data_X8H # _chem_comp.id X8H _chem_comp.name "(1R,3S,4Z)-3-({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)-4-iminocyclopentane-1-carboxylic acid" _chem_comp.type non-polymer _chem_comp.pdbx_type HETAIN _chem_comp.formula "C14 H19 N2 O7 P" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2022-11-06 _chem_comp.pdbx_modified_date 2024-09-27 _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 358.284 _chem_comp.one_letter_code ? _chem_comp.three_letter_code X8H _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 8EZ1 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB _chem_comp.pdbx_pcm Y # 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.pdbx_backbone_atom_flag _chem_comp_atom.pdbx_n_terminal_atom_flag _chem_comp_atom.pdbx_c_terminal_atom_flag _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 X8H C01 C1 C 0 1 Y N N N N N 25.628 0.360 -19.295 -0.497 -3.612 0.140 C01 X8H 1 X8H C03 C2 C 0 1 Y N N N N N 25.864 2.230 -17.981 -2.161 -2.032 0.343 C03 X8H 2 X8H C04 C3 C 0 1 Y N N N N N 25.967 1.455 -16.838 -1.357 -1.051 -0.206 C04 X8H 3 X8H C05 C4 C 0 1 Y N N N N N 25.900 0.050 -16.895 -0.067 -1.374 -0.596 C05 X8H 4 X8H C06 C5 C 0 1 Y N N N N N 25.752 -0.489 -18.195 0.370 -2.683 -0.419 C06 X8H 5 X8H C07 C6 C 0 1 N N N N N N 25.426 -0.226 -20.731 -0.036 -5.032 0.344 C07 X8H 6 X8H C09 C7 C 0 1 N N N N N N 26.113 -0.855 -15.685 0.841 -0.332 -1.198 C09 X8H 7 X8H C10 C8 C 0 1 N N S N N N 25.261 -2.094 -15.259 1.631 0.360 -0.086 C10 X8H 8 X8H C11 C9 C 0 1 N N N N N N 24.724 -2.193 -13.927 2.587 -0.626 0.562 C11 X8H 9 X8H C12 C10 C 0 1 N N N N N N 23.753 -3.275 -13.794 3.832 0.194 0.885 C12 X8H 10 X8H C13 C11 C 0 1 N N R N N N 23.244 -3.559 -15.214 3.956 1.133 -0.341 C13 X8H 11 X8H C14 C12 C 0 1 N N N N N N 24.043 -2.568 -16.192 2.492 1.491 -0.678 C14 X8H 12 X8H C16 C13 C 0 1 N N N N N N 26.159 2.241 -15.492 -1.877 0.353 -0.378 C16 X8H 13 X8H C22 C14 C 0 1 N N N N N N 22.991 -5.016 -15.752 4.738 2.371 0.016 C22 X8H 14 X8H N02 N1 N 0 1 Y N N N N N 25.678 1.677 -19.178 -1.717 -3.264 0.498 N02 X8H 15 X8H N15 N2 N 0 1 N N N N N N 25.470 -1.924 -12.888 2.391 -1.869 0.789 N15 X8H 16 X8H O08 O1 O 0 1 N N N N N N 25.711 -1.868 -18.385 1.627 -3.046 -0.786 O08 X8H 17 X8H O17 O2 O 0 1 N N N N N N 27.573 2.104 -15.202 -3.222 0.424 0.097 O17 X8H 18 X8H O19 O3 O 0 1 N N N N N N 27.299 1.350 -12.790 -3.427 2.867 1.048 O19 X8H 19 X8H O20 O4 O 0 1 N N N N N N 29.627 2.241 -13.509 -4.124 2.313 -1.313 O20 X8H 20 X8H O21 O5 O 0 1 N N N N N N 27.463 3.643 -13.103 -5.594 1.463 0.554 O21 X8H 21 X8H O23 O6 O 0 1 N N N N N N 22.360 -5.833 -14.999 6.012 2.265 0.423 O23 X8H 22 X8H O24 O7 O 0 1 N N N N N N 23.421 -5.347 -16.919 4.217 3.458 -0.063 O24 X8H 23 X8H P18 P1 P 0 1 N N N N N N 28.010 2.355 -13.561 -4.093 1.778 0.066 P18 X8H 24 X8H H1 H1 H 0 1 N N N N N N 25.936 3.305 -17.900 -3.167 -1.786 0.649 H1 X8H 25 X8H H2 H2 H 0 1 N N N N N N 25.353 0.597 -21.457 -0.270 -5.621 -0.543 H2 X8H 26 X8H H3 H3 H 0 1 N N N N N N 26.282 -0.868 -20.989 1.041 -5.044 0.514 H3 X8H 27 X8H H4 H4 H 0 1 N N N N N N 24.501 -0.820 -20.757 -0.545 -5.458 1.208 H4 X8H 28 X8H H5 H5 H 0 1 N N N N N N 27.135 -1.245 -15.803 1.533 -0.811 -1.892 H5 X8H 29 X8H H6 H6 H 0 1 N Y N N N N 26.076 -0.178 -14.819 0.243 0.406 -1.733 H6 X8H 30 X8H H7 H7 H 0 1 N N N N N N 25.972 -2.930 -15.334 0.947 0.763 0.661 H7 X8H 31 X8H H8 H8 H 0 1 N N N N N N 22.921 -2.965 -13.144 3.689 0.770 1.799 H8 X8H 32 X8H H9 H9 H 0 1 N N N N N N 24.233 -4.171 -13.373 4.707 -0.451 0.970 H9 X8H 33 X8H H10 H10 H 0 1 N N N N N N 22.234 -3.124 -15.208 4.424 0.613 -1.177 H10 X8H 34 X8H H11 H11 H 0 1 N N N N N N 23.417 -1.716 -16.497 2.356 1.540 -1.758 H11 X8H 35 X8H H12 H12 H 0 1 N N N N N N 24.406 -3.095 -17.087 2.224 2.444 -0.221 H12 X8H 36 X8H H13 H13 H 0 1 N N N N N N 25.886 3.299 -15.615 -1.253 1.043 0.190 H13 X8H 37 X8H H14 H14 H 0 1 N N N N N N 25.551 1.797 -14.690 -1.850 0.623 -1.434 H14 X8H 38 X8H H15 H15 H 0 1 N N N N N N 25.263 -2.522 -12.114 3.084 -2.400 1.214 H15 X8H 39 X8H H16 H16 H 0 1 N N N N N N 25.808 -2.306 -17.548 1.694 -3.359 -1.699 H16 X8H 40 X8H H17 H17 H 0 1 N N N N N N 27.925 0.772 -12.369 -3.373 2.583 1.971 H17 X8H 41 X8H H18 H18 H 0 1 N N N N N N 28.175 4.216 -12.843 -6.176 2.235 0.561 H18 X8H 42 X8H H19 H19 H 0 1 N N N N N N 22.278 -6.671 -15.439 6.473 3.087 0.641 H19 X8H 43 # 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 X8H C07 C01 SING N N 1 X8H C01 N02 DOUB Y N 2 X8H C01 C06 SING Y N 3 X8H N02 C03 SING Y N 4 X8H O08 C06 SING N N 5 X8H C06 C05 DOUB Y N 6 X8H C03 C04 DOUB Y N 7 X8H O24 C22 DOUB N N 8 X8H C05 C04 SING Y N 9 X8H C05 C09 SING N N 10 X8H C04 C16 SING N N 11 X8H C14 C10 SING N N 12 X8H C14 C13 SING N N 13 X8H C22 C13 SING N N 14 X8H C22 O23 SING N N 15 X8H C09 C10 SING N N 16 X8H C16 O17 SING N N 17 X8H C10 C11 SING N N 18 X8H C13 C12 SING N N 19 X8H O17 P18 SING N N 20 X8H C11 C12 SING N N 21 X8H C11 N15 DOUB N N 22 X8H P18 O20 DOUB N N 23 X8H P18 O21 SING N N 24 X8H P18 O19 SING N N 25 X8H C03 H1 SING N N 26 X8H C07 H2 SING N N 27 X8H C07 H3 SING N N 28 X8H C07 H4 SING N N 29 X8H C09 H5 SING N N 30 X8H C09 H6 SING N N 31 X8H C10 H7 SING N N 32 X8H C12 H8 SING N N 33 X8H C12 H9 SING N N 34 X8H C13 H10 SING N N 35 X8H C14 H11 SING N N 36 X8H C14 H12 SING N N 37 X8H C16 H13 SING N N 38 X8H C16 H14 SING N N 39 X8H N15 H15 SING N N 40 X8H O08 H16 SING N N 41 X8H O19 H17 SING N N 42 X8H O21 H18 SING N N 43 X8H O23 H19 SING N N 44 # 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 X8H SMILES ACDLabs 12.01 "Oc1c(CC2CC(CC2=N)C(=O)O)c(cnc1C)COP(=O)(O)O" X8H InChI InChI 1.06 "InChI=1S/C14H19N2O7P/c1-7-13(17)11(10(5-16-7)6-23-24(20,21)22)3-8-2-9(14(18)19)4-12(8)15/h5,8-9,15,17H,2-4,6H2,1H3,(H,18,19)(H2,20,21,22)/b15-12-/t8-,9+/m0/s1" X8H InChIKey InChI 1.06 CTOWFYUCLIAQOJ-XPIHRMQRSA-N X8H SMILES_CANONICAL CACTVS 3.385 "Cc1ncc(CO[P](O)(O)=O)c(C[C@@H]2C[C@H](CC2=N)C(O)=O)c1O" X8H SMILES CACTVS 3.385 "Cc1ncc(CO[P](O)(O)=O)c(C[CH]2C[CH](CC2=N)C(O)=O)c1O" X8H SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "Cc1c(c(c(cn1)COP(=O)(O)O)C[C@@H]2C[C@H](CC2=N)C(=O)O)O" X8H SMILES "OpenEye OEToolkits" 2.0.7 "Cc1c(c(c(cn1)COP(=O)(O)O)CC2CC(CC2=N)C(=O)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 X8H "SYSTEMATIC NAME" ACDLabs 12.01 "(1R,3S,4Z)-3-({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)-4-iminocyclopentane-1-carboxylic acid" X8H "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "(1~{R},4~{S})-3-azanylidene-4-[[2-methyl-3-oxidanyl-5-(phosphonooxymethyl)pyridin-4-yl]methyl]cyclopentane-1-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 X8H "Create component" 2022-11-06 RCSB X8H "Initial release" 2023-02-22 RCSB X8H "Modify PCM" 2024-09-27 PDBE # _pdbx_chem_comp_pcm.pcm_id 1 _pdbx_chem_comp_pcm.comp_id X8H _pdbx_chem_comp_pcm.modified_residue_id LYS _pdbx_chem_comp_pcm.type None _pdbx_chem_comp_pcm.category "Covalent chemical modification" _pdbx_chem_comp_pcm.position "Amino-acid side chain" _pdbx_chem_comp_pcm.polypeptide_position "Any position" _pdbx_chem_comp_pcm.comp_id_linking_atom C09 _pdbx_chem_comp_pcm.modified_residue_id_linking_atom NZ _pdbx_chem_comp_pcm.uniprot_specific_ptm_accession ? _pdbx_chem_comp_pcm.uniprot_generic_ptm_accession ? #