data_SMA
# 
_chem_comp.id                                    SMA 
_chem_comp.name                                  "STIGMATELLIN A" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C30 H42 O7" 
_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                        514.650 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     SMA 
_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        1KB9,1EZV 
_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 
SMA C2   C2   C 0 1 Y N N -17.286 37.727 -17.801 -0.406 -0.851 2.599   C2   SMA 1  
SMA C3   C3   C 0 1 Y N N -17.497 37.179 -19.032 -1.665 -0.471 2.878   C3   SMA 2  
SMA C3M  C3M  C 0 1 N N N -17.464 38.032 -20.291 -2.710 -0.458 1.793   C3M  SMA 3  
SMA C4   C4   C 0 1 Y N N -17.747 35.755 -19.198 -2.005 -0.083 4.202   C4   SMA 4  
SMA C4A  C4A  C 0 1 Y N N -17.763 34.955 -17.940 -0.934 -0.121 5.211   C4A  SMA 5  
SMA C5   C5   C 0 1 Y N N -18.038 33.513 -17.894 -1.172 0.242  6.543   C5   SMA 6  
SMA C5M  C5M  C 0 1 N N N -19.401 32.044 -19.076 -2.328 0.940  8.327   C5M  SMA 7  
SMA C6   C6   C 0 1 Y N N -18.029 32.835 -16.691 -0.137 0.192  7.458   C6   SMA 8  
SMA C7   C7   C 0 1 Y N N -17.785 33.530 -15.473 1.130  -0.216 7.059   C7   SMA 9  
SMA C7M  C7M  C 0 1 N N N -18.394 31.583 -14.265 1.589  0.161  9.217   C7M  SMA 10 
SMA C8   C8   C 0 1 Y N N -17.538 34.924 -15.449 1.374  -0.579 5.741   C8   SMA 11 
SMA C8A  C8A  C 0 1 Y N N -17.528 35.644 -16.648 0.347  -0.534 4.808   C8A  SMA 12 
SMA C9   C9   C 0 1 N N N -17.061 39.201 -17.594 -0.071 -1.258 1.187   C9   SMA 13 
SMA C10  C10  C 0 1 N N N -15.715 39.497 -17.072 0.383  -0.030 0.397   C10  SMA 14 
SMA C11  C11  C 0 1 N N S -15.404 40.974 -16.779 0.723  -0.443 -1.036  C11  SMA 15 
SMA C12  C12  C 0 1 N N R -14.110 41.336 -17.540 1.179  0.784  -1.826  C12  SMA 16 
SMA C13  C13  C 0 1 N N R -12.847 40.711 -16.743 1.400  0.396  -3.289  C13  SMA 17 
SMA C14  C14  C 0 1 N N S -11.620 41.660 -16.646 0.073  -0.058 -3.902  C14  SMA 18 
SMA C15  C15  C 0 1 N N N -10.307 40.910 -16.843 0.312  -0.552 -5.306  C15  SMA 19 
SMA C16  C16  C 0 1 N N N -9.098  41.290 -16.357 -0.299 0.036  -6.332  C16  SMA 20 
SMA C17  C17  C 0 1 N N N -8.219  40.532 -15.451 -0.068 -0.443 -7.697  C17  SMA 21 
SMA C18  C18  C 0 1 N N N -7.630  39.355 -15.768 -0.687 0.152  -8.736  C18  SMA 22 
SMA C19  C19  C 0 1 N N N -6.282  38.934 -15.401 -0.456 -0.327 -10.100 C19  SMA 23 
SMA C20  C20  C 0 1 N N N -5.597  39.308 -14.289 -1.068 0.261  -11.127 C20  SMA 24 
SMA C21  C21  C 0 1 N N N -4.192  38.832 -13.956 -0.830 -0.232 -12.531 C21  SMA 25 
SMA C22  C22  C 0 1 N N N -16.585 41.888 -17.117 1.846  -1.481 -1.014  C22  SMA 26 
SMA C23  C23  C 0 1 N N N -14.304 42.991 -19.047 2.231  2.686  -1.090  C23  SMA 27 
SMA C24  C24  C 0 1 N N N -13.212 40.287 -15.323 1.931  1.604  -4.063  C24  SMA 28 
SMA C25  C25  C 0 1 N N N -10.850 43.616 -15.645 -2.142 0.501  -3.703  C25  SMA 29 
SMA C26  C26  C 0 1 N N N -5.773  37.990 -16.472 0.474  -1.488 -10.343 C26  SMA 30 
SMA O1   O1   O 0 1 Y N N -17.310 36.993 -16.638 0.561  -0.888 3.522   O1   SMA 31 
SMA O4   O4   O 0 1 N N N -17.926 35.244 -20.314 -3.137 0.266  4.491   O4   SMA 32 
SMA O5   O5   O 0 1 N N N -18.271 32.835 -19.079 -2.410 0.641  6.932   O5   SMA 33 
SMA O7   O7   O 0 1 N N N -17.783 32.828 -14.261 2.139  -0.262 7.968   O7   SMA 34 
SMA O8   O8   O 0 1 N N N -17.308 35.549 -14.283 2.620  -0.979 5.365   O8   SMA 35 
SMA O12  O12  O 0 1 N N N -14.023 42.680 -17.749 2.401  1.279  -1.275  O12  SMA 36 
SMA O14  O14  O 0 1 N N N -11.843 43.009 -16.362 -0.838 1.040  -3.932  O14  SMA 37 
SMA H3M1 1H3M H 0 0 N N N -17.636 37.584 -21.297 -3.661 -0.124 2.208   H3M1 SMA 38 
SMA H3M2 2H3M H 0 0 N N N -18.186 38.870 -20.158 -2.402 0.222  0.999   H3M2 SMA 39 
SMA H3M3 3H3M H 0 0 N N N -16.488 38.571 -20.316 -2.824 -1.463 1.385   H3M3 SMA 40 
SMA H5M1 1H5M H 0 0 N N N -19.588 31.498 -20.030 -3.304 1.266  8.686   H5M1 SMA 41 
SMA H5M2 2H5M H 0 0 N N N -19.371 31.329 -18.220 -2.020 0.047  8.872   H5M2 SMA 42 
SMA H5M3 3H5M H 0 0 N N N -20.295 32.646 -18.792 -1.598 1.733  8.487   H5M3 SMA 43 
SMA H6   H6   H 0 1 N N N -18.215 31.747 -16.702 -0.314 0.471  8.486   H6   SMA 44 
SMA H7M1 1H7M H 0 0 N N N -18.392 31.024 -13.300 2.365  0.140  9.982   H7M1 SMA 45 
SMA H7M2 2H7M H 0 0 N N N -19.439 31.679 -14.640 1.202  1.175  9.119   H7M2 SMA 46 
SMA H7M3 3H7M H 0 0 N N N -17.947 30.948 -15.066 0.779  -0.510 9.504   H7M3 SMA 47 
SMA H91  1H9  H 0 1 N N N -17.264 39.773 -18.529 -0.954 -1.687 0.714   H91  SMA 48 
SMA H92  2H9  H 0 1 N N N -17.850 39.640 -16.940 0.728  -1.998 1.202   H92  SMA 49 
SMA H101 1H10 H 0 0 N N N -15.522 38.884 -16.160 1.266  0.399  0.870   H101 SMA 50 
SMA H102 2H10 H 0 0 N N N -14.944 39.080 -17.762 -0.416 0.709  0.382   H102 SMA 51 
SMA H11  H11  H 0 1 N N N -15.240 41.130 -15.687 -0.159 -0.872 -1.509  H11  SMA 52 
SMA H12  H12  H 0 1 N N N -14.117 40.887 -18.560 0.414  1.559  -1.767  H12  SMA 53 
SMA H13  H13  H 0 1 N N N -12.564 39.825 -17.359 2.123  -0.416 -3.344  H13  SMA 54 
SMA H14  H14  H 0 1 N N N -11.016 42.594 -16.726 -0.347 -0.863 -3.300  H14  SMA 55 
SMA H15  H15  H 0 1 N N N -10.220 39.968 -17.411 0.978  -1.384 -5.479  H15  SMA 56 
SMA H16  H16  H 0 1 N N N -8.808  42.288 -16.725 -0.966 0.868  -6.159  H16  SMA 57 
SMA H17  H17  H 0 1 N N N -7.977  40.880 -14.432 0.598  -1.275 -7.870  H17  SMA 58 
SMA H18  H18  H 0 1 N N N -8.288  38.698 -16.361 -1.354 0.984  -8.562  H18  SMA 59 
SMA H20  H20  H 0 1 N N N -6.181  39.997 -13.656 -1.735 1.093  -10.953 H20  SMA 60 
SMA H211 1H21 H 0 0 N N N -3.629  39.139 -13.043 -1.411 0.367  -13.231 H211 SMA 61 
SMA H212 2H21 H 0 0 N N N -4.212  37.717 -13.968 0.229  -0.146 -12.771 H212 SMA 62 
SMA H213 3H21 H 0 0 N N N -3.548  39.073 -14.833 -1.136 -1.275 -12.606 H213 SMA 63 
SMA H221 1H22 H 0 0 N N N -16.359 42.959 -16.904 2.698  -1.084 -0.462  H221 SMA 64 
SMA H222 2H22 H 0 0 N N N -16.916 41.746 -18.172 1.491  -2.391 -0.530  H222 SMA 65 
SMA H223 3H22 H 0 0 N N N -17.513 41.558 -16.594 2.150  -1.709 -2.036  H223 SMA 66 
SMA H231 1H23 H 0 0 N N N -14.232 44.090 -19.218 3.169  3.123  -0.745  H231 SMA 67 
SMA H232 2H23 H 0 0 N N N -13.658 42.421 -19.755 1.944  3.144  -2.036  H232 SMA 68 
SMA H233 3H23 H 0 0 N N N -15.295 42.589 -19.361 1.453  2.864  -0.349  H233 SMA 69 
SMA H241 1H24 H 0 0 N N N -12.342 39.856 -14.774 1.195  2.408  -4.033  H241 SMA 70 
SMA H242 2H24 H 0 0 N N N -13.669 41.130 -14.755 2.861  1.946  -3.609  H242 SMA 71 
SMA H243 3H24 H 0 0 N N N -14.077 39.583 -15.322 2.115  1.320  -5.099  H243 SMA 72 
SMA H251 1H25 H 0 0 N N N -11.028 44.693 -15.418 -2.866 1.314  -3.643  H251 SMA 73 
SMA H252 2H25 H 0 0 N N N -10.652 43.050 -14.704 -2.410 -0.164 -4.523  H252 SMA 74 
SMA H253 3H25 H 0 0 N N N -9.868  43.486 -16.158 -2.144 -0.056 -2.766  H253 SMA 75 
SMA H261 1H26 H 0 0 N N N -4.742  37.668 -16.191 0.519  -1.699 -11.411 H261 SMA 76 
SMA H262 2H26 H 0 0 N N N -6.459  37.129 -16.648 1.470  -1.236 -9.979  H262 SMA 77 
SMA H263 3H26 H 0 0 N N N -5.821  38.432 -17.494 0.104  -2.366 -9.814  H263 SMA 78 
SMA HO8  HO8  H 0 1 N N N -17.142 36.484 -14.266 2.656  -1.937 5.488   HO8  SMA 79 
# 
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 
SMA C2  C3   DOUB Y N 1  
SMA C2  C9   SING N N 2  
SMA C2  O1   SING Y N 3  
SMA C3  C3M  SING N N 4  
SMA C3  C4   SING Y N 5  
SMA C3M H3M1 SING N N 6  
SMA C3M H3M2 SING N N 7  
SMA C3M H3M3 SING N N 8  
SMA C4  C4A  SING Y N 9  
SMA C4  O4   DOUB N N 10 
SMA C4A C5   SING Y N 11 
SMA C4A C8A  DOUB Y N 12 
SMA C5  C6   DOUB Y N 13 
SMA C5  O5   SING N N 14 
SMA C5M O5   SING N N 15 
SMA C5M H5M1 SING N N 16 
SMA C5M H5M2 SING N N 17 
SMA C5M H5M3 SING N N 18 
SMA C6  C7   SING Y N 19 
SMA C6  H6   SING N N 20 
SMA C7  C8   DOUB Y N 21 
SMA C7  O7   SING N N 22 
SMA C7M O7   SING N N 23 
SMA C7M H7M1 SING N N 24 
SMA C7M H7M2 SING N N 25 
SMA C7M H7M3 SING N N 26 
SMA C8  C8A  SING Y N 27 
SMA C8  O8   SING N N 28 
SMA C8A O1   SING Y N 29 
SMA C9  C10  SING N N 30 
SMA C9  H91  SING N N 31 
SMA C9  H92  SING N N 32 
SMA C10 C11  SING N N 33 
SMA C10 H101 SING N N 34 
SMA C10 H102 SING N N 35 
SMA C11 C12  SING N N 36 
SMA C11 C22  SING N N 37 
SMA C11 H11  SING N N 38 
SMA C12 C13  SING N N 39 
SMA C12 O12  SING N N 40 
SMA C12 H12  SING N N 41 
SMA C13 C14  SING N N 42 
SMA C13 C24  SING N N 43 
SMA C13 H13  SING N N 44 
SMA C14 C15  SING N N 45 
SMA C14 O14  SING N N 46 
SMA C14 H14  SING N N 47 
SMA C15 C16  DOUB N E 48 
SMA C15 H15  SING N N 49 
SMA C16 C17  SING N N 50 
SMA C16 H16  SING N N 51 
SMA C17 C18  DOUB N E 52 
SMA C17 H17  SING N N 53 
SMA C18 C19  SING N N 54 
SMA C18 H18  SING N N 55 
SMA C19 C20  DOUB N E 56 
SMA C19 C26  SING N N 57 
SMA C20 C21  SING N N 58 
SMA C20 H20  SING N N 59 
SMA C21 H211 SING N N 60 
SMA C21 H212 SING N N 61 
SMA C21 H213 SING N N 62 
SMA C22 H221 SING N N 63 
SMA C22 H222 SING N N 64 
SMA C22 H223 SING N N 65 
SMA C23 O12  SING N N 66 
SMA C23 H231 SING N N 67 
SMA C23 H232 SING N N 68 
SMA C23 H233 SING N N 69 
SMA C24 H241 SING N N 70 
SMA C24 H242 SING N N 71 
SMA C24 H243 SING N N 72 
SMA C25 O14  SING N N 73 
SMA C25 H251 SING N N 74 
SMA C25 H252 SING N N 75 
SMA C25 H253 SING N N 76 
SMA C26 H261 SING N N 77 
SMA C26 H262 SING N N 78 
SMA C26 H263 SING N N 79 
SMA O8  HO8  SING N N 80 
# 
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 
SMA SMILES           ACDLabs              10.04 O=C1c2c(OC(=C1C)CCC(C)C(OC)C(C)C(OC)\C=C\C=C\C(=C\C)C)c(O)c(OC)cc2OC 
SMA InChI            InChI                1.02b 
InChI=1/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29+/m0/s1 
SMA InChIKey         InChI                1.02b UZHDGDDPOPDJGM-UBAANNQEBK 
SMA SMILES_CANONICAL CACTVS               3.341 CO[C@@H](\C=C\C=C\C(C)=C\C)[C@@H](C)[C@H](OC)[C@@H](C)CCC1=C(C)C(=O)c2c(OC)cc(OC)c(O)c2O1 
SMA SMILES           CACTVS               3.341 CO[CH](C=CC=CC(C)=CC)[CH](C)[CH](OC)[CH](C)CCC1=C(C)C(=O)c2c(OC)cc(OC)c(O)c2O1 
SMA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C\C=C(/C)\C=CC=CC([C@@H](C)[C@@H]([C@@H](C)CCC1=C(C(=O)c2c(cc(c(c2O1)O)OC)OC)C)OC)OC 
SMA SMILES           "OpenEye OEToolkits" 1.5.0 CC=C(C)C=CC=CC(C(C)C(C(C)CCC1=C(C(=O)c2c(cc(c(c2O1)O)OC)OC)C)OC)OC 
# 
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 
SMA "SYSTEMATIC NAME" ACDLabs              10.04 2-[(3S,4R,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methyl-4H-chromen-4-one 
SMA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 2-[(3S,4R,5S,11E)-4,6-dimethoxy-3,5,11-trimethyl-trideca-7,9,11-trienyl]-8-hydroxy-5,7-dimethoxy-3-methyl-chromen-4-one               
# 
