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_1563992
_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         'C28 H38 N2 O9'
_chemical_formula_sum            'C28 H38 N2 O9'
_chemical_formula_weight         546.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.9810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.9190(2)
_cell_length_b                   7.75040(10)
_cell_length_c                   18.6290(2)
_cell_measurement_reflns_used    13285
_cell_measurement_temperature    99.9(10)
_cell_measurement_theta_max      73.3110
_cell_measurement_theta_min      5.5730
_cell_volume                     2006.94(4)
_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      99.9(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_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    -14.00  36.70   0.30    1.00    --    0.00  57.00 -30.00  169
  2  \w    -32.00  18.70   0.30    1.00    --    0.00 -82.00  90.00  169
  3  \w    -14.00  30.70   0.30    1.00    --    0.00 -82.00 -60.00  149
  4  \w    -25.00  27.50   0.30    1.00    --    0.00 -82.00   0.00  175
  5  \w    -15.00  21.00   0.30    1.00    --    0.00 -82.00 120.00  120
  6  \w     57.00  88.80   0.30    1.00    --    0.00  57.00  30.00  106
  7  \w    -10.00  30.50   0.30    1.00    --    0.00 -82.00 150.00  135
  8  \w    -13.00  17.00   0.30    1.00    --    0.00  57.00  30.00  100
  9  \w     69.00  97.20   0.30    5.95    --   95.20  69.00 -82.10   94
 10  \w    152.00 180.20   0.30    5.95    --   95.20  70.00 -27.54   94
 11  \w     73.00 101.20   0.30    5.95    --   95.20  58.00 -73.14   94
 12  \w     68.00  96.20   0.30    5.95    --   95.20  71.00 -47.69   94
 13  \w    152.00 180.50   0.30    5.95    --   95.20  71.00 -47.69   95
 14  \w     67.00  95.20   0.30    5.95    --   95.20  74.00-117.63   94
 15  \w    150.00 178.20   0.30    5.95    --   95.20  52.00 -80.11   94
 16  \w     69.00  99.00   0.30    5.95    --   95.20  70.00 -27.54  100
 17  \w    113.00 184.40   0.30    5.95    --   95.20  72.00 -56.60  238
 18  \w    159.00 185.10   0.30    5.95    --   95.20  45.00 -15.95   87
 19  \w    118.00 184.00   0.30    5.95    --   95.20  77.00-150.00  220
 20  \w      7.00 117.10   0.30    5.95    --   95.20 -61.00 -60.00  367
 21  \w     81.00 111.00   0.30    5.95    --   95.20  30.00 -30.00  100
 22  \w     77.00 103.70   0.30    5.95    --   95.20  45.00-120.00   89
 23  \w      6.00 120.00   0.30    5.95    --   95.20 -82.00 -60.00  380
 24  \w    104.00 178.40   0.30    5.95    --   95.20  15.00  60.00  248
 25  \w     72.00  98.70   0.30    5.95    --   95.20  61.00 -60.00   89
 26  \w     68.00  94.70   0.30    5.95    --   95.20  72.00 -56.60   89
 27  \w     78.00 106.20   0.30    5.95    --   95.20  45.00 -30.00   94
 28  \w     73.00  98.80   0.30    5.95    --   95.20  61.00-150.00   86
 29  \w     15.00  45.00   0.30    5.95    --   95.20 -77.00 -90.00  100
 30  \w     68.00  96.20   0.30    5.95    --   95.20 -77.00 -90.00   94
 31  \w     75.00 111.00   0.30    5.95    --   95.20  58.00 -16.02  120
 32  \w     73.00  99.70   0.30    5.95    --   95.20  61.00 -90.00   89
 33  \w     71.00  99.20   0.30    5.95    --   95.20  65.00-111.13   94
 34  \w     73.00  98.80   0.30    5.95    --   95.20  61.00 -30.00   86
 35  \w     74.00 102.20   0.30    5.95    --   95.20  56.00-102.67   94
 36  \w    123.00 183.00   0.30    5.95    --   95.20  56.00-102.67  200
 37  \w     79.00 107.20   0.30    5.95    --   95.20  30.00 -90.00   94
 38  \w     76.00 104.20   0.30    5.95    --   95.20  45.00 -60.00   94
 39  \w    148.00 174.10   0.30    5.95    --   95.20  74.00-117.63   87
 40  \w    117.00 184.50   0.30    5.95    --   95.20  69.00 -82.10  225
 41  \w     77.00 143.00   0.30    5.95    --   95.20  45.00 -15.95  220
 42  \w     81.00 127.50   0.30    5.95    --   95.20  30.00-120.00  155
 43  \w    109.00 137.20   0.30    5.95    --   95.20  52.00 -80.11   94
 44  \w     90.00 115.80   0.30    5.95    --   95.20  45.00   0.00   86
 45  \w     72.00 100.20   0.30    5.95    --   95.20  61.00-120.00   94
 46  \w     74.00 106.70   0.30    5.95    --   95.20  52.00 -80.11  109
;
_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      0.0638588000
_diffrn_orient_matrix_UB_12      0.0268974000
_diffrn_orient_matrix_UB_13      -0.0642407000
_diffrn_orient_matrix_UB_21      -0.0822839000
_diffrn_orient_matrix_UB_22      -0.0649511000
_diffrn_orient_matrix_UB_23      -0.0515485000
_diffrn_orient_matrix_UB_31      -0.0378668000
_diffrn_orient_matrix_UB_32      0.1858977000
_diffrn_orient_matrix_UB_33      -0.0086417000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27372
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.041
_diffrn_reflns_theta_min         3.869
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64573
_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 reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.905
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2606 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         7754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0952P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1361
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                6694
_reflns_number_total             7754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00297_si_002.cif
_cod_data_source_block           xieyuhui_wc-161_collect
_cod_database_code               1563992
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.92
_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), C10(H10), C12(H12), C14(H14), C6(H6A)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N22(H22), C9(H9), C3(H3), C19(H19), C5(H5), C4(H4A)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O4(H4)
;
_shelx_res_checksum              2456
_shelx_hkl_checksum              75900
_shelx_fab_checksum              36992
_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 1.748
_oxdiff_exptl_absorpt_empirical_full_min 0.423