data_USL
# 
_chem_comp.id                                    USL 
_chem_comp.name                                  "3-carboxy-1-cyclopropyl-6-fluoro-7-(4-beta-D-glucopyranuronosyl-3,4-dihydropyrazin-1(2H)-yl)-4-oxo-1,4-dihydroquinoline" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H24 F N3 O9" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-08-24 
_chem_comp.pdbx_modified_date                    2023-06-16 
_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                        505.450 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     USL 
_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        8E72 
_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 
USL C02 C1  C 0 1 N N N 16.788 18.840 3.985  7.909  -0.373 -0.299 C02 USL 1  
USL C04 C2  C 0 1 N N N 16.959 18.745 5.519  6.456  -0.183 -0.187 C04 USL 2  
USL C05 C3  C 0 1 N N N 18.074 18.295 6.142  5.904  1.078  -0.292 C05 USL 3  
USL C07 C4  C 0 1 N N N 19.434 17.723 8.222  4.082  2.659  -0.317 C07 USL 4  
USL C08 C5  C 0 1 N N N 20.715 18.409 8.836  4.471  3.445  -1.571 C08 USL 5  
USL C09 C6  C 0 1 N N N 20.771 17.633 7.541  5.101  3.797  -0.222 C09 USL 6  
USL C10 C7  C 0 1 Y N N 17.125 18.591 8.368  3.679  0.270  0.017  C10 USL 7  
USL C11 C8  C 0 1 Y N N 17.227 18.511 9.763  2.320  0.543  0.110  C11 USL 8  
USL C12 C9  C 0 1 Y N N 16.229 18.843 10.652 1.422  -0.493 0.318  C12 USL 9  
USL C14 C10 C 0 1 N N N 16.129 19.873 12.868 -0.552 0.080  1.715  C14 USL 10 
USL C15 C11 C 0 1 N N N 17.275 20.745 13.344 -1.874 -0.699 1.800  C15 USL 11 
USL C17 C12 C 0 1 N N R 19.193 20.951 14.711 -4.111 -0.052 0.763  C17 USL 12 
USL C19 C13 C 0 1 N N S 20.960 22.115 13.350 -6.272 -0.711 -0.041 C19 USL 13 
USL C20 C14 C 0 1 N N N 21.031 22.410 11.815 -6.954 -1.667 -0.986 C20 USL 14 
USL C23 C15 C 0 1 N N S 21.917 20.993 13.707 -6.619 0.728  -0.430 C23 USL 15 
USL C25 C16 C 0 1 N N S 21.682 20.826 15.244 -5.875 1.693  0.497  C25 USL 16 
USL C27 C17 C 0 1 N N R 20.318 20.141 15.455 -4.372 1.414  0.406  C27 USL 17 
USL C29 C18 C 0 1 N N N 18.910 19.088 13.267 -2.063 -0.283 -0.633 C29 USL 18 
USL C30 C19 C 0 1 N N N 18.024 18.328 12.232 -0.746 -0.220 -0.735 C30 USL 19 
USL C31 C20 C 0 1 Y N N 15.033 19.319 10.059 1.873  -1.811 0.434  C31 USL 20 
USL C33 C21 C 0 1 Y N N 14.855 19.431 8.670  3.205  -2.094 0.344  C33 USL 21 
USL C34 C22 C 0 1 Y N N 15.914 19.062 7.801  4.123  -1.061 0.135  C34 USL 22 
USL C35 C23 C 0 1 N N N 15.787 19.156 6.296  5.565  -1.334 0.033  C35 USL 23 
USL F32 F1  F 0 1 N N N 13.999 19.675 10.852 0.985  -2.810 0.636  F32 USL 24 
USL N06 N1  N 0 1 N N N 18.227 18.203 7.561  4.584  1.289  -0.194 N06 USL 25 
USL N13 N2  N 0 1 N N N 16.537 18.694 12.067 0.061  -0.218 0.412  N13 USL 26 
USL N16 N3  N 0 1 N N N 18.207 19.982 14.176 -2.681 -0.342 0.624  N16 USL 27 
USL O01 O1  O 0 1 N N N 17.784 18.608 3.256  8.634  0.584  -0.486 O01 USL 28 
USL O03 O2  O 0 1 N N N 15.634 19.123 3.607  8.437  -1.608 -0.190 O03 USL 29 
USL O18 O3  O 0 1 N N N 19.641 21.697 13.581 -4.857 -0.895 -0.117 O18 USL 30 
USL O21 O4  O 0 1 N N N 21.600 23.463 11.501 -8.294 -1.744 -1.011 O21 USL 31 
USL O22 O5  O 0 1 N N N 20.488 21.589 11.063 -6.295 -2.363 -1.721 O22 USL 32 
USL O24 O6  O 0 1 N N N 23.239 21.427 13.486 -8.028 0.931  -0.300 O24 USL 33 
USL O26 O7  O 0 1 N N N 22.658 19.993 15.807 -6.136 3.039  0.094  O26 USL 34 
USL O28 O8  O 0 1 N N N 20.022 20.205 16.826 -3.672 2.260  1.321  O28 USL 35 
USL O36 O9  O 0 1 N N N 14.773 19.554 5.758  6.005  -2.467 0.127  O36 USL 36 
USL H1  H1  H 0 1 N N N 18.904 17.984 5.525  6.557  1.922  -0.458 H1  USL 37 
USL H2  H2  H 0 1 N N N 19.230 16.792 8.771  3.091  2.836  0.100  H2  USL 38 
USL H3  H3  H 0 1 N N N 21.179 18.003 9.747  5.101  2.941  -2.305 H3  USL 39 
USL H4  H4  H 0 1 N N N 20.814 19.505 8.831  3.735  4.137  -1.979 H4  USL 40 
USL H5  H5  H 0 1 N N N 21.299 16.668 7.511  4.780  4.721  0.257  H5  USL 41 
USL H6  H6  H 0 1 N N N 20.934 18.170 6.595  6.146  3.525  -0.068 H6  USL 42 
USL H7  H7  H 0 1 N N N 18.163 18.161 10.174 1.964  1.558  0.022  H7  USL 43 
USL H8  H8  H 0 1 N N N 15.461 20.492 12.251 -0.747 1.149  1.796  H8  USL 44 
USL H9  H9  H 0 1 N N N 15.582 19.514 13.752 0.115  -0.236 2.518  H9  USL 45 
USL H10 H10 H 0 1 N N N 17.814 21.139 12.470 -1.673 -1.770 1.798  H10 USL 46 
USL H11 H11 H 0 1 N N N 16.870 21.581 13.933 -2.407 -0.424 2.711  H11 USL 47 
USL H12 H12 H 0 1 N N N 18.702 21.614 15.439 -4.420 -0.236 1.792  H12 USL 48 
USL H13 H13 H 0 1 N N N 21.210 23.025 13.915 -6.609 -0.904 0.977  H13 USL 49 
USL H14 H14 H 0 1 N N N 21.669 20.065 13.170 -6.318 0.909  -1.462 H14 USL 50 
USL H15 H15 H 0 1 N N N 21.673 21.818 15.719 -6.212 1.546  1.523  H15 USL 51 
USL H16 H16 H 0 1 N N N 20.347 19.108 15.079 -4.025 1.608  -0.609 H16 USL 52 
USL H17 H17 H 0 1 N N N 19.981 18.959 13.307 -2.669 -0.289 -1.527 H17 USL 53 
USL H18 H18 H 0 1 N N N 18.455 17.542 11.629 -0.287 -0.170 -1.711 H18 USL 54 
USL H19 H19 H 0 1 N N N 13.921 19.794 8.268  3.550  -3.114 0.434  H19 USL 55 
USL H20 H20 H 0 1 N N N 15.607 19.141 2.658  9.398  -1.683 -0.271 H20 USL 56 
USL H21 H21 H 0 1 N N N 21.568 23.572 10.558 -8.686 -2.371 -1.634 H21 USL 57 
USL H22 H22 H 0 1 N N N 23.843 20.728 13.708 -8.562 0.348  -0.856 H22 USL 58 
USL H23 H23 H 0 1 N N N 22.499 19.904 16.739 -7.071 3.283  0.120  H23 USL 59 
USL H24 H24 H 0 1 N N N 20.680 19.726 17.315 -3.793 3.205  1.154  H24 USL 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 
USL O01 C02 DOUB N N 1  
USL O03 C02 SING N N 2  
USL C02 C04 SING N N 3  
USL C04 C05 DOUB N N 4  
USL C04 C35 SING N N 5  
USL O36 C35 DOUB N N 6  
USL C05 N06 SING N N 7  
USL C35 C34 SING N N 8  
USL C09 C07 SING N N 9  
USL C09 C08 SING N N 10 
USL N06 C07 SING N N 11 
USL N06 C10 SING N N 12 
USL C34 C10 DOUB Y N 13 
USL C34 C33 SING Y N 14 
USL C07 C08 SING N N 15 
USL C10 C11 SING Y N 16 
USL C33 C31 DOUB Y N 17 
USL C11 C12 DOUB Y N 18 
USL C31 C12 SING Y N 19 
USL C31 F32 SING N N 20 
USL C12 N13 SING N N 21 
USL O22 C20 DOUB N N 22 
USL O21 C20 SING N N 23 
USL C20 C19 SING N N 24 
USL N13 C30 SING N N 25 
USL N13 C14 SING N N 26 
USL C30 C29 DOUB N N 27 
USL C14 C15 SING N N 28 
USL C29 N16 SING N N 29 
USL C15 N16 SING N N 30 
USL C19 O18 SING N N 31 
USL C19 C23 SING N N 32 
USL O24 C23 SING N N 33 
USL O18 C17 SING N N 34 
USL C23 C25 SING N N 35 
USL N16 C17 SING N N 36 
USL C17 C27 SING N N 37 
USL C25 C27 SING N N 38 
USL C25 O26 SING N N 39 
USL C27 O28 SING N N 40 
USL C05 H1  SING N N 41 
USL C07 H2  SING N N 42 
USL C08 H3  SING N N 43 
USL C08 H4  SING N N 44 
USL C09 H5  SING N N 45 
USL C09 H6  SING N N 46 
USL C11 H7  SING N N 47 
USL C14 H8  SING N N 48 
USL C14 H9  SING N N 49 
USL C15 H10 SING N N 50 
USL C15 H11 SING N N 51 
USL C17 H12 SING N N 52 
USL C19 H13 SING N N 53 
USL C23 H14 SING N N 54 
USL C25 H15 SING N N 55 
USL C27 H16 SING N N 56 
USL C29 H17 SING N N 57 
USL C30 H18 SING N N 58 
USL C33 H19 SING N N 59 
USL O03 H20 SING N N 60 
USL O21 H21 SING N N 61 
USL O24 H22 SING N N 62 
USL O26 H23 SING N N 63 
USL O28 H24 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 
USL SMILES           ACDLabs              12.01 "O=C(O)C1=CN(C2CC2)c2cc(c(F)cc2C1=O)N1CCN(C=C1)C1OC(C(O)C(O)C1O)C(=O)O"                                                                                                                                                  
USL InChI            InChI                1.06  "InChI=1S/C23H24FN3O9/c24-13-7-11-14(27(10-1-2-10)9-12(16(11)28)22(32)33)8-15(13)25-3-5-26(6-4-25)21-19(31)17(29)18(30)20(36-21)23(34)35/h3,5,7-10,17-21,29-31H,1-2,4,6H2,(H,32,33)(H,34,35)/t17-,18-,19+,20-,21+/m0/s1" 
USL InChIKey         InChI                1.06  CWGBMWFHBQHVMG-JRSUCEMESA-N                                                                                                                                                                                              
USL SMILES_CANONICAL CACTVS               3.385 "O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C(O)=O)N2CCN(C=C2)c3cc4N(C=C(C(O)=O)C(=O)c4cc3F)C5CC5"                                                                                                                          
USL SMILES           CACTVS               3.385 "O[CH]1[CH](O)[CH](O[CH]([CH]1O)C(O)=O)N2CCN(C=C2)c3cc4N(C=C(C(O)=O)C(=O)c4cc3F)C5CC5"                                                                                                                                   
USL SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "c1c2c(cc(c1F)N3CCN(C=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)N(C=C(C2=O)C(=O)O)C5CC5"                                                                                                                        
USL SMILES           "OpenEye OEToolkits" 2.0.7 "c1c2c(cc(c1F)N3CCN(C=C3)C4C(C(C(C(O4)C(=O)O)O)O)O)N(C=C(C2=O)C(=O)O)C5CC5"                                                                                                                                              
# 
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 
USL "SYSTEMATIC NAME" ACDLabs              12.01 "3-carboxy-1-cyclopropyl-6-fluoro-7-(4-beta-D-glucopyranuronosyl-3,4-dihydropyrazin-1(2H)-yl)-4-oxo-1,4-dihydroquinoline"                                                       
USL "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "7-[4-[(2~{R},3~{R},4~{S},5~{S},6~{S})-6-carboxy-3,4,5-tris(oxidanyl)oxan-2-yl]-2,3-dihydropyrazin-1-yl]-1-cyclopropyl-6-fluoranyl-4-oxidanylidene-quinoline-3-carboxylic acid" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
USL "Create component" 2022-08-24 RCSB 
USL "Initial release"  2023-06-21 RCSB 
# 
