data_XMO
# 
_chem_comp.id                                    XMO 
_chem_comp.name                                  "N-hydroxy-5'-O-(2-methylpropanoyl)cytidine" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C13 H19 N3 O7" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         Molnupiravir 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2023-08-30 
_chem_comp.pdbx_modified_date                    2024-03-08 
_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                        329.306 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     XMO 
_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        8TZ7 
_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.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 
XMO C10  C1  C 0 1 N N R N N N 152.568 149.454 138.047 0.811  -2.205 0.608  C10  XMO 1  
XMO C11  C2  C 0 1 N N R N N N 151.417 148.886 137.906 0.931  -1.314 -0.654 C11  XMO 2  
XMO C01  C3  C 0 1 N N N N N N 149.410 150.777 144.437 -5.514 1.275  -1.716 C01  XMO 3  
XMO C02  C4  C 0 1 N N N N N N 149.112 149.769 143.331 -4.805 1.986  -0.562 C02  XMO 4  
XMO C03  C5  C 0 1 N N N N N N 147.880 148.978 143.641 -5.840 2.692  0.316  C03  XMO 5  
XMO C04  C6  C 0 1 N N N N N N 150.322 148.844 143.055 -4.051 0.976  0.264  C04  XMO 6  
XMO C07  C7  C 0 1 N N N N N N 151.975 147.917 141.481 -2.403 -0.721 0.555  C07  XMO 7  
XMO C08  C8  C 0 1 N N R N N N 152.214 147.939 139.971 -1.345 -1.469 -0.259 C08  XMO 8  
XMO C09  C9  C 0 1 N N S N N N 152.996 149.219 139.567 -0.695 -2.565 0.609  C09  XMO 9  
XMO C14  C10 C 0 1 N N N N N N 149.643 150.412 138.801 3.130  -0.546 -1.404 C14  XMO 10 
XMO C15  C11 C 0 1 N N N N N N 148.585 151.437 138.578 4.186  0.295  -1.295 C15  XMO 11 
XMO C16  C12 C 0 1 N N N N N N 148.299 151.919 137.187 4.172  1.281  -0.287 C16  XMO 12 
XMO C18  C13 C 0 1 N N N N N N 150.109 150.361 136.293 2.098  0.537  0.408  C18  XMO 13 
XMO N13  N1  N 0 1 N N N N N N 150.398 149.881 137.672 2.082  -0.415 -0.543 N13  XMO 14 
XMO N17  N2  N 0 1 N N N N N N 149.046 151.391 136.066 3.132  1.368  0.531  N17  XMO 15 
XMO N20  N3  N 0 1 N N N N N N 147.276 152.908 136.973 5.232  2.149  -0.153 N20  XMO 16 
XMO O05  O1  O 0 1 N N N N N N 150.611 148.015 143.810 -4.316 0.834  1.435  O05  XMO 17 
XMO O06  O2  O 0 1 N N N N N N 151.098 149.026 141.810 -3.087 0.233  -0.300 O06  XMO 18 
XMO O12  O3  O 0 1 N N N N N N 151.076 148.052 139.326 -0.303 -0.563 -0.656 O12  XMO 19 
XMO O19  O4  O 0 1 N N N N N N 150.709 149.938 135.388 1.151  0.641  1.169  O19  XMO 20 
XMO O21  O5  O 0 1 N N N N N N 146.536 153.428 138.090 5.214  3.138  0.860  O21  XMO 21 
XMO O22  O6  O 0 1 N N N N N N 153.538 148.813 137.163 1.615  -3.380 0.482  O22  XMO 22 
XMO O23  O7  O 0 1 N N N N N N 154.298 149.019 139.657 -0.902 -3.853 0.026  O23  XMO 23 
XMO H101 H1  H 0 0 N N N N N N 152.539 150.537 137.858 1.078  -1.647 1.505  H101 XMO 24 
XMO H111 H2  H 0 0 N N N N N N 151.412 148.147 137.091 1.007  -1.928 -1.552 H111 XMO 25 
XMO H012 H3  H 0 0 N N N N N N 148.528 151.413 144.602 -6.059 2.006  -2.313 H012 XMO 26 
XMO H013 H4  H 0 0 N N N N N N 149.654 150.241 145.366 -4.776 0.772  -2.341 H013 XMO 27 
XMO H011 H5  H 0 0 N N N N N N 150.264 151.404 144.141 -6.212 0.540  -1.315 H011 XMO 28 
XMO H021 H6  H 0 0 N N N N N N 148.922 150.338 142.409 -4.106 2.721  -0.962 H021 XMO 29 
XMO H033 H7  H 0 0 N N N N N N 147.041 149.664 143.832 -6.538 1.957  0.716  H033 XMO 30 
XMO H031 H8  H 0 0 N N N N N N 147.636 148.329 142.787 -5.335 3.199  1.138  H031 XMO 31 
XMO H032 H9  H 0 0 N N N N N N 148.057 148.359 144.533 -6.385 3.423  -0.281 H032 XMO 32 
XMO H072 H10 H 0 0 N N N N N N 151.501 146.967 141.771 -3.125 -1.433 0.955  H072 XMO 33 
XMO H071 H11 H 0 0 N N N N N N 152.932 148.027 142.012 -1.921 -0.191 1.377  H071 XMO 34 
XMO H081 H12 H 0 0 N N N N N N 152.791 147.051 139.675 -1.805 -1.918 -1.139 H081 XMO 35 
XMO H091 H13 H 0 0 N N N N N N 152.647 150.069 140.172 -1.093 -2.537 1.623  H091 XMO 36 
XMO H141 H14 H 0 0 N N N N N N 149.851 150.061 139.801 3.117  -1.310 -2.167 H141 XMO 37 
XMO H151 H15 H 0 0 N N N N N N 148.027 151.831 139.414 5.026  0.212  -1.969 H151 XMO 38 
XMO H201 H16 H 0 0 N N N N N N 147.080 153.233 136.048 5.991  2.083  -0.753 H201 XMO 39 
XMO H211 H17 H 0 0 N N N N N N 145.904 154.066 137.782 6.001  3.699  0.875  H211 XMO 40 
XMO H221 H18 H 0 0 N N N N N N 154.385 149.230 137.266 1.505  -4.011 1.207  H221 XMO 41 
XMO H231 H19 H 0 0 N N N N N N 154.536 148.881 140.566 -0.465 -4.574 0.500  H231 XMO 42 
# 
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 
XMO O19 C18  DOUB N N 1  
XMO N17 C18  SING N N 2  
XMO N17 C16  DOUB N N 3  
XMO C18 N13  SING N N 4  
XMO N20 C16  SING N N 5  
XMO N20 O21  SING N N 6  
XMO O22 C10  SING N N 7  
XMO C16 C15  SING N N 8  
XMO N13 C11  SING N N 9  
XMO N13 C14  SING N N 10 
XMO C11 C10  SING N N 11 
XMO C11 O12  SING N N 12 
XMO C10 C09  SING N N 13 
XMO C15 C14  DOUB N N 14 
XMO O12 C08  SING N N 15 
XMO C09 O23  SING N N 16 
XMO C09 C08  SING N N 17 
XMO C08 C07  SING N N 18 
XMO C07 O06  SING N N 19 
XMO O06 C04  SING N N 20 
XMO C04 C02  SING N N 21 
XMO C04 O05  DOUB N N 22 
XMO C02 C03  SING N N 23 
XMO C02 C01  SING N N 24 
XMO C10 H101 SING N N 25 
XMO C11 H111 SING N N 26 
XMO C01 H012 SING N N 27 
XMO C01 H013 SING N N 28 
XMO C01 H011 SING N N 29 
XMO C02 H021 SING N N 30 
XMO C03 H033 SING N N 31 
XMO C03 H031 SING N N 32 
XMO C03 H032 SING N N 33 
XMO C07 H072 SING N N 34 
XMO C07 H071 SING N N 35 
XMO C08 H081 SING N N 36 
XMO C09 H091 SING N N 37 
XMO C14 H141 SING N N 38 
XMO C15 H151 SING N N 39 
XMO N20 H201 SING N N 40 
XMO O21 H211 SING N N 41 
XMO O22 H221 SING N N 42 
XMO O23 H231 SING N N 43 
# 
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 
XMO SMILES           ACDLabs              12.01 "CC(C)C(=O)OCC1OC(N2C=CC(=NC2=O)NO)C(O)C1O"                                                                                                                 
XMO InChI            InChI                1.06  "InChI=1S/C13H19N3O7/c1-6(2)12(19)22-5-7-9(17)10(18)11(23-7)16-4-3-8(15-21)14-13(16)20/h3-4,6-7,9-11,17-18,21H,5H2,1-2H3,(H,14,15,20)/t7-,9-,10-,11-/m1/s1" 
XMO InChIKey         InChI                1.06  HTNPEHXGEKVIHG-QCNRFFRDSA-N                                                                                                                                 
XMO SMILES_CANONICAL CACTVS               3.385 "CC(C)C(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=CC(=NC2=O)NO"                                                                                                
XMO SMILES           CACTVS               3.385 "CC(C)C(=O)OC[CH]1O[CH]([CH](O)[CH]1O)N2C=CC(=NC2=O)NO"                                                                                                     
XMO SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "CC(C)C(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)NO)O)O"                                                                                             
XMO SMILES           "OpenEye OEToolkits" 2.0.7 "CC(C)C(=O)OCC1C(C(C(O1)N2C=CC(=NC2=O)NO)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 
XMO "SYSTEMATIC NAME" ACDLabs              12.01 "N-hydroxy-5'-O-(2-methylpropanoyl)cytidine"                                                                                             
XMO "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.7 "[(2~{R},3~{S},4~{R},5~{R})-3,4-bis(oxidanyl)-5-[4-(oxidanylamino)-2-oxidanylidene-pyrimidin-1-yl]oxolan-2-yl]methyl 2-methylpropanoate" 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      XMO 
_pdbx_chem_comp_synonyms.name         Molnupiravir 
_pdbx_chem_comp_synonyms.provenance   PUBCHEM 
_pdbx_chem_comp_synonyms.type         ? 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
XMO "Create component"   2023-08-30 RCSB 
XMO "Other modification" 2023-08-30 RCSB 
XMO "Initial release"    2024-03-13 RCSB 
# 
