data_OTO
# 
_chem_comp.id                                    OTO 
_chem_comp.name                                  "1-cyclopropylcarbonylpyrazolo[4,3-c]pyridine-3-carbonitrile" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C11 H8 N4 O" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2022-09-20 
_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                        212.207 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     OTO 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        8B1Y 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
_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 
OTO C4  C1  C 0 1 N N N N N N 10.143 5.267 0.865  -2.918 0.701  -0.076 C4  OTO 1  
OTO C5  C2  C 0 1 N N N N N N 11.105 4.128 0.977  -4.268 0.291  -0.668 C5  OTO 2  
OTO C6  C3  C 0 1 N N N N N N 11.194 5.053 -0.137 -4.122 0.481  0.843  C6  OTO 3  
OTO C3  C4  C 0 1 N N N N N N 8.787  4.857 0.507  -1.825 -0.336 -0.052 C3  OTO 4  
OTO O1  O1  O 0 1 N N N N N N 8.439  4.160 -0.403 -2.107 -1.511 -0.049 O1  OTO 5  
OTO N2  N2  N 0 1 Y Y N N N N 7.866  5.309 1.465  -0.533 0.047  -0.033 N2  OTO 6  
OTO H1  H1  H 0 1 N N N N N N 10.263 6.103 1.569  -2.589 1.728  -0.236 H1  OTO 7  
OTO H2  H2  H 0 1 N N N N N N 10.760 3.097 0.810  -4.826 1.048  -1.219 H2  OTO 8  
OTO H3  H3  H 0 1 N N N N N N 11.877 4.134 1.761  -4.365 -0.729 -1.041 H3  OTO 9  
OTO H4  H4  H 0 1 N N N N N N 10.923 4.716 -1.148 -4.123 -0.414 1.465  H4  OTO 10 
OTO H5  H5  H 0 1 N N N N N N 12.040 5.753 -0.198 -4.584 1.363  1.286  H5  OTO 11 
OTO N1  N1  N 0 1 Y Y N N N N ?      ?     ?      -0.080 1.372  -0.034 N1  OTO 12 
OTO C1  C5  C 0 1 Y Y N N N N ?      ?     ?      1.232  1.397  -0.014 C1  OTO 13 
OTO C8  C8  C 0 1 Y Y N N N N ?      ?     ?      1.703  0.006  0.002  C8  OTO 14 
OTO C9  C9  C 0 1 Y Y N N N N ?      ?     ?      0.548  -0.800 -0.005 C9  OTO 15 
OTO C10 C10 C 0 1 Y Y N N N N ?      ?     ?      0.710  -2.183 0.007  C10 OTO 16 
OTO C11 C11 C 0 1 Y Y N N N N ?      ?     ?      1.976  -2.701 0.026  C11 OTO 17 
OTO N3  N3  N 0 1 Y Y N N N N ?      ?     ?      3.044  -1.920 0.033  N3  OTO 18 
OTO C13 C13 C 0 1 Y Y N N N N ?      ?     ?      2.954  -0.607 0.026  C13 OTO 19 
OTO C2  C6  C 0 1 N Y N N N N ?      ?     ?      2.055  2.569  -0.008 C2  OTO 20 
OTO N4  N4  N 0 1 N Y N N N N ?      ?     ?      2.708  3.499  -0.003 N4  OTO 21 
OTO H6  H6  H 0 1 N Y N N N N ?      ?     ?      -0.150 -2.837 0.002  H6  OTO 22 
OTO H7  H7  H 0 1 N Y N N N N ?      ?     ?      2.107  -3.773 0.035  H7  OTO 23 
OTO H8  H8  H 0 1 N Y N N N N ?      ?     ?      3.850  -0.004 0.032  H8  OTO 24 
# 
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 
OTO O1  C3  DOUB N N 1  
OTO C6  C4  SING N N 2  
OTO C6  C5  SING N N 3  
OTO C3  C4  SING N N 4  
OTO C4  C5  SING N N 5  
OTO C3  N2  SING N N 6  
OTO C4  H1  SING N N 7  
OTO C5  H2  SING N N 8  
OTO C5  H3  SING N N 9  
OTO C6  H4  SING N N 10 
OTO C6  H5  SING N N 11 
OTO N2  N1  SING Y N 12 
OTO N1  C1  DOUB Y N 13 
OTO C1  C8  SING Y N 14 
OTO C8  C9  DOUB Y N 15 
OTO C9  N2  SING Y N 16 
OTO C9  C10 SING Y N 17 
OTO C10 C11 DOUB Y N 18 
OTO C11 N3  SING Y N 19 
OTO N3  C13 DOUB Y N 20 
OTO C13 C8  SING Y N 21 
OTO C1  C2  SING N N 22 
OTO C2  N4  TRIP N N 23 
OTO C10 H6  SING N N 24 
OTO C11 H7  SING N N 25 
OTO C13 H8  SING N N 26 
# 
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 
OTO InChI            InChI                1.06    "InChI=1S/C11H8N4O/c12-5-9-8-6-13-4-3-10(8)15(14-9)11(16)7-1-2-7/h3-4,6-7H,1-2H2" 
OTO InChIKey         InChI                1.06    DHYXAKZNFKQCOW-UHFFFAOYSA-N                                                       
OTO SMILES_CANONICAL CACTVS               3.385   "O=C(C1CC1)n2nc(C#N)c3cnccc23"                                                    
OTO SMILES           CACTVS               3.385   "O=C(C1CC1)n2nc(C#N)c3cnccc23"                                                    
OTO SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "c1cncc2c1n(nc2C#N)C(=O)C3CC3"                                                    
OTO SMILES           "OpenEye OEToolkits" 3.1.0.0 "c1cncc2c1n(nc2C#N)C(=O)C3CC3"                                                    
# 
_pdbx_chem_comp_identifier.comp_id           OTO 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   3.1.0.0 
_pdbx_chem_comp_identifier.identifier        "1-cyclopropylcarbonylpyrazolo[4,3-c]pyridine-3-carbonitrile" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
OTO "Create component" 2022-09-20 PDBE 
OTO "Initial release"  2023-09-20 RCSB 
OTO "Modify PCM"       2024-09-27 PDBE 
# 
_pdbx_chem_comp_pcm.pcm_id                             1 
_pdbx_chem_comp_pcm.comp_id                            OTO 
_pdbx_chem_comp_pcm.modified_residue_id                SER 
_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               C3 
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom   OG 
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession     ? 
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession      ? 
# 
