# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May 11 16:40:55 2020
#   Inital geometry file: a 99 line input string
#   Ligand name: 7-hydroxy-N-[(2S)-1-hydroxypropan-2-yl]-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H](CO)NC(=O)c1cnn2c(O)cc(nc12)c3ccccc3
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 KKM  KKM  7-hydroxy-N-[(2S)-1-hydroxypropan-2-yl]-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide  ligand  39  23  .  2021-08-12  2021-08-12  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_KKM
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 KKM  C10   C  CR16  0  -0.280  -3.0270   2.0550  -0.3735
 KKM  C13   C  CR5   0  -0.387   1.3163  -0.6768  -0.1251
 KKM  C17   C  CH2   0  -0.163   5.6646   1.0840  -0.7130
 KKM  C21   C  CR15  0  -0.028   1.7475  -2.0145  -0.1122
 KKM  C02   C  CR6   0   0.661  -1.6120  -2.5903  -0.0258
 KKM  C03   C  CR16  0  -0.514  -2.6234  -1.6666  -0.0200
 KKM  C04   C  CR6   0   0.266  -2.2948  -0.2932  -0.0365
 KKM  C05   C  CR6   0   0.052  -3.3510   0.7407  -0.0282
 KKM  C06   C  CR16  0  -0.322  -4.6687   0.4455   0.3233
 KKM  C07   C  CR16  0  -0.236  -5.6387   1.4369   0.3229
 KKM  C08   C  CR16  0  -0.256  -5.3082   2.7376  -0.0311
 KKM  C09   C  CR16  0  -0.238  -3.9978   3.0427  -0.3786
 KKM  N11   N  N     0  -0.462  -1.0508   0.1364  -0.0727
 KKM  C12   C  CR56  0   0.646  -0.0779  -0.7680  -0.0899
 KKM  N15   N  NH1   0  -0.658   3.4335   0.4120  -0.0618
 KKM  C16   C  CH1   0  -0.112   4.3680   1.5214  -0.0528
 KKM  C19   C  CH3   0  -0.654   4.5788   2.0672   1.3567
 KKM  N23   N  N     0  -0.426  -0.3424  -2.1246  -0.0566
 KKM  N22   N  N     0  -0.288   0.7613  -2.8852  -0.0720
 KKM  H101  H  HCR6  0   0.265  -2.0074   2.2968  -0.6411
 KKM  H171  H  HCH2  0   0.217   5.4553   0.7933  -1.7491
 KKM  H172  H  HCH2  0   0.206   6.3445   1.9445  -0.7472
 KKM  H211  H  HCR5  0   0.278   2.7615  -2.3869  -0.1410
 KKM  H011  H  HOH1  0   0.508  -2.6496  -4.1656   0.0194
 KKM  H031  H  HCR6  0   0.303  -3.6466  -2.0121  -0.0198
 KKM  H061  H  HCR6  0   0.258  -4.9541  -0.5555   0.6182
 KKM  H071  H  HCR6  0   0.264  -6.6540   1.1899   0.6029
 KKM  H081  H  HCR6  0   0.264  -6.0663   3.5095  -0.0341
 KKM  H091  H  HCR6  0   0.262  -3.7302   4.0541  -0.6548
 KKM  H151  H  HNH1  0   0.391   3.8091  -0.4868   0.1957
 KKM  H161  H  HCH1  0   0.253   3.9497   2.3119  -0.6781
 KKM  H181  H  HOH1  0   0.460   6.9165  -0.3857  -0.4992
 KKM  H192  H  HCH3  0   0.227   5.2711   2.9105   1.3438
 KKM  H193  H  HCH3  0   0.236   3.6360   2.4172   1.7764
 KKM  H191  H  HCH3  0   0.227   4.9839   1.3048   2.0223
 KKM  C14   C  C     0   0.510   2.0997   0.5638  -0.1852
 KKM  O01   O  OH1   0  -0.564  -1.7213  -3.8966  -0.0116
 KKM  O18   O  OH1   0  -0.673   6.2149   0.0131   0.0227
 KKM  O20   O  O     0  -0.491   1.5677   1.6549  -0.3526

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 KKM  C17  C16   single    1.519  0.020  1.519
 KKM  C17  O18   single    1.411  0.020  1.411
 KKM  C16  C19   single    1.526  0.020  1.526
 KKM  C16  N15   single    1.451  0.020  1.451
 KKM  O20  C14   double    1.225  0.020  1.225
 KKM  N15  C14   single    1.348  0.020  1.348
 KKM  C14  C13   single    1.469  0.020  1.469
 KKM  C13  C21   aromatic  1.406  0.020  1.406
 KKM  C13  C12   aromatic  1.398  0.020  1.398
 KKM  C21  N22   aromatic  1.316  0.020  1.316
 KKM  C12  N11   aromatic  1.328  0.020  1.328
 KKM  C12  N23   aromatic  1.383  0.020  1.383
 KKM  N11  C04   aromatic  1.317  0.020  1.317
 KKM  C06  C07   aromatic  1.387  0.020  1.387
 KKM  C06  C05   aromatic  1.395  0.020  1.395
 KKM  C07  C08   aromatic  1.388  0.020  1.388
 KKM  N22  N23   aromatic  1.341  0.020  1.341
 KKM  N23  C02   aromatic  1.353  0.020  1.353
 KKM  C04  C05   single    1.478  0.020  1.478
 KKM  C04  C03   aromatic  1.412  0.020  1.412
 KKM  C05  C10   aromatic  1.397  0.020  1.397
 KKM  C08  C09   aromatic  1.390  0.020  1.390
 KKM  C02  C03   aromatic  1.370  0.020  1.370
 KKM  C02  O01   single    1.311  0.020  1.311
 KKM  C10  C09   aromatic  1.385  0.020  1.385
 KKM  C10  H101  single    0.930  0.020  1.080
 KKM  C17  H171  single    0.970  0.020  1.090
 KKM  C17  H172  single    0.970  0.020  1.090
 KKM  C21  H211  single    0.930  0.020  1.080
 KKM  O01  H011  single    0.850  0.020  0.980
 KKM  C03  H031  single    0.930  0.020  1.080
 KKM  C06  H061  single    0.930  0.020  1.080
 KKM  C07  H071  single    0.930  0.020  1.080
 KKM  C08  H081  single    0.930  0.020  1.080
 KKM  C09  H091  single    0.930  0.020  1.080
 KKM  N15  H151  single    0.860  0.020  1.020
 KKM  C16  H161  single    0.970  0.020  1.090
 KKM  O18  H181  single    0.850  0.020  0.980
 KKM  C19  H192  single    0.970  0.020  1.090
 KKM  C19  H193  single    0.970  0.020  1.090
 KKM  C19  H191  single    0.970  0.020  1.090

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 KKM  H101  C10  C09   120.03  3.000
 KKM  H101  C10  C05   119.35  3.000
 KKM  C09   C10  C05   120.62  3.000
 KKM  C14   C13  C12   126.04  3.000
 KKM  C12   C13  C21   104.11  3.000
 KKM  C14   C13  C21   129.85  3.000
 KKM  H172  C17  H171  107.27  3.000
 KKM  H172  C17  O18   111.70  3.000
 KKM  H171  C17  O18   111.47  3.000
 KKM  H172  C17  C16   108.46  3.000
 KKM  H171  C17  C16   108.91  3.000
 KKM  O18   C17  C16   108.95  3.000
 KKM  H211  C21  N22   118.42  3.000
 KKM  H211  C21  C13   128.00  3.000
 KKM  N22   C21  C13   113.58  3.000
 KKM  N23   C02  C03   117.45  3.000
 KKM  C03   C02  O01   127.62  3.000
 KKM  N23   C02  O01   114.93  3.000
 KKM  H031  C03  C04   122.11  3.000
 KKM  H031  C03  C02   118.94  3.000
 KKM  C04   C03  C02   118.95  3.000
 KKM  N11   C04  C05   116.56  3.000
 KKM  C05   C04  C03   120.93  3.000
 KKM  N11   C04  C03   122.51  3.000
 KKM  C06   C05  C04   121.89  3.000
 KKM  C04   C05  C10   119.40  3.000
 KKM  C06   C05  C10   118.70  3.000
 KKM  H061  C06  C07   118.49  3.000
 KKM  H061  C06  C05   120.90  3.000
 KKM  C07   C06  C05   120.61  3.000
 KKM  H071  C07  C08   120.22  3.000
 KKM  H071  C07  C06   119.55  3.000
 KKM  C08   C07  C06   120.23  3.000
 KKM  H081  C08  C09   120.23  3.000
 KKM  H081  C08  C07   120.17  3.000
 KKM  C09   C08  C07   119.60  3.000
 KKM  H091  C09  C08   120.15  3.000
 KKM  H091  C09  C10   119.62  3.000
 KKM  C08   C09  C10   120.24  3.000
 KKM  C12   N11  C04   118.05  3.000
 KKM  N23   C12  N11   121.84  3.000
 KKM  N23   C12  C13   104.80  3.000
 KKM  N11   C12  C13   133.35  3.000
 KKM  H151  N15  C16   116.13  3.000
 KKM  H151  N15  C14   119.52  3.000
 KKM  C16   N15  C14   123.50  3.000
 KKM  H161  C16  C19   108.85  3.000
 KKM  H161  C16  N15   107.67  3.000
 KKM  C19   C16  N15   111.60  3.000
 KKM  H161  C16  C17   106.66  3.000
 KKM  N15   C16  C17   109.09  3.000
 KKM  C19   C16  C17   112.73  3.000
 KKM  H191  C19  H193  108.12  3.000
 KKM  H191  C19  H192  108.18  3.000
 KKM  H193  C19  H192  107.77  3.000
 KKM  H191  C19  C16   111.42  3.000
 KKM  H193  C19  C16   110.55  3.000
 KKM  H192  C19  C16   110.68  3.000
 KKM  N22   N23  C12   113.51  3.000
 KKM  N22   N23  C02   125.29  3.000
 KKM  C12   N23  C02   121.20  3.000
 KKM  N23   N22  C21   104.00  3.000
 KKM  O20   C14  N15   122.85  3.000
 KKM  N15   C14  C13   115.40  3.000
 KKM  O20   C14  C13   121.75  3.000
 KKM  H011  O01  C02   110.95  3.000
 KKM  H181  O18  C17   108.45  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 KKM  CONST_01  C07   C06  C05  C10    0.00   0.0  0
 KKM  CONST_04  C07   C08  C09  C10    0.00   0.0  0
 KKM  CONST_05  N23   N22  C21  C13    0.00   0.0  0
 KKM  CONST_06  C04   N11  C12  C13  180.00   0.0  0
 KKM  CONST_07  N22   N23  C12  C13    0.00   0.0  0
 KKM  CONST_08  C02   N23  C12  C13  180.00   0.0  0
 KKM  CONST_09  N11   C12  C13  C21  180.00   0.0  0
 KKM  CONST_10  N23   C12  C13  C21    0.00   0.0  0
 KKM  CONST_11  C12   N23  N22  C21    0.00   0.0  0
 KKM  CONST_12  C02   N23  N22  C21  180.00   0.0  0
 KKM  CONST_13  N11   C12  N23  C02    0.00   0.0  0
 KKM  CONST_14  N11   C04  C03  C02    0.00   0.0  0
 KKM  CONST_15  C05   C04  C03  C02  180.00   0.0  0
 KKM  CONST_16  C12   N11  C04  C03    0.00   0.0  0
 KKM  CONST_18  C12   N23  C02  C03    0.00   0.0  0
 KKM  CONST_19  N22   N23  C02  C03  180.00   0.0  0
 KKM  CONST_20  N23   C12  N11  C04    0.00   0.0  0
 KKM  CONST_21  C07   C06  C05  C04  180.00   0.0  0
 KKM  CONST_22  C09   C10  C05  C04  180.00   0.0  0
 KKM  CONST_23  N23   C02  C03  C04    0.00   0.0  0
 KKM  CONST_24  C08   C07  C06  C05    0.00   0.0  0
 KKM  CONST_25  C12   N11  C04  C05  180.00   0.0  0
 KKM  CONST_26  C08   C09  C10  C05    0.00   0.0  0
 KKM  CONST_27  C09   C08  C07  C06    0.00   0.0  0
 KKM  CONST_29  C09   C10  C05  C06    0.00   0.0  0
 KKM  CONST_30  N22   N23  C12  N11  180.00   0.0  0
 KKM  CONST_31  N22   C21  C13  C12    0.00   0.0  0
 KKM  CONST_32  C12   N23  C02  O01  180.00   0.0  0
 KKM  CONST_33  N22   N23  C02  O01    0.00   0.0  0
 KKM  CONST_34  C04   C03  C02  O01  180.00   0.0  0
 KKM  CONST_35  C14   C13  C12  N11    0.00   0.0  0
 KKM  CONST_36  N22   C21  C13  C14  180.00   0.0  0
 KKM  CONST_37  N23   C12  C13  C14  180.00   0.0  0
 KKM  CONST_38  H061  C06  C05  C10  180.00   0.0  0
 KKM  CONST_39  H081  C08  C09  C10  180.00   0.0  0
 KKM  CONST_40  H101  C10  C05  C04    0.00   0.0  0
 KKM  CONST_41  H071  C07  C06  C05  180.00   0.0  0
 KKM  CONST_42  H031  C03  C04  C05    0.00   0.0  0
 KKM  CONST_43  H091  C09  C10  C05  180.00   0.0  0
 KKM  CONST_44  H211  C21  C13  C12  180.00   0.0  0
 KKM  CONST_45  C16   N15  C14  C13  180.00   0.0  0
 KKM  CONST_46  H151  N15  C14  C13    0.00   0.0  0
 KKM  CONST_47  O20   C14  N15  C16    0.00   0.0  0
 KKM  Var_01    O20   C14  C13  C21  170.95  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 KKM  chir_01  C16  C17  C19  N15  positiv

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 KKM  plan-1  C10   0.020
 KKM  plan-1  C04   0.020
 KKM  plan-1  C05   0.020
 KKM  plan-1  C06   0.020
 KKM  plan-1  C07   0.020
 KKM  plan-1  C08   0.020
 KKM  plan-1  C09   0.020
 KKM  plan-1  H101  0.020
 KKM  plan-1  H061  0.020
 KKM  plan-1  H071  0.020
 KKM  plan-1  H081  0.020
 KKM  plan-1  H091  0.020
 KKM  plan-2  C13   0.020
 KKM  plan-2  C21   0.020
 KKM  plan-2  C02   0.020
 KKM  plan-2  C03   0.020
 KKM  plan-2  C04   0.020
 KKM  plan-2  C05   0.020
 KKM  plan-2  N11   0.020
 KKM  plan-2  C12   0.020
 KKM  plan-2  N23   0.020
 KKM  plan-2  N22   0.020
 KKM  plan-2  H211  0.020
 KKM  plan-2  H031  0.020
 KKM  plan-2  C14   0.020
 KKM  plan-2  O01   0.020
 KKM  plan-3  C13   0.020
 KKM  plan-3  N15   0.020
 KKM  plan-3  C16   0.020
 KKM  plan-3  H151  0.020
 KKM  plan-3  C14   0.020
 KKM  plan-3  O20   0.020

