data_HRB
# 
_chem_comp.id                                    HRB 
_chem_comp.name                                  N-ACETYL-1-[(2R,3S,5R)-5-HYDROXY-2-PENTYLTETRAHYDROFURAN-3-YL]-L-HISTIDINE 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C17 H27 N3 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-02-06 
_chem_comp.pdbx_modified_date                    2008-10-14 
_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                        353.413 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     HRB 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2DDQ 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
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.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 
HRB CP5  CP5  C 0 1 N N N 46.490 -1.081 5.786  4.200  5.411  0.452  CP5  HRB 1  
HRB CP4  CP4  C 0 1 N N N 47.557 -1.802 4.959  4.247  4.078  -0.299 CP4  HRB 2  
HRB CP3  CP3  C 0 1 N N N 48.332 -0.803 4.101  3.471  3.021  0.490  CP3  HRB 3  
HRB CP2  CP2  C 0 1 N N N 49.471 -1.494 3.347  3.518  1.689  -0.260 CP2  HRB 4  
HRB CP1  CP1  C 0 1 N N N 50.257 -0.479 2.516  2.742  0.632  0.529  CP1  HRB 5  
HRB C5   C5   C 0 1 N N R 51.413 -1.151 1.768  2.788  -0.701 -0.222 C5   HRB 6  
HRB O1   O1   O 0 1 N N N 50.941 -2.124 0.814  4.126  -1.245 -0.209 O1   HRB 7  
HRB C2   C2   C 0 1 N N R 51.233 -1.617 -0.503 4.007  -2.656 -0.453 C2   HRB 8  
HRB O2   O2   O 0 1 N N N 50.196 -0.731 -0.945 5.018  -3.361 0.270  O2   HRB 9  
HRB C3   C3   C 0 1 N N N 52.545 -0.859 -0.290 2.611  -3.090 0.035  C3   HRB 10 
HRB C4   C4   C 0 1 N N S 52.137 -0.075 0.956  1.950  -1.774 0.519  C4   HRB 11 
HRB NE2  NE2  N 0 1 Y N N 53.302 0.492  1.664  0.543  -1.716 0.117  NE2  HRB 12 
HRB CD2  CD2  C 0 1 Y N N 54.295 -0.182 2.227  -0.536 -1.595 0.951  CD2  HRB 13 
HRB CE1  CE1  C 0 1 Y N N 53.549 1.801  1.737  0.067  -1.778 -1.146 CE1  HRB 14 
HRB ND1  ND1  N 0 1 Y N N 54.720 1.929  2.351  -1.235 -1.695 -1.107 ND1  HRB 15 
HRB CG   CG   C 0 1 Y N N 55.185 0.715  2.646  -1.633 -1.578 0.169  CG   HRB 16 
HRB CB   CB   C 0 1 N N N 56.536 0.420  3.305  -3.057 -1.457 0.644  CB   HRB 17 
HRB CA   CA   C 0 1 N N S 57.670 1.177  2.606  -3.732 -0.280 -0.062 CA   HRB 18 
HRB C    C    C 0 1 N N N 58.957 1.075  3.429  -5.189 -0.233 0.320  C    HRB 19 
HRB O    O    O 0 1 N N N 59.181 1.998  4.240  -5.989 -1.277 0.047  O    HRB 20 
HRB OXT  OXT  O 0 1 N N N 59.695 0.083  3.222  -5.638 0.743  0.872  OXT  HRB 21 
HRB N    N    N 0 1 N N N 57.888 0.642  1.255  -3.082 0.970  0.340  N    HRB 22 
HRB CA1  CA1  C 0 1 N N N 57.988 1.430  0.183  -3.127 2.045  -0.471 CA1  HRB 23 
HRB CA2  CA2  C 0 1 N N N 58.226 0.694  -1.136 -2.458 3.330  -0.057 CA2  HRB 24 
HRB OA1  OA1  O 0 1 N N N 57.903 2.656  0.214  -3.706 1.978  -1.535 OA1  HRB 25 
HRB HP51 1HP5 H 0 0 N N N 45.582 -1.701 5.833  4.753  6.164  -0.110 HP51 HRB 26 
HRB HP52 2HP5 H 0 0 N N N 46.251 -0.116 5.315  3.164  5.729  0.563  HP52 HRB 27 
HRB HP53 3HP5 H 0 0 N N N 46.869 -0.908 6.804  4.651  5.289  1.437  HP53 HRB 28 
HRB HP41 1HP4 H 0 0 N N N 47.065 -2.532 4.300  3.796  4.200  -1.284 HP41 HRB 29 
HRB HP42 2HP4 H 0 0 N N N 48.256 -2.313 5.638  5.284  3.760  -0.410 HP42 HRB 30 
HRB HP31 1HP3 H 0 0 N N N 48.763 -0.034 4.760  3.922  2.900  1.475  HP31 HRB 31 
HRB HP32 2HP3 H 0 0 N N N 47.644 -0.349 3.372  2.434  3.340  0.601  HP32 HRB 32 
HRB HP21 1HP2 H 0 0 N N N 49.044 -2.252 2.673  3.067  1.810  -1.245 HP21 HRB 33 
HRB HP22 2HP2 H 0 0 N N N 50.149 -1.967 4.073  4.554  1.371  -0.371 HP22 HRB 34 
HRB HP11 1HP1 H 0 0 N N N 50.674 0.279  3.195  3.192  0.510  1.514  HP11 HRB 35 
HRB HP12 2HP1 H 0 0 N N N 49.579 -0.017 1.783  1.705  0.950  0.640  HP12 HRB 36 
HRB H5   H5   H 0 1 N N N 52.056 -1.644 2.512  2.434  -0.576 -1.245 H5   HRB 37 
HRB H2   H2   H 0 1 N N N 51.304 -2.402 -1.271 4.105  -2.858 -1.519 H2   HRB 38 
HRB HO2  HO2  H 0 1 N N N 49.616 -0.535 -0.219 5.870  -3.048 -0.064 HO2  HRB 39 
HRB H31  1H3  H 0 1 N N N 52.894 -0.257 -1.142 2.037  -3.522 -0.785 H31  HRB 40 
HRB H32  2H3  H 0 1 N N N 53.411 -1.518 -0.130 2.697  -3.800 0.857  H32  HRB 41 
HRB H4   H4   H 0 1 N N N 51.517 0.810  0.749  2.049  -1.663 1.599  H4   HRB 42 
HRB HD2  HD2  H 0 1 N N N 54.368 -1.255 2.327  -0.512 -1.521 2.028  HD2  HRB 43 
HRB HE1  HE1  H 0 1 N N N 52.921 2.599  1.369  0.665  -1.879 -2.039 HE1  HRB 44 
HRB HB1  1HB  H 0 1 N N N 56.735 -0.659 3.226  -3.597 -2.376 0.415  HB1  HRB 45 
HRB HB2  2HB  H 0 1 N N N 56.495 0.733  4.359  -3.068 -1.289 1.721  HB2  HRB 46 
HRB HA   HA   H 0 1 N N N 57.385 2.236  2.521  -3.644 -0.404 -1.141 HA   HRB 47 
HRB HO   HO   H 0 1 N N N 60.005 1.837  4.684  -6.924 -1.247 0.292  HO   HRB 48 
HRB HN   HN   H 0 1 N N N 57.964 -0.348 1.135  -2.618 1.023  1.191  HN   HRB 49 
HRB HA21 1HA2 H 0 0 N N N 57.396 -0.003 -1.322 -1.427 3.333  -0.412 HA21 HRB 50 
HRB HA22 2HA2 H 0 0 N N N 59.170 0.133  -1.077 -2.994 4.174  -0.490 HA22 HRB 51 
HRB HA23 3HA2 H 0 0 N N N 58.283 1.423  -1.958 -2.468 3.411  1.030  HA23 HRB 52 
# 
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 
HRB CP5 CP4  SING N N 1  
HRB CP5 HP51 SING N N 2  
HRB CP5 HP52 SING N N 3  
HRB CP5 HP53 SING N N 4  
HRB CP4 CP3  SING N N 5  
HRB CP4 HP41 SING N N 6  
HRB CP4 HP42 SING N N 7  
HRB CP3 CP2  SING N N 8  
HRB CP3 HP31 SING N N 9  
HRB CP3 HP32 SING N N 10 
HRB CP2 CP1  SING N N 11 
HRB CP2 HP21 SING N N 12 
HRB CP2 HP22 SING N N 13 
HRB CP1 C5   SING N N 14 
HRB CP1 HP11 SING N N 15 
HRB CP1 HP12 SING N N 16 
HRB C5  O1   SING N N 17 
HRB C5  C4   SING N N 18 
HRB C5  H5   SING N N 19 
HRB O1  C2   SING N N 20 
HRB C2  O2   SING N N 21 
HRB C2  C3   SING N N 22 
HRB C2  H2   SING N N 23 
HRB O2  HO2  SING N N 24 
HRB C3  C4   SING N N 25 
HRB C3  H31  SING N N 26 
HRB C3  H32  SING N N 27 
HRB C4  NE2  SING N N 28 
HRB C4  H4   SING N N 29 
HRB NE2 CD2  SING Y N 30 
HRB NE2 CE1  SING Y N 31 
HRB CD2 CG   DOUB Y N 32 
HRB CD2 HD2  SING N N 33 
HRB CE1 ND1  DOUB Y N 34 
HRB CE1 HE1  SING N N 35 
HRB ND1 CG   SING Y N 36 
HRB CG  CB   SING N N 37 
HRB CB  CA   SING N N 38 
HRB CB  HB1  SING N N 39 
HRB CB  HB2  SING N N 40 
HRB CA  C    SING N N 41 
HRB CA  N    SING N N 42 
HRB CA  HA   SING N N 43 
HRB C   O    SING N N 44 
HRB C   OXT  DOUB N N 45 
HRB O   HO   SING N N 46 
HRB N   CA1  SING N N 47 
HRB N   HN   SING N N 48 
HRB CA1 CA2  SING N N 49 
HRB CA1 OA1  DOUB N N 50 
HRB CA2 HA21 SING N N 51 
HRB CA2 HA22 SING N N 52 
HRB CA2 HA23 SING N N 53 
# 
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 
HRB SMILES           ACDLabs              10.04 O=C(O)C(NC(=O)C)Cc1ncn(c1)C2C(OC(O)C2)CCCCC                                                                                                                                 
HRB InChI            InChI                1.02b InChI=1/C17H27N3O5/c1-3-4-5-6-15-14(8-16(22)25-15)20-9-12(18-10-20)7-13(17(23)24)19-11(2)21/h9-10,13-16,22H,3-8H2,1-2H3,(H,19,21)(H,23,24)/t13-,14-,15+,16+/m0/s1/f/h19,23H 
HRB InChIKey         InChI                1.02b INPAKWNFLOQYEI-ZEHCTYQSDC                                                                                                                                                   
HRB SMILES_CANONICAL CACTVS               3.341 CCCCC[C@H]1O[C@@H](O)C[C@@H]1n2cnc(C[C@H](NC(C)=O)C(O)=O)c2                                                                                                                 
HRB SMILES           CACTVS               3.341 CCCCC[CH]1O[CH](O)C[CH]1n2cnc(C[CH](NC(C)=O)C(O)=O)c2                                                                                                                       
HRB SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCC[C@@H]1[C@H](C[C@@H](O1)O)n2cc(nc2)C[C@@H](C(=O)O)NC(=O)C                                                                                                              
HRB SMILES           "OpenEye OEToolkits" 1.5.0 CCCCCC1C(CC(O1)O)n2cc(nc2)CC(C(=O)O)NC(=O)C                                                                                                                                 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
HRB "SYSTEMATIC NAME" ACDLabs              10.04 N-acetyl-1-[(2R,3S,5R)-5-hydroxy-2-pentyltetrahydrofuran-3-yl]-L-histidine                      
HRB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-acetamido-3-[1-[(2R,3S,5R)-5-hydroxy-2-pentyl-oxolan-3-yl]imidazol-4-yl]propanoic acid" 
# 
