data_SIH
# 
_chem_comp.id                                    SIH 
_chem_comp.name                                  PROGESTERONE-11-ALPHA-OL-HEMISUCCINATE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H34 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        430.534 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     SIH 
_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        1DBM 
_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 
SIH C1   C1   C 0 1 N N N -19.826 43.050 -15.239 -1.948 -0.291 1.623  C1   SIH 1  
SIH C2   C2   C 0 1 N N N -18.511 42.503 -15.702 -2.903 0.773  2.161  C2   SIH 2  
SIH C3   C3   C 0 1 N N N -17.517 43.501 -15.199 -4.312 0.361  1.778  C3   SIH 3  
SIH O3   O3   O 0 1 N N N -16.845 44.211 -15.947 -5.203 0.281  2.597  O3   SIH 4  
SIH C4   C4   C 0 1 N N N -17.399 43.629 -13.851 -4.533 0.065  0.356  C4   SIH 5  
SIH C5   C5   C 0 1 N N N -18.558 43.488 -13.104 -3.503 -0.325 -0.389 C5   SIH 6  
SIH C6   C6   C 0 1 N N N -18.581 43.566 -11.689 -3.725 -0.589 -1.868 C6   SIH 7  
SIH C7   C7   C 0 1 N N N -19.423 44.726 -11.313 -2.700 0.243  -2.647 C7   SIH 8  
SIH C8   C8   C 0 1 N N S -20.823 44.379 -11.698 -1.287 -0.079 -2.163 C8   SIH 9  
SIH C9   C9   C 0 1 N N S -20.942 44.245 -13.246 -1.126 0.301  -0.681 C9   SIH 10 
SIH C10  C10  C 0 1 N N R -19.945 43.154 -13.722 -2.117 -0.520 0.142  C10  SIH 11 
SIH C11  C11  C 0 1 N N R -22.457 43.813 -13.628 0.292  0.035  -0.188 C11  SIH 12 
SIH O11  O11  O 0 1 N N N -22.682 43.934 -15.035 0.420  0.523  1.172  O11  SIH 13 
SIH C12  C12  C 0 1 N N N -23.431 44.739 -12.878 1.339  0.734  -1.071 C12  SIH 14 
SIH C13  C13  C 0 1 N N S -23.130 45.043 -11.402 1.146  0.282  -2.491 C13  SIH 15 
SIH C14  C14  C 0 1 N N S -21.733 45.465 -11.224 -0.270 0.725  -2.951 C14  SIH 16 
SIH C15  C15  C 0 1 N N N -21.730 46.058 -9.821  -0.213 0.437  -4.456 C15  SIH 17 
SIH C16  C16  C 0 1 N N N -23.199 46.456 -9.554  1.206  0.927  -4.850 C16  SIH 18 
SIH C17  C17  C 0 1 N N S -24.004 46.101 -10.791 2.060  0.874  -3.558 C17  SIH 19 
SIH C18  C18  C 0 1 N N N -23.294 43.720 -10.640 1.192  -1.244 -2.560 C18  SIH 20 
SIH C19  C19  C 0 1 N N N -20.390 41.756 -13.260 -1.749 -1.981 -0.121 C19  SIH 21 
SIH C20  C20  C 0 1 N N N -25.465 45.790 -10.599 3.263  -0.009 -3.764 C20  SIH 22 
SIH O20  O20  O 0 1 N N N -25.859 44.988 -9.762  3.227  -0.899 -4.580 O20  SIH 23 
SIH C21  C21  C 0 1 N N N -26.493 46.464 -11.468 4.512  0.216  -2.951 C21  SIH 24 
SIH CH1  CH1  C 0 1 N N N -23.214 43.003 -15.724 1.272  -0.072 2.021  CH1  SIH 25 
SIH OH1  OH1  O 0 1 N N N -23.294 42.971 -16.978 1.932  -1.014 1.653  OH1  SIH 26 
SIH CH2  CH2  C 0 1 N N N -23.919 41.814 -15.157 1.405  0.434  3.435  CH2  SIH 27 
SIH CH3  CH3  C 0 1 N N N -25.431 42.026 -15.391 2.433  -0.413 4.186  CH3  SIH 28 
SIH CH4  CH4  C 0 1 N N N -25.950 40.992 -16.390 2.566  0.092  5.599  CH4  SIH 29 
SIH OH4  OH4  O 0 1 N N N -25.673 41.213 -17.594 1.906  1.035  5.967  OH4  SIH 30 
SIH OH5  OH5  O 0 1 N N N -26.518 39.937 -15.954 3.418  -0.502 6.448  OH5  SIH 31 
SIH H11A 1H1  H 0 0 N N N -20.033 44.034 -15.718 -0.923 0.023  1.817  H11A SIH 32 
SIH H12  2H1  H 0 1 N N N -20.670 42.455 -15.660 -2.133 -1.228 2.148  H12  SIH 33 
SIH H21  1H2  H 0 1 N N N -18.311 41.453 -15.384 -2.666 1.740  1.717  H21  SIH 34 
SIH H22  2H2  H 0 1 N N N -18.453 42.307 -16.798 -2.817 0.832  3.246  H22  SIH 35 
SIH H41  1H4  H 0 1 N N N -16.418 43.835 -13.389 -5.517 0.164  -0.078 H41  SIH 36 
SIH H61  1H6  H 0 1 N N N -18.913 42.616 -11.208 -4.735 -0.290 -2.150 H61  SIH 37 
SIH H62  2H6  H 0 1 N N N -17.560 43.608 -11.241 -3.579 -1.648 -2.081 H62  SIH 38 
SIH H71  1H7  H 0 1 N N N -19.319 45.016 -10.241 -2.902 1.303  -2.492 H71  SIH 39 
SIH H72  2H7  H 0 1 N N N -19.070 45.687 -11.753 -2.780 0.013  -3.710 H72  SIH 40 
SIH H8   H8   H 0 1 N N N -21.104 43.405 -11.232 -1.090 -1.144 -2.291 H8   SIH 41 
SIH H9   H9   H 0 1 N N N -20.704 45.215 -13.741 -1.354 1.361  -0.566 H9   SIH 42 
SIH H11  H11  H 0 1 N N N -22.618 42.748 -13.336 0.477  -1.038 -0.200 H11  SIH 43 
SIH H121 1H12 H 0 0 N N N -23.532 45.697 -13.438 1.194  1.814  -1.034 H121 SIH 44 
SIH H122 2H12 H 0 0 N N N -24.466 44.334 -12.966 2.342  0.482  -0.727 H122 SIH 45 
SIH H14  H14  H 0 1 N N N -21.292 46.275 -11.850 -0.411 1.791  -2.774 H14  SIH 46 
SIH H151 1H15 H 0 0 N N N -21.296 45.383 -9.046  -0.978 1.005  -4.986 H151 SIH 47 
SIH H152 2H15 H 0 0 N N N -21.003 46.892 -9.684  -0.321 -0.629 -4.649 H152 SIH 48 
SIH H161 1H16 H 0 0 N N N -23.609 45.999 -8.623  1.159  1.949  -5.226 H161 SIH 49 
SIH H162 2H16 H 0 0 N N N -23.311 47.524 -9.255  1.632  0.268  -5.607 H162 SIH 50 
SIH H17  H17  H 0 1 N N N -24.185 46.963 -11.473 2.375  1.878  -3.272 H17  SIH 51 
SIH H181 1H18 H 0 0 N N N -23.075 43.940 -9.569  0.466  -1.662 -1.862 H181 SIH 52 
SIH H182 2H18 H 0 0 N N N -24.288 43.240 -10.797 0.952  -1.570 -3.572 H182 SIH 53 
SIH H183 3H18 H 0 0 N N N -22.673 42.892 -11.055 2.191  -1.590 -2.295 H183 SIH 54 
SIH H191 1H19 H 0 0 N N N -20.477 41.832 -12.151 -2.412 -2.631 0.449  H191 SIH 55 
SIH H192 2H19 H 0 0 N N N -21.315 41.388 -13.761 -1.856 -2.197 -1.184 H192 SIH 56 
SIH H193 3H19 H 0 0 N N N -19.721 40.932 -13.605 -0.717 -2.157 0.183  H193 SIH 57 
SIH H211 1H21 H 0 0 N N N -27.574 46.233 -11.325 5.269  -0.514 -3.236 H211 SIH 58 
SIH H212 2H21 H 0 0 N N N -26.352 47.567 -11.391 4.890  1.221  -3.136 H212 SIH 59 
SIH H213 3H21 H 0 0 N N N -26.229 46.280 -12.535 4.281  0.104  -1.891 H213 SIH 60 
SIH HH21 1HH2 H 0 0 N N N -23.544 40.847 -15.567 1.732  1.473  3.419  HH21 SIH 61 
SIH HH22 2HH2 H 0 0 N N N -23.664 41.623 -14.088 0.440  0.365  3.937  HH22 SIH 62 
SIH HH31 1HH3 H 0 0 N N N -26.008 42.014 -14.437 2.106  -1.453 4.201  HH31 SIH 63 
SIH HH32 2HH3 H 0 0 N N N -25.664 43.069 -15.708 3.398  -0.344 3.683  HH32 SIH 64 
SIH HOH5 5HOH H 0 0 N N N -26.840 39.294 -16.574 3.503  -0.178 7.355  HOH5 SIH 65 
# 
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 
SIH C1  C2   SING N N 1  
SIH C1  C10  SING N N 2  
SIH C1  H11A SING N N 3  
SIH C1  H12  SING N N 4  
SIH C2  C3   SING N N 5  
SIH C2  H21  SING N N 6  
SIH C2  H22  SING N N 7  
SIH C3  O3   DOUB N N 8  
SIH C3  C4   SING N N 9  
SIH C4  C5   DOUB N N 10 
SIH C4  H41  SING N N 11 
SIH C5  C6   SING N N 12 
SIH C5  C10  SING N N 13 
SIH C6  C7   SING N N 14 
SIH C6  H61  SING N N 15 
SIH C6  H62  SING N N 16 
SIH C7  C8   SING N N 17 
SIH C7  H71  SING N N 18 
SIH C7  H72  SING N N 19 
SIH C8  C9   SING N N 20 
SIH C8  C14  SING N N 21 
SIH C8  H8   SING N N 22 
SIH C9  C10  SING N N 23 
SIH C9  C11  SING N N 24 
SIH C9  H9   SING N N 25 
SIH C10 C19  SING N N 26 
SIH C11 O11  SING N N 27 
SIH C11 C12  SING N N 28 
SIH C11 H11  SING N N 29 
SIH O11 CH1  SING N N 30 
SIH C12 C13  SING N N 31 
SIH C12 H121 SING N N 32 
SIH C12 H122 SING N N 33 
SIH C13 C14  SING N N 34 
SIH C13 C17  SING N N 35 
SIH C13 C18  SING N N 36 
SIH C14 C15  SING N N 37 
SIH C14 H14  SING N N 38 
SIH C15 C16  SING N N 39 
SIH C15 H151 SING N N 40 
SIH C15 H152 SING N N 41 
SIH C16 C17  SING N N 42 
SIH C16 H161 SING N N 43 
SIH C16 H162 SING N N 44 
SIH C17 C20  SING N N 45 
SIH C17 H17  SING N N 46 
SIH C18 H181 SING N N 47 
SIH C18 H182 SING N N 48 
SIH C18 H183 SING N N 49 
SIH C19 H191 SING N N 50 
SIH C19 H192 SING N N 51 
SIH C19 H193 SING N N 52 
SIH C20 O20  DOUB N N 53 
SIH C20 C21  SING N N 54 
SIH C21 H211 SING N N 55 
SIH C21 H212 SING N N 56 
SIH C21 H213 SING N N 57 
SIH CH1 OH1  DOUB N N 58 
SIH CH1 CH2  SING N N 59 
SIH CH2 CH3  SING N N 60 
SIH CH2 HH21 SING N N 61 
SIH CH2 HH22 SING N N 62 
SIH CH3 CH4  SING N N 63 
SIH CH3 HH31 SING N N 64 
SIH CH3 HH32 SING N N 65 
SIH CH4 OH4  DOUB N N 66 
SIH CH4 OH5  SING N N 67 
SIH OH5 HOH5 SING N N 68 
# 
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 
SIH SMILES           ACDLabs              10.04 O=C(O)CCC(=O)OC3CC4(C(C2C3C1(C(=CC(=O)CC1)CC2)C)CCC4C(=O)C)C                                                                                                                                        
SIH InChI            InChI                1.02b InChI=1/C25H34O6/c1-14(26)18-6-7-19-17-5-4-15-12-16(27)10-11-24(15,2)23(17)20(13-25(18,19)3)31-22(30)9-8-21(28)29/h12,17-20,23H,4-11,13H2,1-3H3,(H,28,29)/t17-,18+,19-,20+,23+,24-,25+/m0/s1/f/h28H 
SIH InChIKey         InChI                1.02b JBBNFGYRYNBDIH-UAXCUTIUDC                                                                                                                                                                           
SIH SMILES_CANONICAL CACTVS               3.341 CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](C[C@]12C)OC(=O)CCC(O)=O                                                                                                                
SIH SMILES           CACTVS               3.341 CC(=O)[CH]1CC[CH]2[CH]3CCC4=CC(=O)CC[C]4(C)[CH]3[CH](C[C]12C)OC(=O)CCC(O)=O                                                                                                                         
SIH SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC(=O)[C@H]1CC[C@@H]2[C@@]1(C[C@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)OC(=O)CCC(=O)O)C                                                                                                                
SIH SMILES           "OpenEye OEToolkits" 1.5.0 CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)OC(=O)CCC(=O)O)C                                                                                                                                            
# 
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 
SIH "SYSTEMATIC NAME" ACDLabs              10.04 "4-{[(8alpha,11beta,14beta,17alpha)-3,20-dioxopregn-4-en-11-yl]oxy}-4-oxobutanoic acid"                                                                             
SIH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-[[(8S,9S,10R,11R,13S,14S,17S)-17-ethanoyl-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-11-yl]oxy]-4-oxo-butanoic acid" 
# 
