data_KSH
# 
_chem_comp.id                                    KSH 
_chem_comp.name                                  "2-[(3,5-dimethoxyphenyl)amino]-5-ethyl-7-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H28 N6 O4" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2010-01-12 
_chem_comp.pdbx_modified_date                    2011-06-04 
_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                        440.496 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     KSH 
_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        3AC3 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
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 
KSH N1   N1   N 0 1 Y N N 5.556  1.450  -7.785  1.496  0.264  -0.208 N1   KSH 1  
KSH C2   C2   C 0 1 Y N N 5.242  2.416  -6.907  2.310  -0.823 -0.366 C2   KSH 2  
KSH C3   C3   C 0 1 Y N N 3.910  2.532  -6.503  3.680  -0.637 -0.366 C3   KSH 3  
KSH C4   C4   C 0 1 Y N N 2.932  1.667  -7.002  4.189  0.647  -0.206 C4   KSH 4  
KSH N5   N5   N 0 1 Y N N 3.281  0.709  -7.886  3.371  1.671  -0.055 N5   KSH 5  
KSH C6   C6   C 0 1 Y N N 4.584  0.647  -8.236  2.048  1.504  -0.054 C6   KSH 6  
KSH C7   C7   C 0 1 Y N N 5.267  -0.275 -9.163  0.979  2.412  0.086  C7   KSH 7  
KSH C8   C8   C 0 1 Y N N 6.685  0.151  -9.134  -0.213 1.655  0.007  C8   KSH 8  
KSH N9   N9   N 0 1 Y N N 6.861  1.204  -8.291  0.104  0.395  -0.171 N9   KSH 9  
KSH C10  C10  C 0 1 N N N 4.541  -1.348 -9.899  1.082  3.857  0.275  C10  KSH 10 
KSH O11  O11  O 0 1 N N N 5.168  -2.137 -10.581 1.107  4.598  -0.691 O11  KSH 11 
KSH N12  N12  N 0 1 N N N 3.216  -1.415 -9.791  1.151  4.370  1.520  N12  KSH 12 
KSH N16  N16  N 0 1 N N N 7.669  -0.442 -9.851  -1.507 2.163  0.097  N16  KSH 13 
KSH C17  C17  C 0 1 Y N N 8.961  -0.050 -9.754  -2.600 1.292  0.118  C17  KSH 14 
KSH C18  C18  C 0 1 Y N N 9.378  0.768  -8.706  -2.461 0.016  0.648  C18  KSH 15 
KSH C19  C19  C 0 1 Y N N 10.710 1.167  -8.612  -3.546 -0.847 0.668  C19  KSH 16 
KSH C20  C20  C 0 1 Y N N 11.628 0.748  -9.570  -4.769 -0.436 0.158  C20  KSH 17 
KSH C21  C21  C 0 1 Y N N 11.219 -0.070 -10.618 -4.908 0.838  -0.371 C21  KSH 18 
KSH C22  C22  C 0 1 Y N N 9.886  -0.469 -10.709 -3.826 1.705  -0.386 C22  KSH 19 
KSH O26  O26  O 0 1 N N N 12.132 -0.478 -11.558 -6.107 1.239  -0.871 O26  KSH 20 
KSH C27  C27  C 0 1 N N N 13.297 -1.203 -11.163 -7.180 0.297  -0.818 C27  KSH 21 
KSH O31  O31  O 0 1 N N N 11.119 1.972  -7.578  -3.411 -2.096 1.186  O31  KSH 22 
KSH C32  C32  C 0 1 N N N 12.181 1.560  -6.716  -4.570 -2.932 1.174  C32  KSH 23 
KSH C37  C37  C 0 1 N N N 1.491  1.804  -6.561  5.679  0.870  -0.202 C37  KSH 24 
KSH C38  C38  C 0 1 N N N 0.818  0.447  -6.519  5.972  2.360  -0.011 C38  KSH 25 
KSH N42  N42  N 0 1 N N N 6.206  3.295  -6.381  1.774  -2.082 -0.522 N42  KSH 26 
KSH C43  C43  C 0 1 N N N 6.154  3.760  -4.998  0.336  -2.407 -0.539 C43  KSH 27 
KSH C44  C44  C 0 1 N N N 7.518  4.396  -4.762  0.240  -3.735 -1.331 C44  KSH 28 
KSH C45  C45  C 0 1 N N N 8.278  4.366  -6.078  1.523  -4.472 -0.862 C45  KSH 29 
KSH C46  C46  C 0 1 N N R 7.337  3.818  -7.145  2.541  -3.323 -0.706 C46  KSH 30 
KSH C53  C53  C 0 1 N N N 6.777  4.972  -7.972  3.423  -3.575 0.518  C53  KSH 31 
KSH O55  O55  O 0 1 N N N 7.545  6.162  -7.744  2.597  -3.812 1.660  O55  KSH 32 
KSH H3   H3   H 0 1 N N N 3.632  3.300  -5.796  4.346  -1.478 -0.489 H3   KSH 33 
KSH HN12 HN12 H 0 0 N N N 2.710  -2.127 -10.278 1.131  3.780  2.289  HN12 KSH 34 
KSH HN1A HN1A H 0 0 N N N 2.727  -0.753 -9.223  1.219  5.330  1.646  HN1A KSH 35 
KSH HN16 HN16 H 0 0 N N N 7.434  -1.191 -10.470 -1.649 3.121  0.146  HN16 KSH 36 
KSH H18  H18  H 0 1 N N N 8.666  1.094  -7.963  -1.509 -0.304 1.044  H18  KSH 37 
KSH H20  H20  H 0 1 N N N 12.660 1.058  -9.500  -5.614 -1.109 0.174  H20  KSH 38 
KSH H22  H22  H 0 1 N N N 9.569  -1.105 -11.522 -3.936 2.699  -0.794 H22  KSH 39 
KSH H27  H27  H 0 1 N N N 13.901 -1.439 -12.051 -7.371 0.023  0.220  H27  KSH 40 
KSH H27A H27A H 0 0 N N N 13.891 -0.592 -10.468 -8.076 0.743  -1.248 H27A KSH 41 
KSH H27B H27B H 0 0 N N N 12.996 -2.137 -10.666 -6.909 -0.594 -1.385 H27B KSH 42 
KSH H32  H32  H 0 1 N N N 12.359 2.335  -5.956  -5.364 -2.460 1.751  H32  KSH 43 
KSH H32A H32A H 0 0 N N N 11.906 0.617  -6.220  -4.904 -3.076 0.146  H32A KSH 44 
KSH H32B H32B H 0 0 N N N 13.096 1.410  -7.308  -4.325 -3.898 1.615  H32B KSH 45 
KSH H37  H37  H 0 1 N N N 1.462  2.252  -5.557  6.129  0.304  0.613  H37  KSH 46 
KSH H37A H37A H 0 0 N N N 0.956  2.450  -7.273  6.098  0.537  -1.152 H37A KSH 47 
KSH H38  H38  H 0 1 N N N -0.227 0.565  -6.197  5.522  2.926  -0.826 H38  KSH 48 
KSH H38A H38A H 0 0 N N N 0.844  -0.006 -7.521  5.553  2.693  0.938  H38A KSH 49 
KSH H38B H38B H 0 0 N N N 1.349  -0.204 -5.809  7.050  2.521  -0.009 H38B KSH 50 
KSH H43  H43  H 0 1 N N N 5.344  4.490  -4.854  -0.034 -2.544 0.477  H43  KSH 51 
KSH H43A H43A H 0 0 N N N 5.979  2.925  -4.304  -0.224 -1.622 -1.046 H43A KSH 52 
KSH H44  H44  H 0 1 N N N 7.396  5.435  -4.421  -0.655 -4.292 -1.053 H44  KSH 53 
KSH H44A H44A H 0 0 N N N 8.069  3.832  -3.995  0.266  -3.553 -2.405 H44A KSH 54 
KSH H45  H45  H 0 1 N N N 8.605  5.381  -6.348  1.352  -4.973 0.091  H45  KSH 55 
KSH H45A H45A H 0 0 N N N 9.163  3.719  -5.988  1.858  -5.182 -1.618 H45A KSH 56 
KSH H46  H46  H 0 1 N N N 7.840  3.090  -7.799  3.158  -3.248 -1.602 H46  KSH 57 
KSH H53  H53  H 0 1 N N N 6.824  4.709  -9.039  4.053  -4.446 0.338  H53  KSH 58 
KSH H53A H53A H 0 0 N N N 5.732  5.153  -7.680  4.052  -2.704 0.699  H53A KSH 59 
KSH HO55 HO55 H 0 0 N N N 7.189  6.874  -8.263  3.091  -3.980 2.474  HO55 KSH 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 
KSH N1  C2   SING Y N 1  
KSH N1  C6   SING Y N 2  
KSH N1  N9   SING Y N 3  
KSH C2  C3   DOUB Y N 4  
KSH C2  N42  SING N N 5  
KSH C3  C4   SING Y N 6  
KSH C4  N5   DOUB Y N 7  
KSH C4  C37  SING N N 8  
KSH N5  C6   SING Y N 9  
KSH C6  C7   DOUB Y N 10 
KSH C7  C8   SING Y N 11 
KSH C7  C10  SING N N 12 
KSH C8  N9   DOUB Y N 13 
KSH C8  N16  SING N N 14 
KSH C10 O11  DOUB N N 15 
KSH C10 N12  SING N N 16 
KSH N16 C17  SING N N 17 
KSH C17 C18  DOUB Y N 18 
KSH C17 C22  SING Y N 19 
KSH C18 C19  SING Y N 20 
KSH C19 C20  DOUB Y N 21 
KSH C19 O31  SING N N 22 
KSH C20 C21  SING Y N 23 
KSH C21 C22  DOUB Y N 24 
KSH C21 O26  SING N N 25 
KSH O26 C27  SING N N 26 
KSH O31 C32  SING N N 27 
KSH C37 C38  SING N N 28 
KSH N42 C43  SING N N 29 
KSH N42 C46  SING N N 30 
KSH C43 C44  SING N N 31 
KSH C44 C45  SING N N 32 
KSH C45 C46  SING N N 33 
KSH C46 C53  SING N N 34 
KSH C53 O55  SING N N 35 
KSH C3  H3   SING N N 36 
KSH N12 HN12 SING N N 37 
KSH N12 HN1A SING N N 38 
KSH N16 HN16 SING N N 39 
KSH C18 H18  SING N N 40 
KSH C20 H20  SING N N 41 
KSH C22 H22  SING N N 42 
KSH C27 H27  SING N N 43 
KSH C27 H27A SING N N 44 
KSH C27 H27B SING N N 45 
KSH C32 H32  SING N N 46 
KSH C32 H32A SING N N 47 
KSH C32 H32B SING N N 48 
KSH C37 H37  SING N N 49 
KSH C37 H37A SING N N 50 
KSH C38 H38  SING N N 51 
KSH C38 H38A SING N N 52 
KSH C38 H38B SING N N 53 
KSH C43 H43  SING N N 54 
KSH C43 H43A SING N N 55 
KSH C44 H44  SING N N 56 
KSH C44 H44A SING N N 57 
KSH C45 H45  SING N N 58 
KSH C45 H45A SING N N 59 
KSH C46 H46  SING N N 60 
KSH C53 H53  SING N N 61 
KSH C53 H53A SING N N 62 
KSH O55 HO55 SING N N 63 
# 
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 
KSH SMILES_CANONICAL CACTVS               3.352 "CCc1cc(N2CCC[C@@H]2CO)n3nc(Nc4cc(OC)cc(OC)c4)c(C(N)=O)c3n1"                                                                                                                         
KSH SMILES           CACTVS               3.352 "CCc1cc(N2CCC[CH]2CO)n3nc(Nc4cc(OC)cc(OC)c4)c(C(N)=O)c3n1"                                                                                                                           
KSH SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "CCc1cc(n2c(n1)c(c(n2)Nc3cc(cc(c3)OC)OC)C(=O)N)N4CCC[C@@H]4CO"                                                                                                                       
KSH SMILES           "OpenEye OEToolkits" 1.7.0 "CCc1cc(n2c(n1)c(c(n2)Nc3cc(cc(c3)OC)OC)C(=O)N)N4CCCC4CO"                                                                                                                            
KSH InChI            InChI                1.03  "InChI=1S/C22H28N6O4/c1-4-13-10-18(27-7-5-6-15(27)12-29)28-22(25-13)19(20(23)30)21(26-28)24-14-8-16(31-2)11-17(9-14)32-3/h8-11,15,29H,4-7,12H2,1-3H3,(H2,23,30)(H,24,26)/t15-/m1/s1" 
KSH InChIKey         InChI                1.03  ITADTXCJWWSRJO-OAHLLOKOSA-N                                                                                                                                                          
# 
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 
KSH "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "2-[(3,5-dimethoxyphenyl)amino]-5-ethyl-7-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
KSH "Create component"     2010-01-12 PDBJ 
KSH "Modify aromatic_flag" 2011-06-04 RCSB 
KSH "Modify descriptor"    2011-06-04 RCSB 
# 
