data_A1L3N
# 
_chem_comp.id                                    A1L3N 
_chem_comp.name                                  "(+)-SHIN-2" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H26 N4 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         "(4~{R})-6-azanyl-4-[3-(hydroxymethyl)-5-(5-oxidanylpent-1-ynyl)phenyl]-3-methyl-4-propan-2-yl-1~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile" 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2024-08-16 
_chem_comp.pdbx_modified_date                    2024-10-04 
_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                        406.478 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     A1L3N 
_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        9J4G 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
_chem_comp.pdbx_pcm                              ? 
# 
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_n_terminal_atom_flag 
_chem_comp_atom.pdbx_backbone_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 
A1L3N C10  C1  C 0 1 N N N N N N -11.411 23.246 24.701 2.245  1.242  2.428  C10  A1L3N 1  
A1L3N N12  N1  N 0 1 N N N N N N -9.942  25.249 23.153 4.540  -0.156 2.363  N12  A1L3N 2  
A1L3N C13  C2  C 0 1 Y N N N N N -9.970  22.023 26.755 0.518  -0.133 0.200  C13  A1L3N 3  
A1L3N C15  C3  C 0 1 Y N N N N N -11.643 20.685 27.877 -0.498 -2.235 0.754  C15  A1L3N 4  
A1L3N C17  C4  C 0 1 Y N N N N N -10.705 22.604 28.964 -1.874 -0.346 0.199  C17  A1L3N 5  
A1L3N C20  C5  C 0 1 N N N N N N -8.475  21.488 23.202 2.624  3.009  -0.413 C20  A1L3N 6  
A1L3N C21  C6  C 0 1 N N N N N N -6.718  21.314 27.861 1.012  0.993  -3.123 C21  A1L3N 7  
A1L3N C22  C7  C 0 1 N N N N N N -12.545 19.448 27.776 -0.363 -3.683 1.149  C22  A1L3N 8  
A1L3N C24  C8  C 0 1 N N N N N N -10.591 23.544 30.154 -3.170 0.230  0.006  C24  A1L3N 9  
A1L3N C26  C9  C 0 1 N N N N N N -10.621 25.364 32.159 -5.566 1.295  -0.351 C26  A1L3N 10 
A1L3N C28  C10 C 0 1 N N N N N N -11.696 27.720 32.521 -8.025 0.853  -0.290 C28  A1L3N 11 
A1L3N C01  C11 C 0 1 N N R N N N -9.104  22.308 25.503 1.757  0.703  0.004  C01  A1L3N 12 
A1L3N C02  C12 C 0 1 Y N N N N N -7.696  22.830 25.908 2.526  0.201  -1.191 C02  A1L3N 13 
A1L3N C03  C13 C 0 1 Y N N N N N -7.161  23.976 25.269 3.705  -0.480 -1.076 C03  A1L3N 14 
A1L3N C05  C14 C 0 1 N N N N N N -9.239  24.564 24.205 3.803  -0.107 1.206  C05  A1L3N 15 
A1L3N C06  C15 C 0 1 N N N N N N -9.898  23.343 24.761 2.645  0.589  1.218  C06  A1L3N 16 
A1L3N C07  C16 C 0 1 Y N N N N N -6.685  22.474 26.869 2.224  0.313  -2.541 C07  A1L3N 17 
A1L3N C14  C17 C 0 1 Y N N N N N -10.856 20.957 26.775 0.634  -1.460 0.573  C14  A1L3N 18 
A1L3N C16  C18 C 0 1 Y N N N N N -11.580 21.517 28.986 -1.750 -1.688 0.564  C16  A1L3N 19 
A1L3N C18  C19 C 0 1 Y N N N N N -9.915  22.866 27.852 -0.728 0.428  0.012  C18  A1L3N 20 
A1L3N C19  C20 C 0 1 N N N N N N -9.049  21.086 24.570 1.363  2.165  -0.213 C19  A1L3N 21 
A1L3N C25  C21 C 0 1 N N N N N N -10.526 24.299 31.064 -4.233 0.702  -0.153 C25  A1L3N 22 
A1L3N C27  C22 C 0 1 N N N N N N -11.507 26.498 31.615 -6.639 0.237  -0.083 C27  A1L3N 23 
A1L3N C30  C23 C 0 1 N N N N N N -8.291  19.869 25.118 0.598  2.674  1.010  C30  A1L3N 24 
A1L3N N08  N2  N 0 1 Y N N N N N -5.696  23.351 26.743 3.179  -0.275 -3.222 N08  A1L3N 25 
A1L3N N09  N3  N 0 1 Y N N N N N -5.964  24.237 25.790 4.122  -0.783 -2.315 N09  A1L3N 26 
A1L3N N11  N4  N 0 1 N N N N N N -12.535 23.173 24.694 1.929  1.759  3.388  N11  A1L3N 27 
A1L3N O04  O1  O 0 1 N N N N N N -7.851  24.660 24.217 4.278  -0.756 0.123  O04  A1L3N 28 
A1L3N O23  O2  O 0 1 N N N N N N -13.048 19.090 29.020 -0.276 -4.491 -0.026 O23  A1L3N 29 
A1L3N O29  O3  O 0 1 N N N N N N -12.753 27.466 33.419 -9.027 -0.134 -0.039 O29  A1L3N 30 
A1L3N H121 H1  H 0 0 N N N N N N -9.285  25.714 22.560 4.225  0.301  3.158  H121 A1L3N 31 
A1L3N H122 H2  H 0 0 N N N N N N -10.465 24.587 22.616 5.374  -0.651 2.386  H122 A1L3N 32 
A1L3N H201 H3  H 0 0 N N N N N N -8.441  20.607 22.545 3.122  2.704  -1.334 H201 A1L3N 33 
A1L3N H203 H4  H 0 0 N N N N N N -9.115  22.259 22.748 2.350  4.062  -0.480 H203 A1L3N 34 
A1L3N H202 H5  H 0 0 N N N N N N -7.458  21.886 23.334 3.297  2.861  0.431  H202 A1L3N 35 
A1L3N H212 H6  H 0 0 N N N N N N -5.794  21.315 28.458 1.258  2.025  -3.373 H212 A1L3N 36 
A1L3N H213 H7  H 0 0 N N N N N N -7.586  21.427 28.528 0.697  0.466  -4.024 H213 A1L3N 37 
A1L3N H211 H8  H 0 0 N N N N N N -6.798  20.364 27.312 0.202  0.979  -2.394 H211 A1L3N 38 
A1L3N H222 H9  H 0 0 N N N N N N -13.384 19.670 27.100 0.539  -3.814 1.747  H222 A1L3N 39 
A1L3N H221 H10 H 0 0 N N N N N N -11.960 18.609 27.371 -1.233 -3.984 1.733  H221 A1L3N 40 
A1L3N H262 H11 H 0 0 N N N N N N -11.073 24.934 33.065 -5.699 2.130  0.337  H262 A1L3N 41 
A1L3N H261 H12 H 0 0 N N N N N N -9.619  25.750 32.397 -5.656 1.651  -1.377 H261 A1L3N 42 
A1L3N H282 H13 H 0 0 N N N N N N -10.770 27.908 33.085 -8.157 1.688  0.398  H282 A1L3N 43 
A1L3N H281 H14 H 0 0 N N N N N N -11.937 28.601 31.907 -8.115 1.210  -1.316 H281 A1L3N 44 
A1L3N H141 H15 H 0 0 N N N N N N -10.933 20.322 25.905 1.611  -1.894 0.722  H141 A1L3N 45 
A1L3N H161 H16 H 0 0 N N N N N N -12.198 21.327 29.851 -2.633 -2.296 0.698  H161 A1L3N 46 
A1L3N H181 H17 H 0 0 N N N N N N -9.260  23.725 27.843 -0.817 1.464  -0.279 H181 A1L3N 47 
A1L3N H191 H18 H 0 0 N N N N N N -10.088 20.767 24.400 0.729  2.244  -1.097 H191 A1L3N 48 
A1L3N H271 H19 H 0 0 N N N N N N -11.059 26.848 30.673 -6.506 -0.598 -0.771 H271 A1L3N 49 
A1L3N H272 H20 H 0 0 N N N N N N -12.502 26.076 31.413 -6.549 -0.119 0.943  H272 A1L3N 50 
A1L3N H302 H21 H 0 0 N N N N N N -8.313  19.058 24.375 -0.062 1.889  1.379  H302 A1L3N 51 
A1L3N H301 H22 H 0 0 N N N N N N -7.247  20.149 25.324 1.305  2.952  1.791  H301 A1L3N 52 
A1L3N H303 H23 H 0 0 N N N N N N -8.769  19.528 26.048 0.004  3.545  0.731  H303 A1L3N 53 
A1L3N H231 H25 H 0 0 N N N N N N -13.602 18.323 28.930 -0.187 -5.437 0.152  H231 A1L3N 54 
A1L3N H291 H26 H 0 0 N N N N N N -12.877 28.219 33.985 -9.932 0.187  -0.152 H291 A1L3N 55 
A1L3N H1   H27 H 0 1 N N N N N N -5.361  24.983 25.508 4.932  -1.265 -2.544 H1   A1L3N 56 
# 
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 
A1L3N C01 C02  SING N N 1  
A1L3N C02 C03  DOUB Y N 2  
A1L3N C03 O04  SING N N 3  
A1L3N O04 C05  SING N N 4  
A1L3N C05 C06  DOUB N N 5  
A1L3N C06 C01  SING N N 6  
A1L3N C02 C07  SING Y N 7  
A1L3N C07 N08  DOUB Y N 8  
A1L3N N08 N09  SING Y N 9  
A1L3N N09 C03  SING Y N 10 
A1L3N C06 C10  SING N N 11 
A1L3N C10 N11  TRIP N N 12 
A1L3N C05 N12  SING N N 13 
A1L3N C01 C13  SING N N 14 
A1L3N C13 C14  DOUB Y N 15 
A1L3N C14 C15  SING Y N 16 
A1L3N C15 C16  DOUB Y N 17 
A1L3N C16 C17  SING Y N 18 
A1L3N C17 C18  DOUB Y N 19 
A1L3N C18 C13  SING Y N 20 
A1L3N C01 C19  SING N N 21 
A1L3N C19 C20  SING N N 22 
A1L3N C07 C21  SING N N 23 
A1L3N C15 C22  SING N N 24 
A1L3N C22 O23  SING N N 25 
A1L3N C17 C24  SING N N 26 
A1L3N C24 C25  TRIP N N 27 
A1L3N C25 C26  SING N N 28 
A1L3N C26 C27  SING N N 29 
A1L3N C27 C28  SING N N 30 
A1L3N C28 O29  SING N N 31 
A1L3N C19 C30  SING N N 32 
A1L3N N12 H121 SING N N 33 
A1L3N N12 H122 SING N N 34 
A1L3N C20 H201 SING N N 35 
A1L3N C20 H203 SING N N 36 
A1L3N C20 H202 SING N N 37 
A1L3N C21 H212 SING N N 38 
A1L3N C21 H213 SING N N 39 
A1L3N C21 H211 SING N N 40 
A1L3N C22 H222 SING N N 41 
A1L3N C22 H221 SING N N 42 
A1L3N C26 H262 SING N N 43 
A1L3N C26 H261 SING N N 44 
A1L3N C28 H282 SING N N 45 
A1L3N C28 H281 SING N N 46 
A1L3N C14 H141 SING N N 47 
A1L3N C16 H161 SING N N 48 
A1L3N C18 H181 SING N N 49 
A1L3N C19 H191 SING N N 50 
A1L3N C27 H271 SING N N 51 
A1L3N C27 H272 SING N N 52 
A1L3N C30 H302 SING N N 53 
A1L3N C30 H301 SING N N 54 
A1L3N C30 H303 SING N N 55 
A1L3N O23 H231 SING N N 56 
A1L3N O29 H291 SING N N 57 
A1L3N N09 H1   SING N N 58 
# 
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 
A1L3N InChI            InChI                1.06  "InChI=1S/C23H26N4O3/c1-14(2)23(19(12-24)21(25)30-22-20(23)15(3)26-27-22)18-10-16(7-5-4-6-8-28)9-17(11-18)13-29/h9-11,14,28-29H,4,6,8,13,25H2,1-3H3,(H,26,27)/t23-/m0/s1" 
A1L3N InChIKey         InChI                1.06  IWUCUJZMKDHLOF-QHCPKHFHSA-N                                                                                                                                               
A1L3N SMILES_CANONICAL CACTVS               3.385 "CC(C)[C@]1(c2cc(CO)cc(c2)C#CCCCO)C(=C(N)Oc3[nH]nc(C)c13)C#N"                                                                                                             
A1L3N SMILES           CACTVS               3.385 "CC(C)[C]1(c2cc(CO)cc(c2)C#CCCCO)C(=C(N)Oc3[nH]nc(C)c13)C#N"                                                                                                              
A1L3N SMILES_CANONICAL "OpenEye OEToolkits" 2.0.7 "Cc1c2c([nH]n1)OC(=C([C@@]2(c3cc(cc(c3)C#CCCCO)CO)C(C)C)C#N)N"                                                                                                            
A1L3N SMILES           "OpenEye OEToolkits" 2.0.7 "Cc1c2c([nH]n1)OC(=C(C2(c3cc(cc(c3)C#CCCCO)CO)C(C)C)C#N)N"                                                                                                                
# 
_pdbx_chem_comp_identifier.comp_id           A1L3N 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   2.0.7 
_pdbx_chem_comp_identifier.identifier        "(4~{R})-6-azanyl-4-[3-(hydroxymethyl)-5-(5-oxidanylpent-1-ynyl)phenyl]-3-methyl-4-propan-2-yl-1~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile" 
# 
_pdbx_chem_comp_synonyms.ordinal      1 
_pdbx_chem_comp_synonyms.comp_id      A1L3N 
_pdbx_chem_comp_synonyms.name         "(4~{R})-6-azanyl-4-[3-(hydroxymethyl)-5-(5-oxidanylpent-1-ynyl)phenyl]-3-methyl-4-propan-2-yl-1~{H}-pyrano[2,3-c]pyrazole-5-carbonitrile" 
_pdbx_chem_comp_synonyms.provenance   PDB 
_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 
A1L3N "Create component" 2024-08-16 PDBJ 
A1L3N "Initial release"  2024-10-09 RCSB 
# 
