data_LAR
# 
_chem_comp.id                                    LAR 
_chem_comp.name                                  "LATRUNCULIN A" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H31 N O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         4-(17-HYDROXY-5,12-DIMETHYL-3-OXO-2,16-DIOXABICYCLO[13.3.1]NONADECA-4,8,10-TRIEN-17-YL)-2-THIAZOLIDINONE 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2000-04-13 
_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                        421.550 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     LAR 
_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        1ESV 
_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 
LAR S1   S1   S 0 1 N N N 20.246 10.112 81.204 4.971  -0.004 -1.617 S1   LAR 1  
LAR N1   N1   N 0 1 N N N 20.159 8.684  79.108 4.140  -1.165 0.436  N1   LAR 2  
LAR O1   O1   O 0 1 N N N 18.556 10.321 74.908 -2.425 -1.191 1.508  O1   LAR 3  
LAR O2   O2   O 0 1 N N N 16.586 10.009 75.984 -0.325 -1.506 0.880  O2   LAR 4  
LAR O3   O3   O 0 1 N N N 16.538 8.351  79.185 1.647  1.465  0.961  O3   LAR 5  
LAR O4   O4   O 0 1 N N N 17.690 10.332 78.857 1.573  -0.381 -0.450 O4   LAR 6  
LAR O5   O5   O 0 1 N N N 22.116 9.872  79.355 5.303  -2.589 -0.927 O5   LAR 7  
LAR C1   C1   C 0 1 N N N 17.432 10.715 75.210 -1.643 -1.757 0.770  C1   LAR 8  
LAR C2   C2   C 0 1 N N N 16.850 12.006 74.827 -2.150 -2.703 -0.228 C2   LAR 9  
LAR C3   C3   C 0 1 N N N 15.855 12.721 75.366 -3.450 -2.870 -0.452 C3   LAR 10 
LAR C4   C4   C 0 1 N N N 15.106 12.301 76.594 -4.493 -2.081 0.291  C4   LAR 11 
LAR C5   C5   C 0 1 N N N 13.654 12.559 76.368 -5.298 -1.240 -0.706 C5   LAR 12 
LAR C6   C6   C 0 1 N N N 12.760 11.918 77.371 -4.863 0.199  -0.566 C6   LAR 13 
LAR C7   C7   C 0 1 N N N 13.022 11.214 78.478 -3.775 0.629  -1.183 C7   LAR 14 
LAR C8   C8   C 0 1 N N N 11.975 10.664 79.282 -3.303 2.014  -1.050 C8   LAR 15 
LAR C9   C9   C 0 1 N N N 12.245 10.005 80.427 -2.005 2.262  -1.177 C9   LAR 16 
LAR C10  C10  C 0 1 N N S 13.649 9.690  80.857 -1.464 3.659  -1.022 C10  LAR 17 
LAR C11  C11  C 0 1 N N N 14.093 8.306  80.468 -0.114 3.595  -0.301 C11  LAR 18 
LAR C12  C12  C 0 1 N N N 14.182 8.083  78.979 -0.287 2.891  1.048  C12  LAR 19 
LAR C13  C13  C 0 1 N N R 15.387 8.676  78.306 0.222  1.445  0.928  C13  LAR 20 
LAR C14  C14  C 0 1 N N N 15.615 8.099  76.932 -0.327 0.629  2.098  C14  LAR 21 
LAR C15  C15  C 0 1 N N R 16.919 8.624  76.378 0.210  -0.794 2.022  C15  LAR 22 
LAR C16  C16  C 0 1 N N N 18.093 8.564  77.318 1.740  -0.745 1.934  C16  LAR 23 
LAR C17  C17  C 0 1 N N R 17.761 8.913  78.765 2.134  0.147  0.753  C17  LAR 24 
LAR C18  C18  C 0 1 N N R 18.810 8.385  79.717 3.659  0.183  0.629  C18  LAR 25 
LAR C19  C19  C 0 1 N N N 18.841 8.920  81.124 4.040  1.135  -0.523 C19  LAR 26 
LAR C20  C20  C 0 1 N N N 21.006 9.512  79.691 4.845  -1.496 -0.652 C20  LAR 27 
LAR C21  C21  C 0 1 N N N 15.457 14.053 74.681 -3.897 -3.867 -1.498 C21  LAR 28 
LAR C22  C22  C 0 1 N N N 13.800 9.983  82.427 -2.443 4.500  -0.201 C22  LAR 29 
LAR HN1  HN1  H 0 1 N N N 20.525 8.297  78.237 3.951  -1.839 1.107  HN1  LAR 30 
LAR HO4  HO4  H 0 1 N N N 18.514 10.710 78.574 1.877  -1.296 -0.522 HO4  LAR 31 
LAR H21  1H2  H 0 1 N N N 17.241 12.552 73.952 -1.456 -3.287 -0.827 H21  LAR 32 
LAR H41  1H4  H 0 1 N N N 15.314 11.244 76.883 -5.162 -2.765 0.814  H41  LAR 33 
LAR H42  2H4  H 0 1 N N N 15.490 12.790 77.519 -4.007 -1.424 1.012  H42  LAR 34 
LAR H51  1H5  H 0 1 N N N 13.455 13.654 76.311 -5.103 -1.586 -1.721 H51  LAR 35 
LAR H52  2H5  H 0 1 N N N 13.360 12.260 75.334 -6.362 -1.326 -0.486 H52  LAR 36 
LAR H61  1H6  H 0 1 N N N 11.663 11.977 77.272 -5.425 0.859  0.066  H61  LAR 37 
LAR H71  1H7  H 0 1 N N N 14.089 11.088 78.725 -3.213 -0.053 -1.823 H71  LAR 38 
LAR H81  1H8  H 0 1 N N N 10.910 10.752 79.006 -4.010 2.812  -0.884 H81  LAR 39 
LAR H91  1H9  H 0 1 N N N 11.341 9.730  80.996 -1.333 1.445  -1.383 H91  LAR 40 
LAR H101 1H10 H 0 0 N N N 14.345 10.362 80.303 -1.331 4.109  -2.005 H101 LAR 41 
LAR H111 1H11 H 0 0 N N N 15.061 8.053  80.959 0.598  3.039  -0.912 H111 LAR 42 
LAR H112 2H11 H 0 0 N N N 13.436 7.538  80.939 0.259  4.606  -0.138 H112 LAR 43 
LAR H121 1H12 H 0 0 N N N 14.116 6.993  78.752 0.288  3.417  1.811  H121 LAR 44 
LAR H122 2H12 H 0 0 N N N 13.251 8.445  78.482 -1.341 2.885  1.324  H122 LAR 45 
LAR H131 1H13 H 0 0 N N N 15.249 9.773  78.164 -0.125 1.026  -0.012 H131 LAR 46 
LAR H141 1H14 H 0 0 N N N 15.573 6.984  76.929 -0.016 1.086  3.037  H141 LAR 47 
LAR H142 2H14 H 0 0 N N N 14.757 8.290  76.246 -1.416 0.609  2.047  H142 LAR 48 
LAR H151 1H15 H 0 0 N N N 17.277 7.985  75.536 -0.070 -1.340 2.932  H151 LAR 49 
LAR H161 1H16 H 0 0 N N N 18.584 7.564  77.262 2.147  -0.332 2.857  H161 LAR 50 
LAR H162 2H16 H 0 0 N N N 18.923 9.207  76.943 2.130  -1.751 1.778  H162 LAR 51 
LAR H181 1H18 H 0 0 N N N 18.547 7.307  79.834 4.075  0.574  1.558  H181 LAR 52 
LAR H191 1H19 H 0 0 N N N 18.897 8.119  81.898 3.153  1.523  -1.023 H191 LAR 53 
LAR H192 2H19 H 0 0 N N N 17.869 9.361  81.449 4.676  1.946  -0.169 H192 LAR 54 
LAR H211 1H21 H 0 0 N N N 14.628 14.648 75.130 -3.023 -4.337 -1.949 H211 LAR 55 
LAR H212 2H21 H 0 0 N N N 16.360 14.699 74.587 -4.520 -4.629 -1.030 H212 LAR 56 
LAR H213 3H21 H 0 0 N N N 15.224 13.855 73.608 -4.471 -3.352 -2.268 H213 LAR 57 
LAR H221 1H22 H 0 0 N N N 14.842 9.749  82.746 -2.048 5.509  -0.087 H221 LAR 58 
LAR H222 2H22 H 0 0 N N N 13.499 11.023 82.693 -3.404 4.542  -0.714 H222 LAR 59 
LAR H223 3H22 H 0 0 N N N 13.039 9.438  83.033 -2.575 4.048  0.782  H223 LAR 60 
# 
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 
LAR S1  C19  SING N N 1  
LAR S1  C20  SING N N 2  
LAR N1  C18  SING N N 3  
LAR N1  C20  SING N N 4  
LAR N1  HN1  SING N N 5  
LAR O1  C1   DOUB N N 6  
LAR O2  C1   SING N N 7  
LAR O2  C15  SING N N 8  
LAR O3  C13  SING N N 9  
LAR O3  C17  SING N N 10 
LAR O4  C17  SING N N 11 
LAR O4  HO4  SING N N 12 
LAR O5  C20  DOUB N N 13 
LAR C1  C2   SING N N 14 
LAR C2  C3   DOUB N Z 15 
LAR C2  H21  SING N N 16 
LAR C3  C4   SING N N 17 
LAR C3  C21  SING N N 18 
LAR C4  C5   SING N N 19 
LAR C4  H41  SING N N 20 
LAR C4  H42  SING N N 21 
LAR C5  C6   SING N N 22 
LAR C5  H51  SING N N 23 
LAR C5  H52  SING N N 24 
LAR C6  C7   DOUB N E 25 
LAR C6  H61  SING N N 26 
LAR C7  C8   SING N N 27 
LAR C7  H71  SING N N 28 
LAR C8  C9   DOUB N Z 29 
LAR C8  H81  SING N N 30 
LAR C9  C10  SING N N 31 
LAR C9  H91  SING N N 32 
LAR C10 C11  SING N N 33 
LAR C10 C22  SING N N 34 
LAR C10 H101 SING N N 35 
LAR C11 C12  SING N N 36 
LAR C11 H111 SING N N 37 
LAR C11 H112 SING N N 38 
LAR C12 C13  SING N N 39 
LAR C12 H121 SING N N 40 
LAR C12 H122 SING N N 41 
LAR C13 C14  SING N N 42 
LAR C13 H131 SING N N 43 
LAR C14 C15  SING N N 44 
LAR C14 H141 SING N N 45 
LAR C14 H142 SING N N 46 
LAR C15 C16  SING N N 47 
LAR C15 H151 SING N N 48 
LAR C16 C17  SING N N 49 
LAR C16 H161 SING N N 50 
LAR C16 H162 SING N N 51 
LAR C17 C18  SING N N 52 
LAR C18 C19  SING N N 53 
LAR C18 H181 SING N N 54 
LAR C19 H191 SING N N 55 
LAR C19 H192 SING N N 56 
LAR C21 H211 SING N N 57 
LAR C21 H212 SING N N 58 
LAR C21 H213 SING N N 59 
LAR C22 H221 SING N N 60 
LAR C22 H222 SING N N 61 
LAR C22 H223 SING N N 62 
# 
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 
LAR SMILES           ACDLabs              10.04 O=C3OC2CC(OC(O)(C1NC(=O)SC1)C2)CCC(C=CC=CCCC(=C3)C)C 
LAR InChI            InChI                1.02b 
InChI=1/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1/f/h23H 
LAR InChIKey         InChI                1.02b DDVBPZROPPMBLW-KQVRWLEFDV 
LAR SMILES_CANONICAL CACTVS               3.341 C[C@H]\1CC[C@@H]2C[C@H](C[C@@](O)(O2)[C@@H]3CSC(=O)N3)OC(=O)\C=C(C)/CC\C=C\C=C\1 
LAR SMILES           CACTVS               3.341 C[CH]1CC[CH]2C[CH](C[C](O)(O2)[CH]3CSC(=O)N3)OC(=O)C=C(C)CCC=CC=C1 
LAR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]\1CC[C@@H]2C[C@H](C[C@@](O2)([C@@H]3CSC(=O)N3)O)OC(=O)\C=C(/CC\C=C\C=C1)\C 
LAR SMILES           "OpenEye OEToolkits" 1.5.0 CC1CCC2CC(CC(O2)(C3CSC(=O)N3)O)OC(=O)C=C(CCC=CC=C1)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 
LAR "SYSTEMATIC NAME" ACDLabs              10.04 (4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-1,3-thiazolidin-2-one  
LAR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (4R)-4-[(1R,4S,5Z,7E,11Z,15R,17R)-17-hydroxy-4,11-dimethyl-13-oxo-14,18-dioxabicyclo[13.3.1]nonadeca-5,7,11-trien-17-yl]-1,3-thiazolidin-2-one 
# 
