7.404  25.283  34.041  -5.298  -0.413  -0.239  C23   3EV  26  
3EV  C24   C24   C  0  1  N  N  N   6.240  24.369  34.410  -6.476  -1.065   0.488  C24   3EV  27  
3EV  C25   C25   C  0  1  N  N  N   4.856  24.881  34.007  -7.460  -1.628  -0.538  C25   3EV  28  
3EV  C26   C26   C  0  1  N  N  N   4.803  25.212  32.523  -8.638  -2.279   0.189  C26   3EV  29  
3EV  C27   C27   C  0  1  N  N  N   3.818  23.816  34.344  -6.754  -2.673  -1.403  C27   3EV  30  
3EV  H1    H1    H  0  1  N  N  N  14.660  17.637  36.434   5.778  -1.620   1.651  H1    3EV  31  
3EV  HO1   HO1   H  0  1  N  N  N  12.436  17.326  36.909   4.552  -3.661   1.458  HO1   3EV  32  
3EV  H2    H2    H  0  1  N  N  N  15.051  15.329  35.596   7.665  -2.360   0.236  H2    3EV  33  
3EV  H2A   H2A   H  0  1  N  N  N  13.950  15.638  34.206   6.592  -2.427  -1.181  H2A   3EV  34  
3EV  HO2   HO2   H  0  1  N  N  N  17.293  15.963  32.966   8.469   0.640  -1.436  HO2   3EV  35  
3EV  H3    H3    H  0  1  N  N  N  16.527  17.199  34.784   7.120   0.089   0.456  H3    3EV  36  
3EV  HO3   HO3   H  0  1  N  N  N   3.664  26.374  34.466  -8.400   0.132  -0.886  HO3   3EV  37  
3EV  H4    H4    H  0  1  N  N  N  16.197  18.177  32.575   6.027   1.223  -1.441  H4    3EV  38  
3EV  H4A   H4A   H  0  1  N  N  N  14.718  17.193  32.319   5.802  -0.342  -2.265  H4A   3EV  39  
3EV  H6    H6    H  0  1  N  N  N  15.454  20.295  32.734   3.867   1.893  -0.755  H6    3EV  40  
3EV  H7    H7    H  0  1  N  N  N  13.631  21.017  35.124   2.281  -0.325   0.838  H7    3EV  41  
3EV  H9    H9    H  0  1  N  N  N  14.985  23.494  32.163   1.958   3.722   0.856  H9    3EV  42  
3EV  H9A   H9A   H  0  1  N  N  N  14.564  21.834  31.634   2.626   3.027  -0.637  H9A   3EV  43  
3EV  H11   H11   H  0  1  N  N  N  13.301  23.747  30.468   0.619   4.548  -0.954  H11   3EV  44  
3EV  H11A  H11A  H  0  0  N  N  N  12.280  22.440  31.199   0.466   2.930  -1.667  H11A  3EV  45  
3EV  H12   H12   H  0  1  N  N  N  12.801  25.234  32.322  -0.719   3.816   1.009  H12   3EV  46  
3EV  H12A  H12A  H  0  0  N  N  N  11.256  24.599  31.634  -1.625   3.563  -0.508  H12A  3EV  47  
3EV  H14   H14   H  0  1  N  N  N  13.843  24.263  34.274   0.261   2.069   2.239  H14   3EV  48  
3EV  H15   H15   H  0  1  N  N  N  12.402  22.305  36.022   0.206  -0.701   0.917  H15   3EV  49  
3EV  H15A  H15A  H  0  0  N  N  N  13.555  23.584  36.432   0.423  -0.315   2.656  H15A  3EV  50  
3EV  H16   H16   H  0  1  N  N  N  10.648  23.810  36.343  -2.063  -0.876   1.535  H16   3EV  51  
3EV  H16A  H16A  H  0  0  N  N  N  11.814  25.118  36.674  -1.855   0.188   2.956  H16A  3EV  52  
3EV  H17   H17   H  0  1  N  N  N  11.840  25.845  34.394  -2.505   2.022   1.735  H17   3EV  53  
3EV  H18   H18   H  0  1  N  N  N  10.544  22.278  34.483   0.366   1.127  -1.281  H18   3EV  54  
3EV  H18A  H18A  H  0  0  N  N  N   9.918  22.901  32.920  -0.823  -0.076  -0.728  H18A  3EV  55  
3EV  H18B  H18B  H  0  0  N  N  N  11.344  21.809  32.945  -1.358   1.336  -1.671  H18B  3EV  56  
3EV  H19   H19   H  0  1  N  N  N  11.953  19.459  34.049   3.070  -3.024   0.380  H19   3EV  57  
3EV  H19A  H19A  H  0  0  N  N  N  11.568  18.327  35.488   2.360  -1.536  -0.504  H19A  3EV  58  
3EV  H20   H20   H  0  1  N  N  N   9.828  25.669  33.223  -2.686   0.080  -0.623  H20   3EV  59  
3EV  H21   H21   H  0  1  N  N  N   8.939  27.520  34.727  -4.019   2.763  -0.042  H21   3EV  60  
3EV  H21A  H21A  H  0  0  N  N  N  10.089  26.982  35.998  -2.805   2.437  -1.302  H21A  3EV  61  
3EV  H21B  H21B  H  0  0  N  N  N  10.709  27.637  34.445  -4.423   1.702  -1.413  H21B  3EV  62  
3EV  H22   H22   H  0  1  N  N  N   8.836  23.800  34.663  -3.947  -0.659   1.421  H22   3EV  63  
3EV  H22A  H22A  H  0  0  N  N  N   8.521  25.103  35.873  -4.816   0.895   1.404  H22A  3EV  64  
3EV  H23   H23   H  0  1  N  N  N   7.143  26.320  34.299  -5.664   0.395  -0.872  H23   3EV  65  
3EV  H23A  H23A  H  0  0  N  N  N   7.596  25.204  32.961  -4.794  -1.158  -0.855  H23A  3EV  66  
3EV  H24   H24   H  0  1  N  N  N   6.399  23.406  33.902  -6.109  -1.873   1.122  H24   3EV  67  
3EV  H24A  H24A  H  0  0  N  N  N   6.245  24.249  35.503  -6.979  -0.320   1.105  H24A  3EV  68  
3EV  H26   H26   H  0  1  N  N  N   5.053  24.315  31.938  -9.340  -2.680  -0.542  H26   3EV  69  
3EV  H26A  H26A  H  0  0  N  N  N   3.790  25.551  32.259  -8.272  -3.087   0.823  H26A  3EV  70  
3EV  H26B  H26B  H  0  0  N  N  N   5.527  26.009  32.299  -9.142  -1.534   0.805  H26B  3EV  71  
3EV  H27   H27   H  0  1  N  N  N   4.052  22.890  33.799  -5.915  -2.209  -1.921  H27   3EV  72  
3EV  H27A  H27A  H  0  0  N  N  N   3.834  23.618  35.426  -6.388  -3.481  -0.770  H27A  3EV  73  
3EV  H27B  H27B  H  0  0  N  N  N   2.819  24.172  34.050  -7.456  -3.074  -2.134  H27B  3EV  74  
#   #
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
3EV  C1   O1    SING  N  N   1  
3EV  C1   C2    SING  N  N   2  
3EV  C1   C10   SING  N  N   3  
3EV  C2   C3    SING  N  N   4  
3EV  O2   C3    SING  N  N   5  
3EV  C3   C4    SING  N  N   6  
3EV  O3   C25   SING  N  N   7  
3EV  C4   C5    SING  N  N   8  
3EV  C5   C6    DOUB  N  N   9  
3EV  C5   C10   SING  N  N  10  
3EV  C6   C7    SING  N  N  11  
3EV  C7   C8    DOUB  N  N  12  
3EV  C8   C9    SING  N  N  13  
3EV  C8   C14   SING  N  N  14  
3EV  C9   C11   SING  N  N  15  
3EV  C10  C19   DOUB  N  N  16  
3EV  C11  C12   SING  N  N  17  
3EV  C12  C13   SING  N  Z  18  
3EV  C13  C14   SING  N  N  19  
3EV  C13  C17   SING  N  N  20  
3EV  C13  C18   SING  N  N  21  
3EV  C14  C15   SING  N  E  22  
3EV  C15  C16   SING  N  N  23  
3EV  C16  C17   SING  N  N  24  
3EV  C17  C20   SING  N  N  25  
3EV  C20  C21   SING  N  N  26  
3EV  C20  C22   SING  N  N  27  
3EV  C22  C23   SING  N  N  28  
3EV  C23  C24   SING  N  N  29  
3EV  C24  C25   SING  N  N  30  
3EV  C25  C26   SING  N  N  31  
3EV  C25  C27   SING  N  N  32  
3EV  C1   H1    SING  N  N  33  
3EV  O1   HO1   SING  N  N  34  
3EV  C2   H2    SING  N  N  35  
3EV  C2   H2A   SING  N  N  36  
3EV  O2   HO2   SING  N  N  37  
3EV  C3   H3    SING  N  N  38  
3EV  O3   HO3   SING  N  N  39  
3EV  C4   H4    SING  N  N  40  
3EV  C4   H4A   SING  N  N  41  
3EV  C6   H6    SING  N  N  42  
3EV  C7   H7    SING  N  N  43  
3EV  C9   H9    SING  N  N  44  
3EV  C9   H9A   SING  N  N  45  
3EV  C11  H11   SING  N  N  46  
3EV  C11  H11A  SING  N  N  47  
3EV  C12  H12   SING  N  N  48  
3EV  C12  H12A  SING  N  N  49  
3EV  C14  H14   SING  N  N  50  
3EV  C15  H15   SING  N  N  51  
3EV  C15  H15A  SING  N  N  52  
3EV  C16  H16   SING  N  N  53  
3EV  C16  H16A  SING  N  N  54  
3EV  C17  H17   SING  N  N  55  
3EV  C18  H18   SING  N  N  56  
3EV  C18  H18A  SING  N  N  57  
3EV  C18  H18B  SING  N  N  58  
3EV  C19  H19   SING  N  N  59  
3EV  C19  H19A  SING  N  N  60  
3EV  C20  H20   SING  N  N  61  
3EV  C21  H21   SING  N  N  62  
3EV  C21  H21A  SING  N  N  63  
3EV  C21  H21B  SING  N  N  64  
3EV  C22  H22   SING  N  N  65  
3EV  C22  H22A  SING  N  N  66  
3EV  C23  H23   SING  N  N  67  
3EV  C23  H23A  SING  N  N  68  
3EV  C24  H24   SING  N  N  69  
3EV  C24  H24A  SING  N  N  70  
3EV  C26  H26   SING  N  N  71  
3EV  C26  H26A  SING  N  N  72  
3EV  C26  H26B  SING  N  N  73  
3EV  C27  H27   SING  N  N  74  
3EV  C27  H27A  SING  N  N  75  
3EV  C27  H27B  SING  N  N  76  
#   #
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
3EV  SMILES            ACDLabs               11.02  "OC3C(=C)\C(=C/C=C1\CCCC2(C)C(C(C)CCCC(O)(C)C)CCC12)CC(O)C3"  
3EV  SMILES_CANONICAL  CACTVS                3.352  "C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C(/CCC[C@]12C)=C/C=C3/C[C@H](O)C[C@H](O)C3=C"  
3EV  SMILES            CACTVS                3.352  "C[CH](CCCC(C)(C)O)[CH]1CC[CH]2C(CCC[C]12C)=CC=C3C[CH](O)C[CH](O)C3=C"  
3EV  SMILES_CANONICAL  "OpenEye OEToolkits"  1.7.0  "C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@@H](C[C@@H](C3=C)O)O)C"  
3EV  SMILES            "OpenEye OEToolkits"  1.7.0  "CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C"  
3EV  InChI             InChI                 1.03   "InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22+,23-,24+,25+,27-/m1/s1"  
3EV  InChIKey          InChI                 1.03   GMRQFYUYWCNGIN-GNVXBELXSA-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
3EV  "SYSTEMATIC NAME"  ACDLabs               11.02  "(1S,3S,5Z,7E,14beta,17alpha)-9,10-secocholesta-5,7,10-triene-1,3,25-triol"  
3EV  "SYSTEMATIC NAME"  "OpenEye OEToolkits"  1.6.1  "(1S,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methyl-heptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol"  
#   #
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
3EV  "Create component"   2009-09-30  PDBJ  
3EV  "Modify descriptor"  2011-06-04  RCSB  
3EV  "Modify synonyms"    2020-06-05  PDBE  
#
_pdbx_chem_comp_synonyms.ordinal     1
_pdbx_chem_comp_synonyms.comp_id     3EV
_pdbx_chem_comp_synonyms.name        "1alpha,25-dihydroxy-3-epi-vitamin D3"
_pdbx_chem_comp_synonyms.provenance  ?
_pdbx_chem_comp_synonyms.type        ?
##
