Role of hypoxanthine-guanine phosphoribosyltransferase in the metabolism of fairy chemicals in rice.
Takemura, Hirohide; Choi, Jae-Hoon; Fushimi, Keiji; Narikawa, Rei; Wu, Jing; Kondo, Mitsuru; Nelson, David C.; Suzuki, Tomohiro; Ouchi, Hitoshi; Inai, Makoto; Hirai, Hirofumi; Kawagishi, Hirokazu; Organic & biomolecular chemistry 21 (2023) 2556–2561; doi:10.1039/d3ob00026e

data_7159231
_publ_section_title
;
 Role of hypoxanthine-guanine phosphoribosyltransferase in the metabolism
 of fairy chemicals in rice.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2556
_journal_page_last               2561
_journal_paper_doi               10.1039/d3ob00026e
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H11 N5 O6, H2 O'
_chemical_formula_sum            'C9 H13 N5 O7'
_chemical_formula_weight         303.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-08 deposited with the CCDC.	2023-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.3058(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.32005(12)
_cell_length_b                   5.34244(2)
_cell_length_c                   11.81711(4)
_cell_measurement_reflns_used    47235
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.6990
_cell_measurement_theta_min      3.7390
_cell_volume                     1206.924(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -83.00   7.00   0.50    2.00    --  -46.33 103.00 -38.00  180
  2  \w     -7.00  87.00   0.50    2.00    --   50.08-103.00-140.00  188
  3  \w   -177.00 -84.00   0.50    2.00    -- -104.98-103.00-140.00  186
  4  \w   -107.00 -32.00   0.50    2.00    -- -104.98 103.00 -38.00  150
  5  \w     84.00 178.00   0.50    2.00    --  108.73 103.00 -38.00  188
  6  \w     36.00 106.00   0.50    2.00    --  108.73-103.00-140.00  140
  7  \w   -119.00 -73.00   0.50    2.00    --  -46.33-125.00 -60.00   92
  8  \w   -119.00 -73.00   0.50    2.00    --  -46.33-125.00   0.00   92
  9  \w     34.00 122.00   0.50    2.00    --   50.08  57.00 120.00  176
 10  \w     74.00 122.00   0.50    2.00    --   50.08 125.00-180.00   96
 11  \w     34.00 122.00   0.50    2.00    --   50.08  57.00  30.00  176
 12  \w   -106.00 -32.00   0.50    2.00    -- -104.98  77.00 150.00  148
 13  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 150.00  176
 14  \w   -112.00 -32.00   0.50    2.00    -- -104.98 125.00 -30.00  160
 15  \w    -67.00 -32.00   0.50    2.00    -- -104.98  57.00 -60.00   70
 16  \w    -67.00 -32.00   0.50    2.00    -- -104.98  57.00-180.00   70
 17  \w    -67.00 -32.00   0.50    2.00    -- -104.98  57.00 120.00   70
 18  \w   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00  60.00  174
 19  \w     36.00  65.00   0.50    2.00    --  108.73 -57.00 -90.00   58
 20  \w     36.00 111.00   0.50    2.00    --  108.73-125.00 150.00  150
 21  \w     36.00  65.00   0.50    2.00    --  108.73 -57.00 120.00   58
 22  \w     36.00  65.00   0.50    2.00    --  108.73 -57.00  90.00   58
 23  \w     93.00 178.00   0.50    2.00    --  108.73  57.00 -60.00  170
 24  \w     36.00 111.00   0.50    2.00    --  108.73-125.00-180.00  150
 25  \w     36.00 111.00   0.50    2.00    --  108.73-125.00   0.00  150
 26  \w     36.00  65.00   0.50    2.00    --  108.73 -57.00-150.00   58
 27  \w     36.00  65.00   0.50    2.00    --  108.73 -57.00   0.00   58
 28  \w     94.00 178.00   0.50    2.00    --  108.73  38.00  60.00  168
 29  \w     36.00 104.00   0.50    2.00    --  108.73 -77.00-150.00  136
 30  \w     36.00  65.00   0.50    2.00    --  108.73 -57.00  30.00   58
 31  \w   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00 -60.00  192
 32  \w     34.00 122.00   0.50    2.00    --   50.08  57.00-120.00  176
 33  \w     27.00 122.00   0.50    2.00    --   50.08  77.00-120.00  190
 34  \w    -25.00  25.00   0.50    2.00    --   50.08 -19.00  90.00  100
 35  \w     27.00 122.00   0.50    2.00    --   50.08  77.00 150.00  190
 36  \w     27.00 122.00   0.50    2.00    --   50.08  77.00  60.00  190
 37  \w     34.00 122.00   0.50    2.00    --   50.08  57.00 -30.00  176
 38  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00  60.00  192
 39  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 -90.00  176
 40  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00  90.00  192
 41  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 120.00  176
 42  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 -90.00  192
 43  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 -60.00  192
 44  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 -60.00  176
 45  \w   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00-180.00  174
 46  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00-120.00  192
 47  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00-180.00  192
 48  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 120.00  192
 49  \w   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00 -60.00  174
 50  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00  30.00  176
 51  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00-150.00  192
 52  \w     36.00 106.00   0.50    2.00    --  108.73 -99.00  30.00  140
 53  \w     93.00 178.00   0.50    2.00    --  108.73  57.00 150.00  170
 54  \w     85.00 178.00   0.50    2.00    --  108.73  77.00 -30.00  186
 55  \w     94.00 178.00   0.50    2.00    --  108.73  38.00-150.00  168
 56  \w     94.00 178.00   0.50    2.00    --  108.73  38.00 -90.00  168
 57  \w     85.00 178.00   0.50    2.00    --  108.73  77.00 -60.00  186
 58  \w     94.00 178.00   0.50    2.00    --  108.73  38.00-120.00  168
 59  \w   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00 -90.00  192
 60  \w   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00-120.00  192
 61  \w     36.00 124.00   0.50    2.00    --   50.08  38.00  60.00  176
 62  \w     36.00 124.00   0.50    2.00    --   50.08  38.00-120.00  176
 63  \w     27.00 122.00   0.50    2.00    --   50.08  77.00  90.00  190
 64  \w     27.00 122.00   0.50    2.00    --   50.08  77.00   0.00  190
 65  \w     27.00 122.00   0.50    2.00    --   50.08  77.00-180.00  190
 66  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00  60.00  176
 67  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-150.00  290
 68  \w   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00-150.00  174
 69  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 -30.00  192
 70  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-180.00  290
 71  \w   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00 120.00  174
 72  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00  90.00  176
 73  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00  30.00  192
 74  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00 150.00  192
 75  \w   -177.00 -81.00   0.50    2.00    -- -104.98 -77.00   0.00  192
 76  \w   -177.00 -90.00   0.50    2.00    -- -104.98 -38.00  90.00  174
 77  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00   0.00  176
 78  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00-180.00  176
 79  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00-150.00  176
 80  \w   -177.00 -89.00   0.50    2.00    -- -104.98 -57.00 -30.00  176
 81  \w     85.00 178.00   0.50    2.00    --  108.73  77.00-150.00  186
 82  \w     85.00 178.00   0.50    2.00    --  108.73  77.00 150.00  186
 83  \w     85.00 178.00   0.50    2.00    --  108.73  77.00  90.00  186
 84  \w     85.00 178.00   0.50    2.00    --  108.73  77.00-120.00  186
 85  \w     93.00 178.00   0.50    2.00    --  108.73  57.00  90.00  170
 86  \w     94.00 178.00   0.50    2.00    --  108.73  38.00 -60.00  168
 87  \w   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00-150.00  192
 88  \w   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00 -30.00  192
 89  \w   -120.00 -32.00   0.50    2.00    --  -46.33 -38.00 -60.00  176
 90  \w   -119.00 -23.00   0.50    2.00    --  -46.33 -77.00  30.00  192
 91  \w     36.00 124.00   0.50    2.00    --   50.08  38.00 150.00  176
 92  \w     34.00 122.00   0.50    2.00    --   50.08  57.00   0.00  176
 93  \w     27.00 122.00   0.50    2.00    --   50.08  77.00-150.00  190
 94  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  60.00  290
 95  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00   0.00  290
 96  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00   0.00  290
 97  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  30.00  290
 98  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  30.00  290
 99  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 120.00  290
100  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  90.00  290
101  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -30.00  290
102  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-120.00  290
103  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -60.00  290
104  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-150.00  290
105  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-180.00  290
106  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -90.00  290
107  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -60.00  290
108  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -30.00  290
109  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 -90.00  290
110  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 150.00  290
111  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  60.00  290
112  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00  90.00  290
113  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00 120.00  290
114  \w   -177.00 -32.00   0.50    2.00    -- -104.98   0.00-120.00  290
115  \w    -23.00  97.00   0.50    2.00    --   50.08   0.00-150.00  240
116  \w    -23.00 123.00   0.50    2.00    --   50.08   0.00-180.00  292
117  \w     47.00  72.00   0.50    2.00    --  108.73-103.00-140.00   50
118  \w     97.00 123.00   0.50    2.00    --   50.33 125.00 -30.00   52
119  \w     80.00 106.00   0.50    2.00    --  108.73 -99.00  90.00   52
120  \w     36.00  61.00   0.50    2.00    --  108.73 -57.00-120.00   50
121  \w     47.00  72.00   0.50    2.00    --  108.73-103.00-140.00   50
122  \w   -119.00  26.00   0.50    2.00    --  -46.58   0.00-180.00  290
123  \w   -120.00 -32.00   0.50    2.00    --  -46.58 -38.00 120.00  176
124  \w   -118.00 -23.00   0.50    2.00    --  -46.58 -77.00 120.00  190
125  \w   -119.00  26.00   0.50    2.00    --  -46.58   0.00 -60.00  290
126  \w   -119.00  26.00   0.50    2.00    --  -46.58   0.00-120.00  290
127  \w   -119.00  26.00   0.50    2.00    --  -46.58   0.00 -90.00  290
128  \w   -119.00  26.00   0.50    2.00    --  -46.58   0.00-150.00  290
129  \w    -23.00 123.00   0.50    2.00    --   50.08   0.00-180.00  292
130  \w     34.00 123.00   0.50    2.00    --   50.33  57.00  60.00  178
131  \w    -22.00 123.00   0.50    2.00    --   50.33   0.00 -60.00  290
132  \w     27.00 123.00   0.50    2.00    --   50.33  77.00 150.00  192
133  \w    -22.00 123.00   0.50    2.00    --   50.33   0.00  30.00  290
134  \w    -22.00 123.00   0.50    2.00    --   50.33   0.00 -30.00  290
135  \w    -22.00  49.50   0.50    2.00    --   50.33   0.00   0.00  143
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068866000
_diffrn_orient_matrix_UB_12      -0.0018768000
_diffrn_orient_matrix_UB_13      0.1315258000
_diffrn_orient_matrix_UB_21      0.0225155000
_diffrn_orient_matrix_UB_22      0.2768314000
_diffrn_orient_matrix_UB_23      0.0030159000
_diffrn_orient_matrix_UB_31      -0.0770532000
_diffrn_orient_matrix_UB_32      0.0807705000
_diffrn_orient_matrix_UB_33      -0.0072282000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            53776
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.848
_diffrn_reflns_theta_min         3.780
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1106 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0523P)^2^+0.6405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2514
_reflns_number_total             2516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00026e2.cif
_cod_data_source_block           aohr-takemura-210908a_auto
_cod_depositor_comments
;
          Adding full bibliography for 7159231.cif.

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18 H26 N10 O14'
_cod_original_formula_weight         606.49
_cod_original_formula_moiety         '2(C9 H11 N5 O6), 2(H2 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1206.924(9)
_cod_database_code               7159231
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H18N10O10
_diffrn_oxdiff_digest_frames
;
011a030bc60cdd29877739d307a71800eb22022670b
;
_diffrn_oxdiff_digest_hkl
;
01d21057ccc097e79e3d50be205f5a44dff429
;
_reflns_odcompleteness_completeness 100.00
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C5(H5A), C7(H7), C6(H6A)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 N5(H5), N1(H1)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6)
;
_shelx_res_checksum              53202
_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 1.935
_oxdiff_exptl_absorpt_empirical_full_min 0.322