data_AJA
# 
_chem_comp.id                                    AJA 
_chem_comp.name                                  "(6AR,10AR)-3-(1,1-DIMETHYLHEPTYL)-1-HYDROXY-6,6-DIMETHYL-6A,7,10,10A-TETRAHYDRO-6H-BENZO[C]CHROMENE-9-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H36 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         
;AJULEMIC ACID; CT-3; IP-751; 1',1'-DIMETHYLHEPTYL-DELTA8-TETRAHYDROCANNABINOL-11-OIC ACID
;
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2007-02-02 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        400.551 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AJA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye/OEToolkits V1.4.2" 
_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 
AJA O27  O27  O 0 1 N N N 16.688 -8.185  -44.947 5.920  5.108  -5.952 O27  AJA 1  
AJA C16  C16  C 0 1 N N N 17.269 -7.270  -44.324 5.201  4.863  -5.000 C16  AJA 2  
AJA O26  O26  O 0 1 N N N 16.760 -6.137  -44.183 5.454  5.182  -3.714 O26  AJA 3  
AJA C10  C10  C 0 1 N N N 18.582 -7.533  -43.742 3.915  4.166  -5.089 C10  AJA 4  
AJA C9   C9   C 0 1 N N N 18.884 -8.884  -43.138 3.475  3.323  -3.929 C9   AJA 5  
AJA C8   C8   C 0 1 N N R 20.385 -9.011  -42.905 2.311  2.368  -4.287 C8   AJA 6  
AJA C7   C7   C 0 1 Y N N 20.737 -10.441 -42.749 1.667  1.709  -3.087 C7   AJA 7  
AJA C6   C6   C 0 1 Y N N 19.858 -11.282 -42.087 2.445  1.195  -2.036 C6   AJA 8  
AJA O15  O15  O 0 1 N N N 18.690 -10.787 -41.591 3.809  1.193  -2.057 O15  AJA 9  
AJA C5   C5   C 0 1 Y N N 20.163 -12.628 -41.926 1.850  0.586  -0.930 C5   AJA 10 
AJA C4   C4   C 0 1 Y N N 21.354 -13.133 -42.431 0.466  0.471  -0.861 C4   AJA 11 
AJA C19  C19  C 0 1 N N N 21.689 -14.585 -42.261 -0.174 -0.177 0.320  C19  AJA 12 
AJA C25  C25  C 0 1 N N N 20.409 -15.402 -42.399 0.812  -0.677 1.432  C25  AJA 13 
AJA C20  C20  C 0 1 N N N 22.296 -14.788 -40.878 -1.237 0.752  1.032  C20  AJA 14 
AJA C21  C21  C 0 1 N N N 23.435 -13.805 -40.632 -0.654 2.051  1.610  C21  AJA 15 
AJA C22  C22  C 0 1 N N N 24.104 -14.070 -39.289 -1.697 2.910  2.335  C22  AJA 16 
AJA C23  C23  C 0 1 N N N 25.622 -14.065 -39.424 -1.129 4.217  2.892  C23  AJA 17 
AJA C28  C28  C 0 1 N N N 26.278 -13.446 -38.196 -2.211 5.036  3.596  C28  AJA 18 
AJA C29  C29  C 0 1 N N N 27.784 -13.417 -38.342 -1.660 6.351  4.124  C29  AJA 19 
AJA C24  C24  C 0 1 N N N 22.688 -14.986 -43.339 -0.945 -1.464 -0.128 C24  AJA 20 
AJA C3   C3   C 0 1 Y N N 22.235 -12.289 -43.095 -0.320 0.950  -1.905 C3   AJA 21 
AJA C2   C2   C 0 1 Y N N 21.928 -10.942 -43.255 0.276  1.550  -3.020 C2   AJA 22 
AJA O1   O1   O 0 1 N N N 22.814 -10.130 -43.914 -0.594 1.962  -3.994 O1   AJA 23 
AJA C14  C14  C 0 1 N N N 22.653 -8.714  -43.909 -0.035 2.292  -5.283 C14  AJA 24 
AJA C18  C18  C 0 1 N N N 23.181 -8.165  -42.589 -1.134 2.953  -6.134 C18  AJA 25 
AJA C17  C17  C 0 1 N N N 23.436 -8.127  -45.077 0.294  0.935  -5.928 C17  AJA 26 
AJA C13  C13  C 0 1 N N R 21.171 -8.401  -44.057 1.251  3.139  -5.106 C13  AJA 27 
AJA C12  C12  C 0 1 N N N 20.941 -6.896  -44.143 1.869  3.659  -6.420 C12  AJA 28 
AJA C11  C11  C 0 1 N N N 19.520 -6.576  -43.744 3.210  4.306  -6.220 C11  AJA 29 
AJA HO26 HO26 H 0 0 N N N 15.912 -6.115  -44.610 6.310  5.651  -3.615 HO26 AJA 30 
AJA H91  1H9  H 0 1 N N N 18.354 -8.984  -42.179 4.350  2.749  -3.610 H91  AJA 31 
AJA H92  2H9  H 0 1 N N N 18.551 -9.676  -43.825 3.191  3.982  -3.099 H92  AJA 32 
AJA H8   H8   H 0 1 N N N 20.648 -8.462  -41.989 2.720  1.560  -4.911 H8   AJA 33 
AJA HO15 HO15 H 0 0 N N N 18.768 -10.672 -40.651 4.156  1.205  -1.152 HO15 AJA 34 
AJA H5   H5   H 0 1 N N N 19.475 -13.280 -41.409 2.469  0.192  -0.127 H5   AJA 35 
AJA H251 1H25 H 0 0 N N N 19.990 -15.599 -41.401 1.439  0.137  1.810  H251 AJA 36 
AJA H252 2H25 H 0 0 N N N 19.678 -14.840 -42.999 1.482  -1.450 1.035  H252 AJA 37 
AJA H253 3H25 H 0 0 N N N 20.636 -16.357 -42.896 0.292  -1.114 2.293  H253 AJA 38 
AJA H201 1H20 H 0 0 N N N 21.516 -14.629 -40.118 -2.024 1.001  0.311  H201 AJA 39 
AJA H202 2H20 H 0 0 N N N 22.695 -15.811 -40.816 -1.742 0.209  1.843  H202 AJA 40 
AJA H211 1H21 H 0 0 N N N 24.182 -13.916 -41.432 0.131  1.809  2.335  H211 AJA 41 
AJA H212 2H21 H 0 0 N N N 23.023 -12.785 -40.624 -0.185 2.648  0.820  H212 AJA 42 
AJA H221 1H22 H 0 0 N N N 23.806 -13.284 -38.580 -2.108 2.319  3.163  H221 AJA 43 
AJA H222 2H22 H 0 0 N N N 23.787 -15.060 -38.928 -2.533 3.126  1.658  H222 AJA 44 
AJA H231 1H23 H 0 0 N N N 25.974 -15.101 -39.533 -0.320 3.995  3.598  H231 AJA 45 
AJA H232 2H23 H 0 0 N N N 25.894 -13.467 -40.306 -0.698 4.817  2.083  H232 AJA 46 
AJA H281 1H28 H 0 0 N N N 25.911 -12.416 -38.075 -3.033 5.244  2.900  H281 AJA 47 
AJA H282 2H28 H 0 0 N N N 26.022 -14.055 -37.317 -2.630 4.461  4.431  H282 AJA 48 
AJA H291 1H29 H 0 0 N N N 28.049 -13.410 -39.409 -2.450 6.919  4.626  H291 AJA 49 
AJA H292 2H29 H 0 0 N N N 28.182 -12.512 -37.860 -0.856 6.177  4.847  H292 AJA 50 
AJA H293 3H29 H 0 0 N N N 28.216 -14.308 -37.863 -1.264 6.966  3.310  H293 AJA 51 
AJA H241 1H24 H 0 0 N N N 22.168 -15.083 -44.304 -1.754 -1.223 -0.825 H241 AJA 52 
AJA H242 2H24 H 0 0 N N N 23.469 -14.216 -43.419 -0.265 -2.155 -0.640 H242 AJA 53 
AJA H243 3H24 H 0 0 N N N 23.148 -15.949 -43.072 -1.396 -2.003 0.714  H243 AJA 54 
AJA H3   H3   H 0 1 N N N 23.162 -12.680 -43.488 -1.403 0.849  -1.859 H3   AJA 55 
AJA H181 1H18 H 0 0 N N N 23.308 -8.990  -41.873 -1.974 2.266  -6.277 H181 AJA 56 
AJA H182 2H18 H 0 0 N N N 24.151 -7.674  -42.758 -1.507 3.858  -5.646 H182 AJA 57 
AJA H183 3H18 H 0 0 N N N 22.465 -7.435  -42.183 -0.744 3.228  -7.119 H183 AJA 58 
AJA H171 1H17 H 0 0 N N N 22.763 -7.986  -45.936 -0.552 0.577  -6.523 H171 AJA 59 
AJA H172 2H17 H 0 0 N N N 23.862 -7.157  -44.782 1.165  1.022  -6.585 H172 AJA 60 
AJA H173 3H17 H 0 0 N N N 24.248 -8.815  -45.357 0.514  0.188  -5.160 H173 AJA 61 
AJA H13  H13  H 0 1 N N N 20.810 -8.848  -44.995 0.967  4.020  -4.506 H13  AJA 62 
AJA H121 1H12 H 0 0 N N N 21.636 -6.380  -43.464 1.199  4.401  -6.869 H121 AJA 63 
AJA H122 2H12 H 0 0 N N N 21.115 -6.559  -45.175 1.992  2.850  -7.148 H122 AJA 64 
AJA H11  H11  H 0 1 N N N 19.258 -5.568  -43.458 3.588  4.907  -7.043 H11  AJA 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 
AJA O27 C16  DOUB N N 1  
AJA C16 O26  SING N N 2  
AJA C16 C10  SING N N 3  
AJA O26 HO26 SING N N 4  
AJA C10 C11  DOUB N N 5  
AJA C10 C9   SING N N 6  
AJA C9  C8   SING N N 7  
AJA C9  H91  SING N N 8  
AJA C9  H92  SING N N 9  
AJA C8  C13  SING N N 10 
AJA C8  C7   SING N N 11 
AJA C8  H8   SING N N 12 
AJA C7  C2   SING Y N 13 
AJA C7  C6   DOUB Y N 14 
AJA C6  C5   SING Y N 15 
AJA C6  O15  SING N N 16 
AJA O15 HO15 SING N N 17 
AJA C5  C4   DOUB Y N 18 
AJA C5  H5   SING N N 19 
AJA C4  C3   SING Y N 20 
AJA C4  C19  SING N N 21 
AJA C19 C24  SING N N 22 
AJA C19 C25  SING N N 23 
AJA C19 C20  SING N N 24 
AJA C25 H251 SING N N 25 
AJA C25 H252 SING N N 26 
AJA C25 H253 SING N N 27 
AJA C20 C21  SING N N 28 
AJA C20 H201 SING N N 29 
AJA C20 H202 SING N N 30 
AJA C21 C22  SING N N 31 
AJA C21 H211 SING N N 32 
AJA C21 H212 SING N N 33 
AJA C22 C23  SING N N 34 
AJA C22 H221 SING N N 35 
AJA C22 H222 SING N N 36 
AJA C23 C28  SING N N 37 
AJA C23 H231 SING N N 38 
AJA C23 H232 SING N N 39 
AJA C28 C29  SING N N 40 
AJA C28 H281 SING N N 41 
AJA C28 H282 SING N N 42 
AJA C29 H291 SING N N 43 
AJA C29 H292 SING N N 44 
AJA C29 H293 SING N N 45 
AJA C24 H241 SING N N 46 
AJA C24 H242 SING N N 47 
AJA C24 H243 SING N N 48 
AJA C3  C2   DOUB Y N 49 
AJA C3  H3   SING N N 50 
AJA C2  O1   SING N N 51 
AJA O1  C14  SING N N 52 
AJA C14 C17  SING N N 53 
AJA C14 C13  SING N N 54 
AJA C14 C18  SING N N 55 
AJA C18 H181 SING N N 56 
AJA C18 H182 SING N N 57 
AJA C18 H183 SING N N 58 
AJA C17 H171 SING N N 59 
AJA C17 H172 SING N N 60 
AJA C17 H173 SING N N 61 
AJA C13 C12  SING N N 62 
AJA C13 H13  SING N N 63 
AJA C12 C11  SING N N 64 
AJA C12 H121 SING N N 65 
AJA C12 H122 SING N N 66 
AJA C11 H11  SING N N 67 
# 
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 
AJA SMILES           ACDLabs              10.04 O=C(O)C3=CCC1C(c2c(OC1(C)C)cc(cc2O)C(C)(C)CCCCCC)C3                                                                                                                            
AJA InChI            InChI                1.02b InChI=1/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1/f/h27H 
AJA InChIKey         InChI                1.02b YCHYFHOSGQABSW-DTOKZBNUDR                                                                                                                                                      
AJA SMILES_CANONICAL CACTVS               3.341 CCCCCCC(C)(C)c1cc(O)c2[C@@H]3CC(=CC[C@H]3C(C)(C)Oc2c1)C(O)=O                                                                                                                   
AJA SMILES           CACTVS               3.341 CCCCCCC(C)(C)c1cc(O)c2[CH]3CC(=CC[CH]3C(C)(C)Oc2c1)C(O)=O                                                                                                                      
AJA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCCCC(C)(C)c1cc(c2c(c1)OC([C@H]3[C@H]2CC(=CC3)C(=O)O)(C)C)O                                                                                                                  
AJA SMILES           "OpenEye OEToolkits" 1.5.0 CCCCCCC(C)(C)c1cc(c2c(c1)OC(C3C2CC(=CC3)C(=O)O)(C)C)O                                                                                                                          
# 
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 
AJA "SYSTEMATIC NAME" ACDLabs              10.04 "(6aR,10aR)-3-(1,1-dimethylheptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid" 
AJA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid"     
# 
