Cyclopentenone-Containing Tetrahydroquinoline and Geldanamycin Alkaloids from Streptomyces malaysiensis as Potential Anti-Androgens against Prostate Cancer Cells
Xie, Yuhui; Guo, Lang; Huang, Jie; Huang, Xiaolong; Cong, Ziwen; Liu, Qianqian; Wang, Qianshu; Pang, Xiaoyan; Xiang, Songtao; Zhou, Xuefeng; Liu, Yonghong; Wang, Junjian; Wang, Junfeng; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.1c00297

data_1563993
_publ_section_title
;
 Cyclopentenone-Containing Tetrahydroquinoline and Geldanamycin Alkaloids
 from Streptomyces malaysiensis as Potential Anti-Androgens against
 Prostate Cancer Cells
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.1c00297
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H40 N2 O9'
_chemical_formula_sum            'C29 H40 N2 O9'
_chemical_formula_weight         560.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.74200(9)
_cell_length_b                   18.7784(2)
_cell_length_c                   20.7717(3)
_cell_measurement_reflns_used    8857
_cell_measurement_temperature    105(7)
_cell_measurement_theta_max      73.6940
_cell_measurement_theta_min      4.8500
_cell_volume                     3019.84(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      105(7)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -13.00  30.00   0.25    0.34    --    0.00 -82.00  30.00  172
  2  \w    -29.00  24.00   0.25    0.34    --    0.00 -82.00 -90.00  212
  3  \w     -5.00  30.00   0.25    0.34    --    0.00  38.00  90.00  140
  4  \w     62.00  89.00   0.25    0.34    --    0.00  38.00  90.00  108
  5  \w      9.00 120.00   0.25    1.38    --   95.20 -82.00   0.00  444
  6  \w      6.00  95.00   0.25    1.38    --   95.20 -30.00 150.00  356
  7  \w     79.00 112.00   0.25    1.38    --   95.20 -30.00   0.00  132
  8  \w     73.00 109.00   0.25    1.38    --   95.20  15.00   0.00  144
  9  \w    112.00 138.00   0.25    1.38    --   95.20  15.00   0.00  104
 10  \w    148.00 178.00   0.25    1.38    --   95.20  15.00   0.00  120
 11  \w     23.00  58.00   0.25    1.38    --   95.20 -30.00   0.00  140
 12  \w     14.00 117.00   0.25    1.38    --   95.20 -61.00   0.00  412
 13  \w     19.00  90.00   0.25    1.38    --   95.20 -45.00 120.00  284
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1233904000
_diffrn_orient_matrix_UB_12      0.0272536000
_diffrn_orient_matrix_UB_13      0.0527140000
_diffrn_orient_matrix_UB_21      0.1484295000
_diffrn_orient_matrix_UB_22      0.0025297000
_diffrn_orient_matrix_UB_23      -0.0493775000
_diffrn_orient_matrix_UB_31      -0.0484205000
_diffrn_orient_matrix_UB_32      0.0772990000
_diffrn_orient_matrix_UB_33      -0.0169670000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14698
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.082
_diffrn_reflns_theta_min         4.257
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         5919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+1.4619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                5450
_reflns_number_total             5919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00297_si_003.cif
_cod_data_source_block           xieyuhui_wc-17351_collect2
_cod_original_cell_volume        3019.84(7)
_cod_database_code               1563993
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.863
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C6(H6), C10(H10), C12(H12), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N22(H22), C9(H9), C19(H19), C3(H3), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C), C28(H28A,H28B,
 H28C), C27(H27A,H27B,H27C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C)
2.e Idealised tetrahedral OH refined as rotating group:
 O33(H33)
;
_shelx_res_checksum              45392
_shelx_hkl_checksum              50852
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.155
_oxdiff_exptl_absorpt_empirical_full_min 0.203