data_PDN
# 
_chem_comp.id                                    PDN 
_chem_comp.name                                  17,21-DIHYDROXYPREGNA-1,4-DIENE-3,11,20-TRIONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C21 H26 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "PREDNISONE; 1,4 PREGNADIENE-17ALPHA,21-DIOL-3,11,20-TRIONE; 1-CORTISONE; DEHYDROCORTISONE" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-06-04 
_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                        358.428 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     PDN 
_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        1H61 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  EBI 
# 
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 
PDN C1   C1   C 0 1 N N N 20.636 11.858 21.148 1.603  -0.072 -3.214 C1   PDN 1  
PDN C2   C2   C 0 1 N N N 19.883 10.851 21.762 1.622  -0.403 -4.495 C2   PDN 2  
PDN C3   C3   C 0 1 N N N 19.956 9.433  21.345 0.385  -0.324 -5.290 C3   PDN 3  
PDN C4   C4   C 0 1 N N N 20.859 9.125  20.232 -0.860 0.068  -4.613 C4   PDN 4  
PDN C5   C5   C 0 1 N N N 21.637 10.039 19.570 -0.858 0.388  -3.327 C5   PDN 5  
PDN C6   C6   C 0 1 N N N 22.618 9.609  18.360 -2.169 0.765  -2.663 C6   PDN 6  
PDN C7   C7   C 0 1 N N N 22.385 10.589 17.290 -2.323 -0.063 -1.382 C7   PDN 7  
PDN C8   C8   C 0 1 N N S 22.390 11.970 17.560 -1.088 0.131  -0.505 C8   PDN 8  
PDN C9   C9   C 0 1 N N S 21.341 12.358 18.721 0.143  -0.436 -1.233 C9   PDN 9  
PDN C10  C10  C 0 1 N N R 21.612 11.562 19.981 0.382  0.405  -2.487 C10  PDN 10 
PDN C11  C11  C 0 1 N N N 21.330 13.943 18.938 1.348  -0.394 -0.330 C11  PDN 11 
PDN C12  C12  C 0 1 N N N 21.101 14.666 17.593 1.225  -0.891 1.102  C12  PDN 12 
PDN C13  C13  C 0 1 N N S 22.101 14.363 16.544 -0.000 -0.212 1.690  C13  PDN 13 
PDN C14  C14  C 0 1 N N S 22.080 12.841 16.314 -1.219 -0.605 0.811  C14  PDN 14 
PDN C15  C15  C 0 1 N N N 22.957 12.710 15.016 -2.408 -0.181 1.684  C15  PDN 15 
PDN C16  C16  C 0 1 N N N 22.777 13.884 14.262 -1.969 -0.609 3.109  C16  PDN 16 
PDN C17  C17  C 0 1 N N R 21.792 14.776 15.064 -0.398 -0.669 3.091  C17  PDN 17 
PDN C18  C18  C 0 1 N N N 23.498 14.949 17.028 0.186  1.306  1.671  C18  PDN 18 
PDN C19  C19  C 0 1 N N N 22.949 11.949 20.581 0.629  1.851  -2.049 C19  PDN 19 
PDN C20  C20  C 0 1 N N N 21.841 16.327 14.937 0.170  0.253  4.138  C20  PDN 20 
PDN C21  C21  C 0 1 N N N 20.827 16.768 14.703 0.951  -0.228 5.088  C21  PDN 21 
PDN O1   O1   O 0 1 N N N 19.314 8.600  21.893 0.392  -0.579 -6.480 O1   PDN 22 
PDN O2   O2   O 0 1 N N N 21.468 14.574 20.145 2.402  0.029  -0.740 O2   PDN 23 
PDN O3   O3   O 0 1 N N N 20.340 14.400 14.830 0.047  -2.008 3.315  O3   PDN 24 
PDN O4   O4   O 0 1 N N N 22.872 16.659 14.207 -0.121 1.581  4.106  O4   PDN 25 
PDN O5   O5   O 0 1 N N N 20.922 18.125 15.144 1.464  0.604  6.033  O5   PDN 26 
PDN HC1  1HC  H 0 1 N N N 20.532 12.896 21.506 2.526  -0.148 -2.658 HC1  PDN 27 
PDN HC2  2HC  H 0 1 N N N 19.208 11.125 22.590 2.542  -0.730 -4.957 HC2  PDN 28 
PDN HC4  4HC  H 0 1 N N N 20.917 8.074  19.901 -1.785 0.096  -5.170 HC4  PDN 29 
PDN HC61 1HC6 H 0 0 N N N 22.486 8.551  18.033 -2.996 0.551  -3.339 HC61 PDN 30 
PDN HC62 2HC6 H 0 0 N N N 23.688 9.523  18.662 -2.161 1.826  -2.413 HC62 PDN 31 
PDN HC71 1HC7 H 0 0 N N N 21.419 10.337 16.793 -2.424 -1.117 -1.640 HC71 PDN 32 
PDN HC72 2HC7 H 0 0 N N N 23.119 10.393 16.474 -3.210 0.265  -0.840 HC72 PDN 33 
PDN HC8  8HC  H 0 1 N N N 23.410 12.242 17.919 -0.940 1.194  -0.315 HC8  PDN 34 
PDN HC9  9HC  H 0 1 N N N 20.327 12.068 18.360 -0.053 -1.468 -1.524 HC9  PDN 35 
PDN H121 1H12 H 0 0 N N N 21.033 15.767 17.754 2.113  -0.616 1.671  H121 PDN 36 
PDN H122 2H12 H 0 0 N N N 20.072 14.461 17.215 1.094  -1.973 1.112  H122 PDN 37 
PDN HC41 1HC4 H 0 0 N N N 21.037 12.588 16.010 -1.237 -1.682 0.643  HC41 PDN 38 
PDN H151 1H15 H 0 0 N N N 22.738 11.783 14.436 -2.556 0.897  1.634  H151 PDN 39 
PDN H152 2H15 H 0 0 N N N 24.029 12.495 15.236 -3.313 -0.709 1.385  H152 PDN 40 
PDN H161 1H16 H 0 0 N N N 23.734 14.398 14.011 -2.309 0.122  3.841  H161 PDN 41 
PDN H162 2H16 H 0 0 N N N 22.445 13.690 13.215 -2.375 -1.592 3.346  H162 PDN 42 
PDN H181 1H18 H 0 0 N N N 23.513 16.051 17.195 0.420  1.630  0.657  H181 PDN 43 
PDN H182 2H18 H 0 0 N N N 24.306 14.656 16.318 -0.731 1.789  2.005  H182 PDN 44 
PDN H183 3H18 H 0 0 N N N 23.843 14.416 17.945 1.004  1.579  2.338  H183 PDN 45 
PDN H191 1H19 H 0 0 N N N 23.651 11.736 19.741 0.811  2.470  -2.928 H191 PDN 46 
PDN H192 2H19 H 0 0 N N N 23.198 11.445 21.544 -0.245 2.224  -1.517 H192 PDN 47 
PDN H193 3H19 H 0 0 N N N 23.001 12.986 20.988 1.498  1.888  -1.392 H193 PDN 48 
PDN HC12 2HC1 H 0 0 N N N 19.972 16.204 15.142 1.183  -1.282 5.114  HC12 PDN 49 
PDN HO3  3HO  H 0 1 N N N 20.153 14.650 13.933 -0.270 -2.266 4.191  HO3  PDN 50 
PDN HO4  4HO  H 0 1 N N N 22.902 17.605 14.130 0.336  1.986  4.855  HO4  PDN 51 
PDN HO5  5HO  H 0 1 N N N 20.070 18.496 14.947 2.001  0.059  6.624  HO5  PDN 52 
# 
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 
PDN C1  C2   DOUB N N 1  
PDN C1  C10  SING N N 2  
PDN C1  HC1  SING N N 3  
PDN C2  C3   SING N N 4  
PDN C2  HC2  SING N N 5  
PDN C3  C4   SING N N 6  
PDN C3  O1   DOUB N N 7  
PDN C4  C5   DOUB N N 8  
PDN C4  HC4  SING N N 9  
PDN C5  C6   SING N N 10 
PDN C5  C10  SING N N 11 
PDN C6  C7   SING N N 12 
PDN C6  HC61 SING N N 13 
PDN C6  HC62 SING N N 14 
PDN C7  C8   SING N N 15 
PDN C7  HC71 SING N N 16 
PDN C7  HC72 SING N N 17 
PDN C8  C9   SING N N 18 
PDN C8  C14  SING N N 19 
PDN C8  HC8  SING N N 20 
PDN C9  C10  SING N N 21 
PDN C9  C11  SING N N 22 
PDN C9  HC9  SING N N 23 
PDN C10 C19  SING N N 24 
PDN C11 C12  SING N N 25 
PDN C11 O2   DOUB N N 26 
PDN C12 C13  SING N N 27 
PDN C12 H121 SING N N 28 
PDN C12 H122 SING N N 29 
PDN C13 C14  SING N N 30 
PDN C13 C17  SING N N 31 
PDN C13 C18  SING N N 32 
PDN C14 C15  SING N N 33 
PDN C14 HC41 SING N N 34 
PDN C15 C16  SING N N 35 
PDN C15 H151 SING N N 36 
PDN C15 H152 SING N N 37 
PDN C16 C17  SING N N 38 
PDN C16 H161 SING N N 39 
PDN C16 H162 SING N N 40 
PDN C17 C20  SING N N 41 
PDN C17 O3   SING N N 42 
PDN C18 H181 SING N N 43 
PDN C18 H182 SING N N 44 
PDN C18 H183 SING N N 45 
PDN C19 H191 SING N N 46 
PDN C19 H192 SING N N 47 
PDN C19 H193 SING N N 48 
PDN C20 C21  DOUB N Z 49 
PDN C20 O4   SING N N 50 
PDN C21 O5   SING N N 51 
PDN C21 HC12 SING N N 52 
PDN O3  HO3  SING N N 53 
PDN O4  HO4  SING N N 54 
PDN O5  HO5  SING N N 55 
# 
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 
PDN SMILES           ACDLabs              10.04 O=C2CC4(C(C3CCC1=CC(=O)C=CC1(C)C23)CCC4(O)C(\O)=C\O)C                                                                                                                                     
PDN InChI            InChI                1.02b InChI=1/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,11,14-15,18,22,25-26H,3-4,6,8,10H2,1-2H3/b17-11-/t14-,15-,18+,19-,20-,21-/m0/s1 
PDN InChIKey         InChI                1.02b WZTZVUUYKIOIRV-LMZHSBCYBG                                                                                                                                                                 
PDN SMILES_CANONICAL CACTVS               3.341 C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@]2(O)\C(O)=C\O                                                                                                                
PDN SMILES           CACTVS               3.341 C[C]12CC(=O)[CH]3[CH](CCC4=CC(=O)C=C[C]34C)[CH]1CC[C]2(O)C(O)=CO                                                                                                                          
PDN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@]12CC(=O)[C@H]3[C@H]([C@@H]1CC[C@@]2(C(=CO)O)O)CCC4=CC(=O)C=C[C@]34C                                                                                                                  
PDN SMILES           "OpenEye OEToolkits" 1.5.0 CC12CC(=O)C3C(C1CCC2(C(=CO)O)O)CCC4=CC(=O)C=CC34C                                                                                                                                         
# 
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 
PDN "SYSTEMATIC NAME" ACDLabs              10.04 (8alpha,14beta,17alpha,20Z)-17,20,21-trihydroxypregna-1,4,20-triene-3,11-dione                                                                
PDN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (8S,9S,10R,13S,14S,17R)-17-(1,2-dihydroxyethenyl)-17-hydroxy-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione 
# 
