data_RBH
# 
_chem_comp.id                                    RBH 
_chem_comp.name                                  "~{N}-[(2~{S},3~{S},4~{S},5~{R})-2-(hydroxymethyl)-4,5,6-tris(oxidanyl)oxan-3-yl]-2-oxidanyl-ethanamide" 
_chem_comp.type                                  non-polymer 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H27 N4 O9" 
_chem_comp.mon_nstd_parent_comp_id               GDA 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2022-11-28 
_chem_comp.pdbx_modified_date                    2024-01-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        395.386 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     RBH 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   Y 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        8BQA 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBE 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.pdbx_backbone_atom_flag 
_chem_comp_atom.pdbx_n_terminal_atom_flag 
_chem_comp_atom.pdbx_c_terminal_atom_flag 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
RBH C3  C1  C 0 1 N N S N N N -2.480 1.400  32.429 -4.553 0.916  0.103  C14 RBH 1  
RBH C2  C2  C 0 1 N N R N N N -2.042 1.485  30.967 -5.667 0.529  1.081  C13 RBH 2  
RBH C6  C3  C 0 1 N N N N N N -4.914 -1.531 31.800 -3.570 -2.699 -0.780 C11 RBH 3  
RBH C7  C4  C 0 1 N N N N N N -5.762 0.966  35.783 -0.424 1.015  -1.737 C7  RBH 4  
RBH O2  O1  O 0 1 N N N N N N -0.823 2.201  30.814 -6.570 1.626  1.234  O8  RBH 5  
RBH O8  O2  O 0 1 N N N N N N -4.790 0.286  36.538 0.668  1.668  -1.088 O2  RBH 6  
RBH O4  O3  O 0 1 N N N N N N -6.095 1.733  33.569 -1.313 0.955  0.449  O4  RBH 7  
RBH O6  O4  O 0 1 N N N N N N -4.708 -2.910 31.726 -4.321 -3.767 -1.360 O5  RBH 8  
RBH O5  O5  O 0 1 N N N N N N -3.130 -0.603 30.514 -5.505 -1.760 0.322  O6  RBH 9  
RBH C5  C5  C 0 1 N N S N N N -3.592 -0.787 31.877 -4.469 -1.472 -0.619 C10 RBH 10 
RBH C4  C6  C 0 1 N N S N N N -3.765 0.586  32.543 -3.636 -0.292 -0.113 C9  RBH 11 
RBH C8  C7  C 0 1 N N N N N N -5.378 1.072  34.330 -1.480 0.670  -0.718 C8  RBH 12 
RBH C1  C8  C 0 1 N N R N N N -1.907 0.111  30.374 -6.422 -0.683 0.528  C12 RBH 13 
RBH N4  N1  N 0 1 N N N N N N -4.265 0.457  33.913 -2.610 0.044  -1.103 N4  RBH 14 
RBH O3  O6  O 0 1 N N N N N N -2.703 2.695  32.963 -3.797 2.000  0.645  O9  RBH 15 
RBH H3  H1  H 0 1 N N N N N N -1.691 0.889  33.000 -4.990 1.216  -0.850 H26 RBH 16 
RBH H2  H2  H 0 1 N N N N N N -2.834 2.012  30.415 -5.231 0.277  2.047  H24 RBH 17 
RBH H62 H3  H 0 1 N N N N N N -5.461 -1.200 30.905 -3.196 -3.007 0.197  H20 RBH 18 
RBH H61 H4  H 0 1 N N N N N N -5.508 -1.304 32.698 -2.729 -2.452 -1.428 H19 RBH 19 
RBH H15 H5  H 0 1 N N N N N N -5.884 1.980  36.193 -0.849 1.679  -2.489 H15 RBH 20 
RBH H14 H6  H 0 1 N N N N N N -6.715 0.422  35.859 -0.070 0.102  -2.216 H14 RBH 21 
RBH HO2 H7  H 0 1 N Y N N N N -0.915 3.068  31.191 -7.302 1.450  1.841  H25 RBH 22 
RBH HO6 H9  H 0 1 N N N N N N -5.547 -3.354 31.679 -3.813 -4.580 -1.491 H21 RBH 23 
RBH H5  H10 H 0 1 N N N N N N -2.868 -1.382 32.452 -4.912 -1.218 -1.582 H18 RBH 24 
RBH H4  H11 H 0 1 N N N N N N -4.531 1.122  31.963 -3.159 -0.560 0.830  H17 RBH 25 
RBH H1  H12 H 0 1 N N N N N N -1.118 -0.420 30.927 -6.891 -0.419 -0.419 H2  RBH 26 
RBH H8  H14 H 0 1 N N N N N N -3.757 -0.111 34.560 -2.743 -0.184 -2.036 H16 RBH 27 
RBH HO3 H15 H 0 1 N Y N N N N -2.974 2.621  33.871 -4.316 2.800  0.807  H27 RBH 28 
RBH O1  O7  O 0 1 N Y N N N N -1.591 0.158  29.048 -7.426 -1.085 1.462  O1  RBH 29 
RBH HO1 H28 H 0 1 N Y N N N N -0.776 0.632  28.933 -7.944 -1.850 1.177  H3  RBH 30 
RBH C9  C9  C 0 1 N N N N N N ?      ?      ?      1.730  2.040  -1.970 C1  RBH 31 
RBH C10 C10 C 0 1 N N N N N N ?      ?      ?      2.839  2.727  -1.171 C2  RBH 32 
RBH O9  O8  O 0 1 N N N N N N ?      ?      ?      3.417  1.793  -0.257 O3  RBH 33 
RBH C11 C11 C 0 1 N N N N N N ?      ?      ?      4.469  2.337  0.542  C4  RBH 34 
RBH C12 C12 C 0 1 N N N N N N ?      ?      ?      5.010  1.255  1.478  C5  RBH 35 
RBH O7  O9  O 0 1 N N N N N N ?      ?      ?      5.619  0.218  0.706  O7  RBH 36 
RBH C15 C15 C 0 1 N N N N N N ?      ?      ?      6.160  -0.849 1.489  C15 RBH 37 
RBH C16 C16 C 0 1 N N N N N N ?      ?      ?      6.783  -1.896 0.563  C16 RBH 38 
RBH N3  N3  N 0 1 N N N N N N ?      ?      ?      7.928  -1.309 -0.137 N3  RBH 39 
RBH N2  N2  N 1 1 N N N N N N ?      ?      ?      8.952  -1.755 -0.011 N2  RBH 40 
RBH N1  N4  N 0 1 N N N N N N ?      ?      ?      9.976  -2.201 0.114  N1  RBH 41 
RBH H16 H29 H 0 1 N N N N N N ?      ?      ?      2.129  1.149  -2.454 H1  RBH 42 
RBH H17 H16 H 0 1 N N N N N N ?      ?      ?      1.349  2.725  -2.727 H4  RBH 43 
RBH H18 H17 H 0 1 N N N N N N ?      ?      ?      3.607  3.090  -1.854 H5  RBH 44 
RBH H6  H18 H 0 1 N N N N N N ?      ?      ?      2.421  3.567  -0.616 H6  RBH 45 
RBH H7  H19 H 0 1 N N N N N N ?      ?      ?      5.271  2.691  -0.105 H7  RBH 46 
RBH H19 H8  H 0 1 N N N N N N ?      ?      ?      4.084  3.169  1.133  H8  RBH 47 
RBH H9  H21 H 0 1 N N N N N N ?      ?      ?      5.751  1.691  2.149  H9  RBH 48 
RBH H10 H22 H 0 1 N N N N N N ?      ?      ?      4.191  0.838  2.064  H10 RBH 49 
RBH H11 H23 H 0 1 N N N N N N ?      ?      ?      6.924  -0.456 2.159  H11 RBH 50 
RBH H12 H24 H 0 1 N N N N N N ?      ?      ?      5.364  -1.309 2.074  H12 RBH 51 
RBH H13 H13 H 0 1 N N N N N N ?      ?      ?      7.115  -2.750 1.152  H13 RBH 52 
RBH H22 H26 H 0 1 N N N N N N ?      ?      ?      6.041  -2.224 -0.166 H22 RBH 53 
RBH H23 H27 H 0 1 N N N N N N ?      ?      ?      10.559 -1.887 0.824  H23 RBH 54 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
RBH C1  O5  SING N N 1  
RBH C1  C2  SING N N 2  
RBH O5  C5  SING N N 3  
RBH O2  C2  SING N N 4  
RBH C2  C3  SING N N 5  
RBH O6  C6  SING N N 6  
RBH C6  C5  SING N N 7  
RBH C5  C4  SING N N 8  
RBH C3  C4  SING N N 9  
RBH C3  O3  SING N N 10 
RBH C4  N4  SING N N 11 
RBH O4  C8  DOUB N N 12 
RBH N4  C8  SING N N 13 
RBH C8  C7  SING N N 14 
RBH C7  O8  SING N N 15 
RBH C3  H3  SING N N 16 
RBH C2  H2  SING N N 17 
RBH C6  H62 SING N N 18 
RBH C6  H61 SING N N 19 
RBH C7  H15 SING N N 20 
RBH C7  H14 SING N N 21 
RBH O2  HO2 SING N N 22 
RBH O6  HO6 SING N N 23 
RBH C5  H5  SING N N 24 
RBH C4  H4  SING N N 25 
RBH C1  H1  SING N N 26 
RBH N4  H8  SING N N 27 
RBH O3  HO3 SING N N 28 
RBH C1  O1  SING N N 29 
RBH O1  HO1 SING N N 30 
RBH O8  C9  SING N N 31 
RBH C9  C10 SING N N 32 
RBH C10 O9  SING N N 33 
RBH O9  C11 SING N N 34 
RBH C11 C12 SING N N 35 
RBH C12 O7  SING N N 36 
RBH O7  C15 SING N N 37 
RBH C15 C16 SING N N 38 
RBH C16 N3  SING N N 39 
RBH N3  N2  DOUB N N 40 
RBH N2  N1  DOUB N N 41 
RBH C9  H16 SING N N 42 
RBH C9  H17 SING N N 43 
RBH C10 H18 SING N N 44 
RBH C10 H6  SING N N 45 
RBH C11 H7  SING N N 46 
RBH C11 H19 SING N N 47 
RBH C12 H9  SING N N 48 
RBH C12 H10 SING N N 49 
RBH C15 H11 SING N N 50 
RBH C15 H12 SING N N 51 
RBH C16 H13 SING N N 52 
RBH C16 H22 SING N N 53 
RBH N1  H23 SING N N 54 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
RBH InChI            InChI                1.06    "InChI=1S/C14H26N4O9/c15-18-16-1-2-24-3-4-25-5-6-26-8-10(20)17-11-9(7-19)27-14(23)13(22)12(11)21/h9,11-15,19,21-23H,1-8H2/p+1/t9-,11-,12+,13-,14-/m1/s1" 
RBH InChIKey         InChI                1.06    RPRHCZBAXXPRCX-RGCYKPLRSA-O                                                                                                                              
RBH SMILES_CANONICAL CACTVS               3.385   "OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1NC(=O)COCCOCCOCCN=[N+]=N"                                                                                     
RBH SMILES           CACTVS               3.385   "OC[CH]1O[CH](O)[CH](O)[CH](O)[CH]1NC(=O)COCCOCCOCCN=[N+]=N"                                                                                             
RBH SMILES_CANONICAL "OpenEye OEToolkits" 3.1.0.0 "C(COCCOCCOCC(=O)N[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)O)CO)N=[N+]=N"                                                                                    
RBH SMILES           "OpenEye OEToolkits" 3.1.0.0 "C(COCCOCCOCC(=O)NC1C(OC(C(C1O)O)O)CO)N=[N+]=N"                                                                                                          
# 
_pdbx_chem_comp_identifier.comp_id           RBH 
_pdbx_chem_comp_identifier.type              "SYSTEMATIC NAME" 
_pdbx_chem_comp_identifier.program           "OpenEye OEToolkits" 
_pdbx_chem_comp_identifier.program_version   3.1.0.0 
_pdbx_chem_comp_identifier.identifier        "azanylidene-[2-[2-[2-[2-[[(2~{S},3~{S},4~{S},5~{R},6~{R})-2-(hydroxymethyl)-4,5,6-tris(oxidanyl)oxan-3-yl]amino]-2-oxidanylidene-ethoxy]ethoxy]ethoxy]ethylimino]azanium" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
RBH "Create component"         2022-11-28 PDBE 
RBH "Initial release"          2023-11-29 RCSB 
RBH "Modify leaving atom flag" 2024-01-14 PDBE 
# 
