data_GA4
# 
_chem_comp.id                                    GA4 
_chem_comp.name                                  "GIBBERELLIN A4" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H24 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2001-11-26 
_chem_comp.pdbx_modified_date                    2008-12-05 
_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                        332.391 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GA4 
_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        ? 
_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 
GA4 C1   C1   C 0 1 N N N 50.429 24.076 -2.453 -1.212 1.858  1.486  C1   GA4 1  
GA4 C2   C2   C 0 1 N N N 49.734 24.510 -1.161 -1.459 1.227  2.866  C2   GA4 2  
GA4 C3   C3   C 0 1 N N S 50.567 25.433 -0.226 -0.279 0.368  3.323  C3   GA4 3  
GA4 O31  O31  O 0 1 N N N 50.325 26.761 -0.665 0.851  1.203  3.578  O31  GA4 4  
GA4 C4   C4   C 0 1 N N S 52.138 25.114 -0.228 0.068  -0.653 2.202  C4   GA4 5  
GA4 C5   C5   C 0 1 N N R 52.634 25.079 -1.713 0.606  0.237  1.068  C5   GA4 6  
GA4 C6   C6   C 0 1 N N S 54.142 24.891 -2.003 1.216  -0.499 -0.120 C6   GA4 7  
GA4 C7   C7   C 0 1 N N N 54.786 26.206 -2.364 2.619  -0.011 -0.372 C7   GA4 8  
GA4 O71  O71  O 0 1 N N N 54.411 27.091 -3.140 2.888  0.545  -1.411 O71  GA4 9  
GA4 O72  O72  O 0 1 N N N 55.965 26.427 -1.714 3.571  -0.194 0.556  O72  GA4 10 
GA4 C8   C8   C 0 1 N N R 54.262 23.796 -3.112 0.324  -0.177 -1.311 C8   GA4 11 
GA4 C9   C9   C 0 1 N N R 52.754 23.365 -3.437 -0.432 1.109  -0.890 C9   GA4 12 
GA4 C10  C10  C 0 1 N N R 51.931 23.800 -2.220 -0.775 0.773  0.533  C10  GA4 13 
GA4 C11  C11  C 0 1 N N N 52.544 21.850 -3.731 -1.500 1.493  -1.859 C11  GA4 14 
GA4 C12  C12  C 0 1 N N N 53.773 21.046 -4.172 -2.258 0.332  -2.484 C12  GA4 15 
GA4 C13  C13  C 0 1 N N R 55.131 21.722 -3.884 -1.304 -0.799 -2.885 C13  GA4 16 
GA4 C14  C14  C 0 1 N N N 55.083 22.572 -2.598 -0.686 -1.301 -1.548 C14  GA4 17 
GA4 C15  C15  C 0 1 N N N 54.994 24.104 -4.457 0.969  0.052  -2.664 C15  GA4 18 
GA4 C16  C16  C 0 1 N N N 55.521 22.756 -4.918 -0.129 -0.251 -3.676 C16  GA4 19 
GA4 C17  C17  C 0 1 N N N 56.213 22.534 -6.028 -0.061 -0.071 -4.972 C17  GA4 20 
GA4 C18  C18  C 0 1 N N N 52.876 26.064 0.700  1.021  -1.768 2.636  C18  GA4 21 
GA4 C19  C19  C 0 1 N N N 52.266 23.618 0.114  -1.287 -1.142 1.703  C19  GA4 22 
GA4 O91  O91  O 0 1 N N N 52.445 22.999 1.154  -1.948 -2.032 2.183  O91  GA4 23 
GA4 O92  O92  O 0 1 N N N 52.127 22.863 -1.070 -1.630 -0.402 0.619  O92  GA4 24 
GA4 H11  1H1  H 0 1 N N N 49.919 23.199 -2.916 -2.132 2.316  1.122  H11  GA4 25 
GA4 H12  2H1  H 0 1 N N N 50.271 24.817 -3.270 -0.430 2.613  1.564  H12  GA4 26 
GA4 H21  1H2  H 0 1 N N N 48.756 24.990 -1.397 -2.353 0.605  2.816  H21  GA4 27 
GA4 H22  2H2  H 0 1 N N N 49.383 23.613 -0.597 -1.623 2.021  3.594  H22  GA4 28 
GA4 H3   H3   H 0 1 N N N 50.249 25.267 0.829  -0.549 -0.167 4.233  H3   GA4 29 
GA4 HO3  HO3  H 0 1 N N N 50.833 27.324 -0.094 0.592  1.819  4.277  HO3  GA4 30 
GA4 H5   H5   H 0 1 N N N 52.417 26.070 -2.175 1.246  1.042  1.429  H5   GA4 31 
GA4 H6   H6   H 0 1 N N N 54.699 24.544 -1.101 1.219  -1.572 0.069  H6   GA4 32 
GA4 HO7  HO7  H 0 1 N N N 56.370 27.255 -1.941 4.471  0.118  0.394  HO7  GA4 33 
GA4 H9   H9   H 0 1 N N N 52.437 23.857 -4.385 0.299  1.917  -0.867 H9   GA4 34 
GA4 H111 1H11 H 0 0 N N N 52.079 21.360 -2.843 -2.217 2.132  -1.342 H111 GA4 35 
GA4 H112 2H11 H 0 0 N N N 51.730 21.727 -4.484 -1.044 2.075  -2.659 H112 GA4 36 
GA4 H121 1H12 H 0 0 N N N 53.747 20.025 -3.722 -2.983 -0.049 -1.765 H121 GA4 37 
GA4 H122 2H12 H 0 0 N N N 53.694 20.784 -5.253 -2.785 0.685  -3.370 H122 GA4 38 
GA4 H13  H13  H 0 1 N N N 55.837 20.860 -3.845 -1.820 -1.594 -3.422 H13  GA4 39 
GA4 H141 1H14 H 0 0 N N N 56.069 22.808 -2.134 -1.432 -1.340 -0.754 H141 GA4 40 
GA4 H142 2H14 H 0 0 N N N 54.679 22.061 -1.692 -0.193 -2.265 -1.675 H142 GA4 41 
GA4 H151 1H15 H 0 0 N N N 54.360 24.627 -5.210 1.290  1.089  -2.762 H151 GA4 42 
GA4 H152 2H15 H 0 0 N N N 55.774 24.896 -4.379 1.813  -0.623 -2.804 H152 GA4 43 
GA4 H171 1H17 H 0 0 N N N 56.595 21.555 -6.362 0.838  0.329  -5.415 H171 GA4 44 
GA4 H172 2H17 H 0 0 N N N 56.497 23.287 -6.781 -0.905 -0.323 -5.597 H172 GA4 45 
GA4 H181 1H18 H 0 0 N N N 53.968 25.842 0.698  0.577  -2.326 3.460  H181 GA4 46 
GA4 H182 2H18 H 0 0 N N N 52.669 27.130 0.450  1.200  -2.441 1.797  H182 GA4 47 
GA4 H183 3H18 H 0 0 N N N 52.451 26.049 1.730  1.967  -1.333 2.960  H183 GA4 48 
# 
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 
GA4 C1  C2   SING N N 1  
GA4 C1  C10  SING N N 2  
GA4 C1  H11  SING N N 3  
GA4 C1  H12  SING N N 4  
GA4 C2  C3   SING N N 5  
GA4 C2  H21  SING N N 6  
GA4 C2  H22  SING N N 7  
GA4 C3  O31  SING N N 8  
GA4 C3  C4   SING N N 9  
GA4 C3  H3   SING N N 10 
GA4 O31 HO3  SING N N 11 
GA4 C4  C5   SING N N 12 
GA4 C4  C18  SING N N 13 
GA4 C4  C19  SING N N 14 
GA4 C5  C6   SING N N 15 
GA4 C5  C10  SING N N 16 
GA4 C5  H5   SING N N 17 
GA4 C6  C7   SING N N 18 
GA4 C6  C8   SING N N 19 
GA4 C6  H6   SING N N 20 
GA4 C7  O71  DOUB N N 21 
GA4 C7  O72  SING N N 22 
GA4 O72 HO7  SING N N 23 
GA4 C8  C9   SING N N 24 
GA4 C8  C14  SING N N 25 
GA4 C8  C15  SING N N 26 
GA4 C9  C10  SING N N 27 
GA4 C9  C11  SING N N 28 
GA4 C9  H9   SING N N 29 
GA4 C10 O92  SING N N 30 
GA4 C11 C12  SING N N 31 
GA4 C11 H111 SING N N 32 
GA4 C11 H112 SING N N 33 
GA4 C12 C13  SING N N 34 
GA4 C12 H121 SING N N 35 
GA4 C12 H122 SING N N 36 
GA4 C13 C14  SING N N 37 
GA4 C13 C16  SING N N 38 
GA4 C13 H13  SING N N 39 
GA4 C14 H141 SING N N 40 
GA4 C14 H142 SING N N 41 
GA4 C15 C16  SING N N 42 
GA4 C15 H151 SING N N 43 
GA4 C15 H152 SING N N 44 
GA4 C16 C17  DOUB N N 45 
GA4 C17 H171 SING N N 46 
GA4 C17 H172 SING N N 47 
GA4 C18 H181 SING N N 48 
GA4 C18 H182 SING N N 49 
GA4 C18 H183 SING N N 50 
GA4 C19 O91  DOUB N N 51 
GA4 C19 O92  SING N N 52 
# 
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 
GA4 SMILES           ACDLabs              10.04 O=C(O)C4C21CC(\C(=C)C1)CCC2C35OC(=O)C(C)(C34)C(O)CC5                                                                                                                          
GA4 InChI            InChI                1.02b InChI=1/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11-,12+,13-,14-,17-,18+,19-/m1/s1/f/h21H 
GA4 InChIKey         InChI                1.02b RSQSQJNRHICNNH-UIEGTMJDDR                                                                                                                                                     
GA4 SMILES_CANONICAL CACTVS               3.341 C[C@]12[C@@H](O)CC[C@@]3(OC1=O)[C@@H]4CC[C@@H]5C[C@]4(CC5=C)[C@H]([C@H]23)C(O)=O                                                                                              
GA4 SMILES           CACTVS               3.341 C[C]12[CH](O)CC[C]3(OC1=O)[CH]4CC[CH]5C[C]4(CC5=C)[CH]([CH]23)C(O)=O                                                                                                          
GA4 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@@]12[C@H](CC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@H](C4)C(=C)C5)C(=O)O)OC2=O)O                                                                                            
GA4 SMILES           "OpenEye OEToolkits" 1.5.0 CC12C(CCC3(C1C(C45C3CCC(C4)C(=C)C5)C(=O)O)OC2=O)O                                                                                                                             
# 
_pdbx_chem_comp_identifier.comp_id           GA4 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           ACDLabs 
_pdbx_chem_comp_identifier.program_version   10.04 
_pdbx_chem_comp_identifier.identifier        "(1S,2S,4aR,4bR,7R,9aR,10S,10aR)-2-hydroxy-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid" 
# 
