data_G20
# 
_chem_comp.id                                    G20 
_chem_comp.name                                  "4-ACETYL-4-GUANIDINO-6-METHYL(PROPYL)CARBOXAMIDE-4,5-DIHYDRO-2H-PYRAN-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H23 N5 O5" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_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                        341.363 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     G20 
_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        2QWF 
_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 
G20 C1   C1   C 0 1 N N N 23.631 19.829 64.890 3.269  0.120  -2.195 C1   G20 1  
G20 O1A  O1A  O 0 1 N N N 24.220 20.893 65.141 3.392  -0.136 -3.376 O1A  G20 2  
G20 O1B  O1B  O 0 1 N N N 22.404 19.670 65.115 4.350  0.449  -1.460 O1B  G20 3  
G20 C2   C2   C 0 1 N N N 24.430 18.879 64.220 1.937  0.072  -1.565 C2   G20 4  
G20 C3   C3   C 0 1 N N N 23.967 17.697 63.926 0.924  -0.256 -2.344 C3   G20 5  
G20 C4   C4   C 0 1 N N S 24.592 16.730 62.821 -0.487 -0.361 -1.826 C4   G20 6  
G20 C5   C5   C 0 1 N N R 25.983 16.876 62.786 -0.528 0.255  -0.420 C5   G20 7  
G20 N5   N5   N 0 1 N N N 26.592 16.177 61.679 -1.735 -0.188 0.282  N5   G20 8  
G20 C10  C10  C 0 1 N N N 27.077 14.949 61.837 -2.468 0.696  0.986  C10  G20 9  
G20 O10  O10  O 0 1 N N N 27.057 14.354 62.916 -2.169 1.872  0.981  O10  G20 10 
G20 C11  C11  C 0 1 N N N 27.570 14.290 60.559 -3.659 0.225  1.780  C11  G20 11 
G20 C6   C6   C 0 1 N N R 26.277 18.367 62.827 0.721  -0.225 0.327  C6   G20 12 
G20 O6   O6   O 0 1 N N N 25.739 18.935 63.984 1.875  0.367  -0.255 O6   G20 13 
G20 C7   C7   C 0 1 N N N 27.781 18.403 62.922 0.626  0.176  1.777  C7   G20 14 
G20 O7   O7   O 0 1 N N N 28.329 18.056 63.976 1.175  1.187  2.162  O7   G20 15 
G20 N8   N8   N 0 1 N N N 28.479 18.732 61.821 -0.068 -0.586 2.644  N8   G20 16 
G20 C81  C81  C 0 1 N N N 27.982 19.086 60.480 -0.625 -1.868 2.207  C81  G20 17 
G20 C9   C9   C 0 1 N N N 29.952 18.690 62.006 -0.266 -0.132 4.023  C9   G20 18 
G20 C91  C91  C 0 1 N N N 30.449 17.288 62.443 0.884  -0.637 4.896  C91  G20 19 
G20 C92  C92  C 0 1 N N N 31.945 17.121 62.324 0.677  -0.164 6.336  C92  G20 20 
G20 NE   NE   N 0 1 N N N 24.236 15.291 62.936 -1.395 0.369  -2.714 NE   G20 21 
G20 CZ   CZ   C 0 1 N N N 23.862 14.335 61.987 -1.984 -0.275 -3.776 CZ   G20 22 
G20 NH1  NH1  N 0 1 N N N 23.842 14.659 60.699 -1.736 -1.536 -3.992 NH1  G20 23 
G20 NH2  NH2  N 0 1 N N N 23.618 13.070 62.357 -2.836 0.409  -4.610 NH2  G20 24 
G20 HO1  HO1  H 0 1 N N N 21.953 18.856 64.923 5.224  0.480  -1.873 HO1  G20 25 
G20 H3   H3   H 0 1 N N N 23.093 17.524 64.577 1.112  -0.457 -3.388 H3   G20 26 
G20 H4   H4   H 0 1 N N N 24.125 17.060 61.864 -0.785 -1.408 -1.777 H4   G20 27 
G20 H5   H5   H 0 1 N N N 26.453 16.389 63.672 -0.520 1.342  -0.492 H5   G20 28 
G20 HN5  HN5  H 0 1 N N N 26.683 16.568 60.741 -2.006 -1.118 0.240  HN5  G20 29 
G20 H111 1H11 H 0 0 N N N 27.976 13.260 60.691 -4.160 1.084  2.227  H111 G20 30 
G20 H112 2H11 H 0 0 N N N 26.764 14.291 59.788 -4.352 -0.296 1.121  H112 G20 31 
G20 H113 3H11 H 0 0 N N N 28.321 14.940 60.053 -3.326 -0.450 2.567  H113 G20 32 
G20 H6   H6   H 0 1 N N N 25.854 18.921 61.956 0.794  -1.311 0.255  H6   G20 33 
G20 H811 1H81 H 0 0 N N N 28.560 19.358 59.566 -0.459 -1.991 1.137  H811 G20 34 
G20 H812 2H81 H 0 0 N N N 27.327 18.237 60.173 -0.135 -2.679 2.746  H812 G20 35 
G20 H813 3H81 H 0 0 N N N 27.268 19.927 60.641 -1.695 -1.889 2.414  H813 G20 36 
G20 H91  1H9  H 0 1 N N N 30.483 19.038 61.089 -1.209 -0.524 4.402  H91  G20 37 
G20 H92  2H9  H 0 1 N N N 30.291 19.477 62.718 -0.289 0.957  4.047  H92  G20 38 
G20 H911 1H91 H 0 0 N N N 30.104 17.050 63.476 1.827  -0.245 4.516  H911 G20 39 
G20 H912 2H91 H 0 0 N N N 29.915 16.485 61.882 0.907  -1.727 4.872  H912 G20 40 
G20 H921 1H92 H 0 0 N N N 32.302 16.112 62.638 1.496  -0.524 6.958  H921 G20 41 
G20 H922 2H92 H 0 0 N N N 32.289 17.358 61.290 0.654  0.925  6.360  H922 G20 42 
G20 H923 3H92 H 0 0 N N N 32.479 17.923 62.884 -0.266 -0.556 6.715  H923 G20 43 
G20 HNE  HNE  H 0 1 N N N 23.482 15.271 63.623 -1.580 1.307  -2.554 HNE  G20 44 
G20 HN1  HN1  H 0 1 N N N 24.049 14.796 61.688 -2.151 -1.991 -4.741 HN1  G20 45 
G20 HN21 1HN2 H 0 0 N N N 23.345 12.372 61.664 -3.252 -0.045 -5.359 HN21 G20 46 
G20 HN22 2HN2 H 0 0 N N N 22.912 13.082 63.093 -3.021 1.348  -4.449 HN22 G20 47 
# 
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 
G20 C1  O1A  DOUB N N 1  
G20 C1  O1B  SING N N 2  
G20 C1  C2   SING N N 3  
G20 O1B HO1  SING N N 4  
G20 C2  C3   DOUB N N 5  
G20 C2  O6   SING N N 6  
G20 C3  C4   SING N N 7  
G20 C3  H3   SING N N 8  
G20 C4  C5   SING N N 9  
G20 C4  NE   SING N N 10 
G20 C4  H4   SING N N 11 
G20 C5  N5   SING N N 12 
G20 C5  C6   SING N N 13 
G20 C5  H5   SING N N 14 
G20 N5  C10  SING N N 15 
G20 N5  HN5  SING N N 16 
G20 C10 O10  DOUB N N 17 
G20 C10 C11  SING N N 18 
G20 C11 H111 SING N N 19 
G20 C11 H112 SING N N 20 
G20 C11 H113 SING N N 21 
G20 C6  O6   SING N N 22 
G20 C6  C7   SING N N 23 
G20 C6  H6   SING N N 24 
G20 C7  O7   DOUB N N 25 
G20 C7  N8   SING N N 26 
G20 N8  C81  SING N N 27 
G20 N8  C9   SING N N 28 
G20 C81 H811 SING N N 29 
G20 C81 H812 SING N N 30 
G20 C81 H813 SING N N 31 
G20 C9  C91  SING N N 32 
G20 C9  H91  SING N N 33 
G20 C9  H92  SING N N 34 
G20 C91 C92  SING N N 35 
G20 C91 H911 SING N N 36 
G20 C91 H912 SING N N 37 
G20 C92 H921 SING N N 38 
G20 C92 H922 SING N N 39 
G20 C92 H923 SING N N 40 
G20 NE  CZ   SING N N 41 
G20 NE  HNE  SING N N 42 
G20 CZ  NH1  DOUB N N 43 
G20 CZ  NH2  SING N N 44 
G20 NH1 HN1  SING N N 45 
G20 NH2 HN21 SING N N 46 
G20 NH2 HN22 SING N N 47 
# 
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 
G20 SMILES           ACDLabs              10.04 O=C(O)C=1OC(C(=O)N(CCC)C)C(NC(=O)C)C(NC(=[N@H])N)C=1                                                                                                                                         
G20 InChI            InChI                1.02b InChI=1/C14H23N5O5/c1-4-5-19(3)12(21)11-10(17-7(2)20)8(18-14(15)16)6-9(24-11)13(22)23/h6,8,10-11H,4-5H2,1-3H3,(H,17,20)(H,22,23)(H4,15,16,18)/t8-,10+,11+/m0/s1/f/h15,17-18,22H,16H2/b15-14- 
G20 InChIKey         InChI                1.02b QPJWMZVTNXFTKV-MQLCJMBNDO                                                                                                                                                                    
G20 SMILES_CANONICAL CACTVS               3.341 CCCN(C)C(=O)[C@@H]1OC(=C[C@H](NC(N)=N)[C@H]1NC(C)=O)C(O)=O                                                                                                                                   
G20 SMILES           CACTVS               3.341 CCCN(C)C(=O)[CH]1OC(=C[CH](NC(N)=N)[CH]1NC(C)=O)C(O)=O                                                                                                                                       
G20 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 [H]/N=C(/N)\N[C@H]1C=C(O[C@H]([C@@H]1NC(=O)C)C(=O)N(C)CCC)C(=O)O                                                                                                                             
G20 SMILES           "OpenEye OEToolkits" 1.5.0 [H]N=C(N)NC1C=C(OC(C1NC(=O)C)C(=O)N(C)CCC)C(=O)O                                                                                                                                             
# 
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 
G20 "SYSTEMATIC NAME" ACDLabs              10.04 "(2R,3R,4S)-3-(acetylamino)-4-carbamimidamido-2-[methyl(propyl)carbamoyl]-3,4-dihydro-2H-pyran-6-carboxylic acid (non-preferred name)" 
G20 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(4S,5R,6R)-5-acetamido-4-carbamimidamido-6-(methyl-propyl-carbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid"                          
# 
