Bioactivity-Guided Discovery of Human Carboxylesterase Inhibitors from the Roots of Paeonia lactiflora
Zhang, Jing-Fang; Zhong, Wan-Chao; Li, Yan-Cheng; Song, Yun-Qing; Xia, Gui-Yang; Tian, Gui-Hua; Ge, Guang-Bo; Lin, Sheng; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00464

data_1559131
_publ_section_title
;
 Bioactivity-Guided Discovery of Human Carboxylesterase Inhibitors from
 the Roots of Paeonia lactiflora
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00464
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                74.596(6)
_cell_angle_beta                 86.938(9)
_cell_angle_gamma                68.597(9)
_cell_formula_units_Z            2
_cell_length_a                   8.6358(13)
_cell_length_b                   9.3834(15)
_cell_length_c                   9.8633(15)
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.099
_cell_measurement_theta_min      4.05
_cell_volume                     716.6(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.02
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16803
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.232
_diffrn_reflns_theta_min         4.049
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1553 before and 0.1013 after correction. The Ratio of minimum to maximum transmission is 0.7451. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 1939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5215
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0666
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1286P)^2^+0.1323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1808
_refine_ls_wR_factor_ref         0.1881
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                4760
_reflns_number_total             5215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00464_si_002.cif
_cod_data_source_block           mj19144
_cod_database_code               1559131
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O2-H2
 0.85 with sigma of 0.02
 C15-H2
 2 with sigma of 0.02
 O2A-H2AA
 0.85 with sigma of 0.02
 O3-H3
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C10(H10), C1A(H1A), C4A(H4A), C5A(H5A), C10A(H10A)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C2A(H2AB,
 H2AC), C3A(H3AB,H3AC), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C14A(H14C,H14D)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C6A(H6A)
3.d Tetrahedral OH refined with riding coordinates:
 O3A(H3AA)
3.e X=CH2 refined with riding coordinates:
 C13(H13A,H13B), C13A(H13C,H13D)
3.f Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
;
_shelx_res_checksum              37893
_shelx_hkl_checksum              44677
_olex2_submission_special_instructions 'No special instructions were received'