data_DOL
# 
_chem_comp.id                                    DOL 
_chem_comp.name                                  5-(2-DIETHYLAMINO-ETHANESULFONYL)-21-HYDROXY-10-ISOPROPYL-11,19-DIMETHYL-9,26-DIOXA-3,15,28-TRIAZA-TRICYCLO[23.2.1.00,255]OCTACOSA-1(27),12,17,19,25(28)-PENTAENE-2,8,14,23-TETRAONE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C34 H50 N4 O9 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         DALFOPRISTIN 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2002-09-26 
_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                        690.847 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     DOL 
_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        1MRL 
_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 
DOL O7   O7   O 0 1 N N N 26.083 52.829 56.969 -1.684 -1.606 0.734  O7   DOL 1  
DOL C6   C6   C 0 1 N N N 26.563 54.094 56.641 -1.905 -0.412 0.804  C6   DOL 2  
DOL N5   N5   N 0 1 N N N 25.973 55.290 57.251 -1.074 0.322  1.539  N5   DOL 3  
DOL C4   C4   C 0 1 N N N 26.812 56.357 56.701 -1.276 1.678  2.115  C4   DOL 4  
DOL C3   C3   C 0 1 N N N 27.918 56.533 57.747 -0.668 1.546  3.535  C3   DOL 5  
DOL C2   C2   C 0 1 N N R 27.433 55.805 58.989 0.428  0.462  3.397  C2   DOL 6  
DOL S39  S39  S 0 1 N N N 27.772 56.812 60.414 0.112  -0.905 4.547  S39  DOL 7  
DOL O41  O41  O 0 1 N N N 27.144 58.429 60.101 1.172  -1.847 4.446  O41  DOL 8  
DOL O40  O40  O 0 1 N N N 27.021 56.111 61.845 -1.230 -1.340 4.389  O40  DOL 9  
DOL C42  C42  C 0 1 N N N 29.542 56.857 60.636 0.263  -0.012 6.118  C42  DOL 10 
DOL C43  C43  C 0 1 N N N 30.153 57.887 59.694 0.032  -0.981 7.280  C43  DOL 11 
DOL N44  N44  N 0 1 N N N 30.684 58.893 60.598 0.261  -0.284 8.552  N44  DOL 12 
DOL C47  C47  C 0 1 N N N 32.114 59.185 60.604 -0.882 0.615  8.753  C47  DOL 13 
DOL C48  C48  C 0 1 N N N 32.474 60.082 59.437 -0.707 1.377  10.068 C48  DOL 14 
DOL C45  C45  C 0 1 N N N 29.772 59.579 61.505 0.189  -1.301 9.610  C45  DOL 15 
DOL C46  C46  C 0 1 N N N 30.182 61.023 61.691 1.568  -1.934 9.803  C46  DOL 16 
DOL C1   C1   C 0 1 N N S 25.961 55.749 58.657 0.318  -0.027 1.933  C1   DOL 17 
DOL C8   C8   C 0 1 Y N N 27.685 54.413 55.689 -3.061 0.102  0.076  C8   DOL 18 
DOL C12  C12  C 0 1 Y N N 28.525 55.685 55.503 -4.025 0.960  0.474  C12  DOL 19 
DOL O11  O11  O 0 1 Y N N 29.114 55.576 54.192 -4.819 1.203  -0.575 O11  DOL 20 
DOL N9   N9   N 0 1 Y N N 27.692 53.657 54.493 -3.311 -0.186 -1.241 N9   DOL 21 
DOL C10  C10  C 0 1 Y N N 28.603 54.359 53.644 -4.337 0.510  -1.618 C10  DOL 22 
DOL C13  C13  C 0 1 N N N 28.839 53.738 52.294 -4.934 0.545  -3.012 C13  DOL 23 
DOL C14  C14  C 0 1 N N N 27.572 52.884 52.277 -3.876 0.141  -3.996 C14  DOL 24 
DOL O15  O15  O 0 1 N N N 27.457 51.828 53.236 -3.097 -0.727 -3.685 O15  DOL 25 
DOL C16  C16  C 0 1 N N N 26.385 53.145 51.355 -3.745 0.772  -5.351 C16  DOL 26 
DOL C17  C17  C 0 1 N N S 25.164 52.379 51.872 -2.994 -0.168 -6.299 C17  DOL 27 
DOL O18  O18  O 0 1 N N N 24.235 52.160 50.808 -3.069 -1.504 -5.799 O18  DOL 28 
DOL C19  C19  C 0 1 N N N 24.490 53.194 52.967 -1.553 0.248  -6.396 C19  DOL 29 
DOL C20  C20  C 0 1 N N N 23.540 52.404 53.863 -0.635 -0.586 -6.862 C20  DOL 30 
DOL C21  C21  C 0 1 N N N 23.289 50.917 53.641 -1.035 -1.952 -7.347 C21  DOL 31 
DOL C22  C22  C 0 1 N N N 22.577 53.237 54.694 0.780  -0.171 -6.919 C22  DOL 32 
DOL C23  C23  C 0 1 N N N 21.504 52.431 55.407 1.722  -1.087 -7.129 C23  DOL 33 
DOL C24  C24  C 0 1 N N N 20.683 53.448 56.180 3.179  -0.689 -7.148 C24  DOL 34 
DOL N25  N25  N 0 1 N N N 21.634 54.210 56.955 3.770  -1.101 -5.853 N25  DOL 35 
DOL C26  C26  C 0 1 N N N 21.259 54.860 58.186 3.817  -0.171 -4.868 C26  DOL 36 
DOL O27  O27  O 0 1 N N N 19.889 54.805 58.578 3.756  1.012  -5.139 O27  DOL 37 
DOL C28  C28  C 0 1 N N N 22.071 56.056 58.632 3.943  -0.607 -3.470 C28  DOL 38 
DOL C29  C29  C 0 1 N N N 21.875 56.253 60.124 4.088  0.309  -2.515 C29  DOL 39 
DOL C30  C30  C 0 1 N N R 22.701 57.460 60.531 4.173  -0.127 -1.075 C30  DOL 40 
DOL C31  C31  C 0 1 N N N 21.908 58.252 61.571 5.635  -0.113 -0.624 C31  DOL 41 
DOL C32  C32  C 0 1 N N R 24.169 57.168 60.926 3.361  0.827  -0.199 C32  DOL 42 
DOL C33  C33  C 0 1 N N N 24.470 57.618 62.363 2.623  1.825  -1.093 C33  DOL 43 
DOL C35  C35  C 0 1 N N N 24.988 59.052 62.450 1.239  1.272  -1.440 C35  DOL 44 
DOL C34  C34  C 0 1 N N N 23.289 57.402 63.306 2.469  3.156  -0.353 C34  DOL 45 
DOL O36  O36  O 0 1 N N N 24.580 55.786 60.875 2.397  0.086  0.593  O36  DOL 46 
DOL C37  C37  C 0 1 N N N 24.946 55.139 59.636 1.289  0.696  1.039  C37  DOL 47 
DOL O38  O38  O 0 1 N N N 24.304 53.898 59.320 1.068  1.840  0.720  O38  DOL 48 
DOL HC41 1HC4 H 0 0 N N N 27.184 56.162 55.668 -2.337 1.920  2.170  HC41 DOL 49 
DOL HC42 2HC4 H 0 0 N N N 26.260 57.293 56.454 -0.739 2.428  1.534  HC42 DOL 50 
DOL HC31 1HC3 H 0 0 N N N 28.921 56.196 57.396 -1.431 1.227  4.246  HC31 DOL 51 
DOL HC3A 2HC3 H 0 0 N N N 28.191 57.598 57.932 -0.229 2.493  3.849  HC3A DOL 52 
DOL HC2  HC2  H 0 1 N N N 27.889 54.814 59.220 1.412  0.892  3.581  HC2  DOL 53 
DOL H421 1H42 H 0 0 N N N 29.827 57.038 61.698 -0.479 0.784  6.156  H421 DOL 54 
DOL H422 2H42 H 0 0 N N N 30.005 55.850 60.514 1.262  0.417  6.198  H422 DOL 55 
DOL H431 1H43 H 0 0 N N N 30.896 57.472 58.973 0.722  -1.820 7.196  H431 DOL 56 
DOL H432 2H43 H 0 0 N N N 29.452 58.281 58.921 -0.993 -1.349 7.247  H432 DOL 57 
DOL H471 1H47 H 0 0 N N N 32.445 59.616 61.577 -1.801 0.031  8.791  H471 DOL 58 
DOL H472 2H47 H 0 0 N N N 32.728 58.254 60.617 -0.936 1.324  7.927  H472 DOL 59 
DOL H481 1H48 H 0 0 N N N 33.566 60.305 59.441 -1.556 2.045  10.217 H481 DOL 60 
DOL H482 2H48 H 0 0 N N N 32.142 59.650 58.463 -0.653 0.668  10.894 H482 DOL 61 
DOL H483 3H48 H 0 0 N N N 31.860 61.012 59.423 0.212  1.961  10.030 H483 DOL 62 
DOL H451 1H45 H 0 0 N N N 28.712 59.491 61.168 -0.130 -0.834 10.541 H451 DOL 63 
DOL H452 2H45 H 0 0 N N N 29.683 59.046 62.480 -0.527 -2.071 9.325  H452 DOL 64 
DOL H461 1H46 H 0 0 N N N 29.484 61.547 62.384 1.507  -2.713 10.563 H461 DOL 65 
DOL H462 2H46 H 0 0 N N N 31.241 61.110 62.027 1.903  -2.370 8.862  H462 DOL 66 
DOL H463 3H46 H 0 0 N N N 30.270 61.555 60.715 2.277  -1.170 10.123 H463 DOL 67 
DOL HC1  HC1  H 0 1 N N N 25.481 56.746 58.796 0.455  -1.102 1.870  HC1  DOL 68 
DOL HC12 HC12 H 0 0 N N N 28.678 56.531 56.192 -4.135 1.377  1.464  HC12 DOL 69 
DOL H131 1H13 H 0 0 N N N 29.002 54.429 51.434 -5.277 1.555  -3.238 H131 DOL 70 
DOL H132 2H13 H 0 0 N N N 29.810 53.215 52.133 -5.771 -0.150 -3.069 H132 DOL 71 
DOL H161 1H16 H 0 0 N N N 26.178 54.233 51.229 -3.196 1.709  -5.262 H161 DOL 72 
DOL H162 2H16 H 0 0 N N N 26.615 52.904 50.291 -4.738 0.973  -5.753 H162 DOL 73 
DOL HC17 HC17 H 0 0 N N N 25.493 51.393 52.277 -3.450 -0.125 -7.288 HC17 DOL 74 
DOL HO18 HO18 H 0 0 N N N 23.477 51.684 51.128 -3.998 -1.770 -5.850 HO18 DOL 75 
DOL HC19 HC19 H 0 0 N N N 24.675 54.273 53.100 -1.230 1.232  -6.085 HC19 DOL 76 
DOL H211 1H21 H 0 0 N N N 22.595 50.339 54.295 -0.184 -2.430 -7.832 H211 DOL 77 
DOL H212 2H21 H 0 0 N N N 22.959 50.778 52.584 -1.358 -2.558 -6.500 H212 DOL 78 
DOL H213 3H21 H 0 0 N N N 24.275 50.398 53.644 -1.854 -1.858 -8.060 H213 DOL 79 
DOL HC22 HC22 H 0 0 N N N 22.650 54.334 54.773 1.025  0.876  -6.825 HC22 DOL 80 
DOL HC23 HC23 H 0 0 N N N 21.353 51.339 55.371 1.461  -2.124 -7.291 HC23 DOL 81 
DOL H241 1H24 H 0 0 N N N 20.027 54.076 55.533 3.266  0.389  -7.269 H241 DOL 82 
DOL H242 2H24 H 0 0 N N N 19.869 52.993 56.792 3.690  -1.197 -7.967 H242 DOL 83 
DOL HN25 HN25 H 0 0 N N N 22.595 54.291 56.624 4.109  -1.999 -5.716 HN25 DOL 84 
DOL HC28 HC28 H 0 0 N N N 22.701 56.681 57.977 3.906  -1.660 -3.218 HC28 DOL 85 
DOL HC29 HC29 H 0 0 N N N 21.248 55.634 60.788 4.168  1.362  -2.754 HC29 DOL 86 
DOL HC30 HC30 H 0 0 N N N 22.856 58.091 59.625 3.774  -1.137 -0.978 HC30 DOL 87 
DOL H311 1H31 H 0 0 N N N 22.514 59.138 61.869 6.215  -0.794 -1.248 H311 DOL 88 
DOL H312 2H31 H 0 0 N N N 20.888 58.528 61.214 6.035  0.896  -0.720 H312 DOL 89 
DOL H313 3H31 H 0 0 N N N 21.599 57.628 62.442 5.698  -0.432 0.415  H313 DOL 90 
DOL HC32 HC32 H 0 0 N N N 24.730 57.740 60.150 4.035  1.368  0.465  HC32 DOL 91 
DOL HC33 HC33 H 0 0 N N N 25.298 56.955 62.706 3.192  1.982  -2.009 HC33 DOL 92 
DOL H351 1H35 H 0 0 N N N 25.206 59.378 63.493 0.519  2.090  -1.474 H351 DOL 93 
DOL H352 2H35 H 0 0 N N N 25.880 59.191 61.796 1.278  0.780  -2.412 H352 DOL 94 
DOL H353 3H35 H 0 0 N N N 24.283 59.758 61.952 0.935  0.552  -0.680 H353 DOL 95 
DOL H341 1H34 H 0 0 N N N 23.507 57.728 64.349 2.557  2.987  0.719  H341 DOL 96 
DOL H342 2H34 H 0 0 N N N 22.369 57.897 62.915 3.250  3.844  -0.678 H342 DOL 97 
DOL H343 3H34 H 0 0 N N N 22.946 56.341 63.282 1.492  3.584  -0.576 H343 DOL 98 
# 
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 
DOL O7  C6   DOUB N N 1   
DOL C6  N5   SING N N 2   
DOL C6  C8   SING N N 3   
DOL N5  C4   SING N N 4   
DOL N5  C1   SING N N 5   
DOL C4  C3   SING N N 6   
DOL C4  HC41 SING N N 7   
DOL C4  HC42 SING N N 8   
DOL C3  C2   SING N N 9   
DOL C3  HC31 SING N N 10  
DOL C3  HC3A SING N N 11  
DOL C2  S39  SING N N 12  
DOL C2  C1   SING N N 13  
DOL C2  HC2  SING N N 14  
DOL S39 O41  DOUB N N 15  
DOL S39 O40  DOUB N N 16  
DOL S39 C42  SING N N 17  
DOL C42 C43  SING N N 18  
DOL C42 H421 SING N N 19  
DOL C42 H422 SING N N 20  
DOL C43 N44  SING N N 21  
DOL C43 H431 SING N N 22  
DOL C43 H432 SING N N 23  
DOL N44 C47  SING N N 24  
DOL N44 C45  SING N N 25  
DOL C47 C48  SING N N 26  
DOL C47 H471 SING N N 27  
DOL C47 H472 SING N N 28  
DOL C48 H481 SING N N 29  
DOL C48 H482 SING N N 30  
DOL C48 H483 SING N N 31  
DOL C45 C46  SING N N 32  
DOL C45 H451 SING N N 33  
DOL C45 H452 SING N N 34  
DOL C46 H461 SING N N 35  
DOL C46 H462 SING N N 36  
DOL C46 H463 SING N N 37  
DOL C1  C37  SING N N 38  
DOL C1  HC1  SING N N 39  
DOL C8  C12  DOUB Y N 40  
DOL C8  N9   SING Y N 41  
DOL C12 O11  SING Y N 42  
DOL C12 HC12 SING N N 43  
DOL O11 C10  SING Y N 44  
DOL N9  C10  DOUB Y N 45  
DOL C10 C13  SING N N 46  
DOL C13 C14  SING N N 47  
DOL C13 H131 SING N N 48  
DOL C13 H132 SING N N 49  
DOL C14 O15  DOUB N N 50  
DOL C14 C16  SING N N 51  
DOL C16 C17  SING N N 52  
DOL C16 H161 SING N N 53  
DOL C16 H162 SING N N 54  
DOL C17 O18  SING N N 55  
DOL C17 C19  SING N N 56  
DOL C17 HC17 SING N N 57  
DOL O18 HO18 SING N N 58  
DOL C19 C20  DOUB N E 59  
DOL C19 HC19 SING N N 60  
DOL C20 C21  SING N N 61  
DOL C20 C22  SING N N 62  
DOL C21 H211 SING N N 63  
DOL C21 H212 SING N N 64  
DOL C21 H213 SING N N 65  
DOL C22 C23  DOUB N E 66  
DOL C22 HC22 SING N N 67  
DOL C23 C24  SING N N 68  
DOL C23 HC23 SING N N 69  
DOL C24 N25  SING N N 70  
DOL C24 H241 SING N N 71  
DOL C24 H242 SING N N 72  
DOL N25 C26  SING N N 73  
DOL N25 HN25 SING N N 74  
DOL C26 O27  DOUB N N 75  
DOL C26 C28  SING N N 76  
DOL C28 C29  DOUB N E 77  
DOL C28 HC28 SING N N 78  
DOL C29 C30  SING N N 79  
DOL C29 HC29 SING N N 80  
DOL C30 C31  SING N N 81  
DOL C30 C32  SING N N 82  
DOL C30 HC30 SING N N 83  
DOL C31 H311 SING N N 84  
DOL C31 H312 SING N N 85  
DOL C31 H313 SING N N 86  
DOL C32 C33  SING N N 87  
DOL C32 O36  SING N N 88  
DOL C32 HC32 SING N N 89  
DOL C33 C35  SING N N 90  
DOL C33 C34  SING N N 91  
DOL C33 HC33 SING N N 92  
DOL C35 H351 SING N N 93  
DOL C35 H352 SING N N 94  
DOL C35 H353 SING N N 95  
DOL C34 H341 SING N N 96  
DOL C34 H342 SING N N 97  
DOL C34 H343 SING N N 98  
DOL O36 C37  SING N N 99  
DOL C37 O38  DOUB N N 100 
# 
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 
DOL SMILES           ACDLabs              10.04 O=S(=O)(CCN(CC)CC)C3CCN2C(=O)c1nc(oc1)CC(=O)CC(O)C=C(C=CCNC(=O)C=CC(C)C(OC(=O)C23)C(C)C)C 
DOL InChI            InChI                1.02b 
;InChI=1/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9+,12-11+,23-18+/t24-,25-,28-,31-,32-/m1/s1/f/h35H
;
DOL InChIKey         InChI                1.02b SUYRLXYYZQTJHF-JTLHYENQDL 
DOL SMILES_CANONICAL CACTVS               3.341 CCN(CC)CC[S](=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC/C=C/C(=C/[C@@H](O)CC(=O)Cc3occ(n3)C2=O)C 
DOL SMILES           CACTVS               3.341 CCN(CC)CC[S](=O)(=O)[CH]1CCN2[CH]1C(=O)O[CH](C(C)C)[CH](C)C=CC(=O)NCC=CC(=C[CH](O)CC(=O)Cc3occ(n3)C2=O)C 
DOL SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCN(CC)CCS(=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@@H]([C@@H](\C=C\C(=O)NC/C=C/C(=C/[C@H](CC(=O)Cc3nc(co3)C2=O)O)/C)C)C(C)C 
DOL SMILES           "OpenEye OEToolkits" 1.5.0 CCN(CC)CCS(=O)(=O)C1CCN2C1C(=O)OC(C(C=CC(=O)NCC=CC(=CC(CC(=O)Cc3nc(co3)C2=O)O)C)C)C(C)C 
# 
_pdbx_chem_comp_identifier.comp_id           DOL 
_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        
(3R,4R,5E,10E,12E,14S,26R,26aS)-26-{[2-(diethylamino)ethyl]sulfonyl}-14-hydroxy-4,12-dimethyl-3-(1-methylethyl)-8,9,14,15,24,25,26,26a-octahydro-1H,3H,22H-21,18-(azeno)pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone 
# 
