data_F5S
# 
_chem_comp.id                                    F5S 
_chem_comp.name                                  "(1aR,2Z,4E,6E,14R,15aR)-9,11-dihydroxy-6-{[(4-methoxyphenyl)methoxy]imino}-14-methyl-1a,6,7,14,15,15a-hexahydro-12H-oxireno[e][2]benzoxacyclotetradecin-12-one" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C26 H27 N O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2018-03-01 
_chem_comp.pdbx_modified_date                    2019-01-25 
_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                        465.495 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     F5S 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        6CJP 
_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 
F5S C10  C1  C 0 1 N N N 19.673 24.008 52.997 0.768  1.196  2.380  C10  F5S 1  
F5S C13  C2  C 0 1 N N N 22.017 26.134 54.043 3.645  1.995  0.067  C13  F5S 2  
F5S C15  C3  C 0 1 N N N 24.582 26.180 54.298 5.793  1.719  -0.957 C15  F5S 3  
F5S C17  C4  C 0 1 N N R 25.295 23.456 52.861 4.518  -0.538 -0.894 C17  F5S 4  
F5S C22  C5  C 0 1 N N N 16.741 24.939 55.836 -1.097 1.583  -1.300 C22  F5S 5  
F5S C24  C6  C 0 1 Y N N 16.377 27.422 55.997 -3.512 2.138  -0.948 C24  F5S 6  
F5S C26  C7  C 0 1 Y N N 15.378 28.650 54.184 -5.218 0.465  -1.133 C26  F5S 7  
F5S C28  C8  C 0 1 N N N 14.530 30.086 52.383 -6.840 -1.262 -1.338 C28  F5S 8  
F5S O01  O1  O 0 1 N N N 21.688 24.864 48.503 -0.798 -2.914 0.105  O01  F5S 9  
F5S C02  C9  C 0 1 Y N N 20.715 25.194 49.469 -1.056 -1.779 0.802  C02  F5S 10 
F5S C03  C10 C 0 1 Y N N 20.684 24.492 50.669 -0.010 -0.922 1.201  C03  F5S 11 
F5S C04  C11 C 0 1 N N N 21.743 23.400 50.842 1.370  -1.276 0.817  C04  F5S 12 
F5S O05  O2  O 0 1 N N N 22.414 23.278 52.084 1.614  -2.283 -0.025 O05  F5S 13 
F5S C06  C12 C 0 1 N N R 23.231 22.155 52.215 2.861  -2.431 -0.730 C06  F5S 14 
F5S C07  C13 C 0 1 N N N 23.237 21.665 53.651 3.970  -2.891 0.208  C07  F5S 15 
F5S O08  O3  O 0 1 N N N 22.005 22.669 49.902 2.299  -0.658 1.299  O08  F5S 16 
F5S C09  C14 C 0 1 Y N N 19.730 24.804 51.662 -0.314 0.235  1.923  C09  F5S 17 
F5S C11  C15 C 0 1 N N N 19.897 24.733 54.330 1.511  1.678  1.171  C11  F5S 18 
F5S C12  C16 C 0 1 N N N 21.270 25.255 54.773 2.915  2.056  1.184  C12  F5S 19 
F5S C14  C17 C 0 1 N N N 23.343 26.619 54.637 5.057  2.359  -0.032 C14  F5S 20 
F5S C16  C18 C 0 1 N N R 24.826 24.930 53.167 5.165  0.585  -1.730 C16  F5S 21 
F5S O18  O4  O 0 1 N N N 25.970 24.624 52.224 5.738  -0.715 -1.616 O18  F5S 22 
F5S C19  C19 C 0 1 N N N 24.620 22.580 51.821 3.228  -1.135 -1.444 C19  F5S 23 
F5S N20  N1  N 0 1 N N N 18.888 24.871 55.184 0.861  1.775  0.050  N20  F5S 24 
F5S O21  O5  O 0 1 N N N 17.634 24.404 54.870 -0.511 1.429  -0.006 O21  F5S 25 
F5S C23  C20 C 0 1 Y N N 16.254 26.254 55.253 -2.551 1.189  -1.243 C23  F5S 26 
F5S C25  C21 C 0 1 Y N N 15.940 28.623 55.456 -4.844 1.778  -0.890 C25  F5S 27 
F5S O27  O6  O 0 1 N N N 14.947 29.913 53.719 -6.528 0.108  -1.077 O27  F5S 28 
F5S C29  C22 C 0 1 Y N N 15.258 27.472 53.442 -4.252 -0.484 -1.434 C29  F5S 29 
F5S C30  C23 C 0 1 Y N N 15.700 26.272 53.976 -2.921 -0.121 -1.486 C30  F5S 30 
F5S C31  C24 C 0 1 Y N N 18.797 25.817 51.399 -1.620 0.536  2.238  C31  F5S 31 
F5S C32  C25 C 0 1 Y N N 18.835 26.518 50.183 -2.645 -0.303 1.838  C32  F5S 32 
F5S O33  O7  O 0 1 N N N 17.909 27.549 49.918 -3.930 0.006  2.150  O33  F5S 33 
F5S C34  C26 C 0 1 Y N N 19.794 26.208 49.220 -2.370 -1.455 1.124  C34  F5S 34 
F5S H102 H1  H 0 0 N N N 18.676 23.546 53.050 0.313  2.043  2.895  H102 F5S 35 
F5S H101 H2  H 0 0 N N N 20.438 23.221 52.931 1.453  0.684  3.057  H101 F5S 36 
F5S H131 H3  H 0 0 N N N 21.683 26.477 53.075 3.171  1.657  -0.862 H131 F5S 37 
F5S H151 H4  H 0 0 N N N 25.443 26.639 54.761 6.824  1.966  -1.126 H151 F5S 38 
F5S H171 H6  H 0 0 N N N 25.829 22.943 53.675 4.568  -0.382 0.190  H171 F5S 39 
F5S H222 H7  H 0 0 N N N 15.896 24.254 55.999 -1.015 2.624  -1.614 H222 F5S 40 
F5S H221 H8  H 0 0 N N N 17.263 25.111 56.789 -0.576 0.946  -2.013 H221 F5S 41 
F5S H241 H9  H 0 0 N N N 16.809 27.395 56.987 -3.221 3.161  -0.759 H241 F5S 42 
F5S H282 H10 H 0 0 N N N 14.236 31.134 52.223 -6.332 -1.895 -0.610 H282 F5S 43 
F5S H281 H11 H 0 0 N N N 15.357 29.830 51.705 -7.917 -1.411 -1.261 H281 F5S 44 
F5S H283 H12 H 0 0 N N N 13.672 29.429 52.179 -6.508 -1.525 -2.342 H283 F5S 45 
F5S H011 H13 H 0 0 N N N 22.069 24.019 48.712 -0.645 -3.691 0.661  H011 F5S 46 
F5S H061 H14 H 0 0 N N N 22.895 21.342 51.555 2.723  -3.212 -1.498 H061 F5S 47 
F5S H073 H15 H 0 0 N N N 22.221 21.355 53.937 3.700  -3.853 0.645  H073 F5S 48 
F5S H071 H16 H 0 0 N N N 23.921 20.809 53.743 4.900  -2.994 -0.351 H071 F5S 49 
F5S H072 H17 H 0 0 N N N 23.573 22.476 54.314 4.103  -2.156 1.002  H072 F5S 50 
F5S H121 H18 H 0 0 N N N 21.668 24.908 55.715 3.354  2.386  2.122  H121 F5S 51 
F5S H141 H19 H 0 0 N N N 23.287 27.383 55.398 5.493  3.103  0.603  H141 F5S 52 
F5S H2   H20 H 0 1 N N N 23.966 25.060 52.494 4.697  0.848  -2.671 H2   F5S 53 
F5S H192 H22 H 0 0 N N N 25.233 21.678 51.673 2.416  -0.411 -1.326 H192 F5S 54 
F5S H191 H23 H 0 0 N N N 24.559 23.142 50.877 3.352  -1.336 -2.513 H191 F5S 55 
F5S H251 H24 H 0 0 N N N 16.036 29.537 56.023 -5.595 2.519  -0.654 H251 F5S 56 
F5S H291 H25 H 0 0 N N N 14.822 27.497 52.454 -4.541 -1.508 -1.625 H291 F5S 57 
F5S H301 H26 H 0 0 N N N 15.615 25.358 53.406 -2.168 -0.859 -1.721 H301 F5S 58 
F5S H311 H27 H 0 0 N N N 18.045 26.059 52.136 -1.842 1.433  2.799  H311 F5S 59 
F5S H331 H28 H 0 0 N N N 17.322 27.646 50.659 -4.377 0.546  1.484  H331 F5S 60 
F5S H341 H29 H 0 0 N N N 19.822 26.751 48.287 -3.176 -2.104 0.813  H341 F5S 61 
# 
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 
F5S O01 C02  SING N N 1  
F5S C34 C02  DOUB Y N 2  
F5S C34 C32  SING Y N 3  
F5S C02 C03  SING Y N 4  
F5S O08 C04  DOUB N N 5  
F5S O33 C32  SING N N 6  
F5S C32 C31  DOUB Y N 7  
F5S C03 C04  SING N N 8  
F5S C03 C09  DOUB Y N 9  
F5S C04 O05  SING N N 10 
F5S C31 C09  SING Y N 11 
F5S C09 C10  SING N N 12 
F5S C19 C06  SING N N 13 
F5S C19 C17  SING N N 14 
F5S O05 C06  SING N N 15 
F5S C06 C07  SING N N 16 
F5S O18 C17  SING N N 17 
F5S O18 C16  SING N N 18 
F5S C28 O27  SING N N 19 
F5S C17 C16  SING N N 20 
F5S C10 C11  SING N N 21 
F5S C29 C30  DOUB Y N 22 
F5S C29 C26  SING Y N 23 
F5S O27 C26  SING N N 24 
F5S C30 C23  SING Y N 25 
F5S C13 C14  SING N N 26 
F5S C13 C12  DOUB N E 27 
F5S C26 C25  DOUB Y N 28 
F5S C15 C14  DOUB N Z 29 
F5S C11 C12  SING N N 30 
F5S C11 N20  DOUB N E 31 
F5S O21 N20  SING N N 32 
F5S O21 C22  SING N N 33 
F5S C23 C22  SING N N 34 
F5S C23 C24  DOUB Y N 35 
F5S C25 C24  SING Y N 36 
F5S C10 H102 SING N N 37 
F5S C10 H101 SING N N 38 
F5S C13 H131 SING N N 39 
F5S C15 H151 SING N N 40 
F5S C17 H171 SING N N 41 
F5S C22 H222 SING N N 42 
F5S C22 H221 SING N N 43 
F5S C24 H241 SING N N 44 
F5S C28 H282 SING N N 45 
F5S C28 H281 SING N N 46 
F5S C28 H283 SING N N 47 
F5S O01 H011 SING N N 48 
F5S C06 H061 SING N N 49 
F5S C07 H073 SING N N 50 
F5S C07 H071 SING N N 51 
F5S C07 H072 SING N N 52 
F5S C12 H121 SING N N 53 
F5S C14 H141 SING N N 54 
F5S C16 H2   SING N N 55 
F5S C19 H192 SING N N 56 
F5S C19 H191 SING N N 57 
F5S C25 H251 SING N N 58 
F5S C29 H291 SING N N 59 
F5S C30 H301 SING N N 60 
F5S C31 H311 SING N N 61 
F5S O33 H331 SING N N 62 
F5S C34 H341 SING N N 63 
F5S C16 C15  SING N N 64 
# 
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 
F5S SMILES           ACDLabs              12.01 "C2/C(C=CC=CC1C(O1)CC(OC(c3c(O)cc(cc23)O)=O)C)=N\OCc4ccc(OC)cc4" 
F5S InChI            InChI                1.03  
"InChI=1S/C26H27NO7/c1-16-11-24-23(34-24)6-4-3-5-19(27-32-15-17-7-9-21(31-2)10-8-17)12-18-13-20(28)14-22(29)25(18)26(30)33-16/h3-10,13-14,16,23-24,28-29H,11-12,15H2,1-2H3/b5-3+,6-4-,27-19-/t16-,23-,24-/m1/s1" 
F5S InChIKey         InChI                1.03  PACPIEIVCXUTPG-XVFAOPLPSA-N 
F5S SMILES_CANONICAL CACTVS               3.385 "COc1ccc(CO/N=C/2Cc3cc(O)cc(O)c3C(=O)O[C@H](C)C[C@H]4O[C@@H]4/C=C\C=C/2)cc1" 
F5S SMILES           CACTVS               3.385 "COc1ccc(CON=C2Cc3cc(O)cc(O)c3C(=O)O[CH](C)C[CH]4O[CH]4C=CC=C2)cc1" 
F5S SMILES_CANONICAL "OpenEye OEToolkits" 2.0.6 "C[C@@H]1C[C@@H]2C(O2)/C=C\C=C\C(=N\OCc3ccc(cc3)OC)\Cc4cc(cc(c4C(=O)O1)O)O" 
F5S SMILES           "OpenEye OEToolkits" 2.0.6 "CC1CC2C(O2)C=CC=CC(=NOCc3ccc(cc3)OC)Cc4cc(cc(c4C(=O)O1)O)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 
F5S "SYSTEMATIC NAME" ACDLabs              12.01 "(1aR,2Z,4E,6E,14R,15aR)-9,11-dihydroxy-6-{[(4-methoxyphenyl)methoxy]imino}-14-methyl-1a,6,7,14,15,15a-hexahydro-12H-oxireno[e][2]benzoxacyclotetradecin-12-one"             
F5S "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.6 "(4~{R},6~{R},9~{Z},11~{E},13~{E})-13-[(4-methoxyphenyl)methoxyimino]-4-methyl-17,19-bis(oxidanyl)-3,7-dioxatricyclo[13.4.0.0^{6,8}]nonadeca-1(15),9,11,16,18-pentaen-2-one" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
F5S "Create component"   2018-03-01 RCSB 
F5S "Other modification" 2018-03-01 RCSB 
F5S "Initial release"    2019-01-30 RCSB 
# 
