data_HAG
# 
_chem_comp.id                                    HAG 
_chem_comp.name                                  4-S-GLUTATHIONYL-5-PENTYL-TETRAHYDRO-FURAN-2-OL 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C19 H33 N3 O8 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         GSHNA 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-27 
_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                        463.546 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     HAG 
_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        1B48 
_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 
HAG C1   C1   C 0 1 N N N 34.358 16.888 30.163 -4.369 0.395  -5.441 C1   HAG 1  
HAG C2   C2   C 0 1 N N N 32.489 17.479 36.098 2.663  0.851  -1.785 C2   HAG 2  
HAG C3   C3   C 0 1 N N N 35.257 17.588 38.329 4.071  -1.972 -3.713 C3   HAG 3  
HAG N1   N1   N 0 1 N N N 35.146 19.051 29.072 -3.007 -1.567 -4.996 N1   HAG 4  
HAG CA1  CA1  C 0 1 N N S 35.205 18.142 30.325 -3.569 -0.347 -4.402 CA1  HAG 5  
HAG O11  O11  O 0 1 N N N 33.892 16.093 31.061 -5.420 1.142  -5.071 O11  HAG 6  
HAG O12  O12  O 0 1 N N N 33.966 16.404 28.898 -4.064 0.317  -6.608 O12  HAG 7  
HAG CB1  CB1  C 0 1 N N N 34.733 19.124 31.463 -2.432 0.545  -3.901 CB1  HAG 8  
HAG CG1  CG1  C 0 1 N N N 35.160 18.489 32.770 -1.619 -0.208 -2.846 CG1  HAG 9  
HAG CD1  CD1  C 0 1 N N N 34.430 19.024 33.962 -0.499 0.670  -2.352 CD1  HAG 10 
HAG OE1  OE1  O 0 1 N N N 34.914 19.752 34.883 -0.364 1.789  -2.799 OE1  HAG 11 
HAG N2   N2   N 0 1 N N N 33.103 18.670 34.045 0.351  0.213  -1.412 N2   HAG 12 
HAG CA2  CA2  C 0 1 N N R 32.473 18.882 35.386 1.440  1.068  -0.932 CA2  HAG 13 
HAG O2   O2   O 0 1 N N N 32.034 16.620 35.344 3.453  1.755  -1.954 O2   HAG 14 
HAG CB2  CB2  C 0 1 N N N 31.020 19.406 35.206 1.763  0.714  0.520  CB2  HAG 15 
HAG SG2  SG2  S 0 1 N N N 30.801 20.570 36.534 0.291  0.975  1.548  SG2  HAG 16 
HAG N3   N3   N 0 1 N N N 32.995 17.515 37.346 2.878  -0.348 -2.362 N3   HAG 17 
HAG CA3  CA3  C 0 1 N N N 34.108 18.410 37.754 4.067  -0.559 -3.192 CA3  HAG 18 
HAG O31  O31  O 0 1 N N N 35.268 17.258 39.573 5.072  -2.394 -4.502 O31  HAG 19 
HAG O32  O32  O 0 1 N N N 36.217 17.257 37.451 3.173  -2.727 -3.422 O32  HAG 20 
HAG C41  C41  C 0 1 N N S 31.253 22.301 36.208 0.948  0.491  3.168  C41  HAG 21 
HAG C42  C42  C 0 1 N N N 32.653 22.586 35.773 2.127  1.414  3.585  C42  HAG 22 
HAG O42  O42  O 0 1 N N N 33.504 23.586 33.581 2.685  0.158  5.609  O42  HAG 23 
HAG C43  C43  C 0 1 N N R 32.590 22.593 34.223 2.032  1.335  5.129  C43  HAG 24 
HAG O43  O43  O 0 1 N N N 31.237 22.917 33.902 0.626  1.277  5.416  O43  HAG 25 
HAG C44  C44  C 0 1 N N R 30.320 22.781 35.055 -0.082 0.753  4.287  C44  HAG 26 
HAG C45  C45  C 0 1 N N N 29.738 24.187 35.414 -0.775 -0.555 4.671  C45  HAG 27 
HAG C46  C46  C 0 1 N N N 28.769 24.763 34.305 -1.791 -0.287 5.784  C46  HAG 28 
HAG C47  C47  C 0 1 N N N 27.867 23.898 33.366 -2.484 -1.596 6.168  C47  HAG 29 
HAG C48  C48  C 0 1 N N N 27.081 22.749 34.002 -3.499 -1.328 7.280  C48  HAG 30 
HAG C49  C49  C 0 1 N N N 26.551 22.847 35.407 -4.193 -2.637 7.664  C49  HAG 31 
HAG HN11 1HN1 H 0 0 N N N 35.713 19.891 29.180 -2.418 -1.274 -5.760 HN11 HAG 32 
HAG HN12 2HN1 H 0 0 N N N 34.183 19.284 28.829 -2.400 -1.975 -4.301 HN12 HAG 33 
HAG HCA1 HCA1 H 0 0 N N N 36.209 17.708 30.541 -4.216 -0.614 -3.567 HCA1 HAG 34 
HAG HO11 HO11 H 0 0 N N N 33.363 15.310 30.959 -5.934 1.619  -5.738 HO11 HAG 35 
HAG HB11 1HB1 H 0 0 N N N 35.106 20.166 31.333 -2.848 1.451  -3.460 HB11 HAG 36 
HAG HB12 2HB1 H 0 0 N N N 33.644 19.363 31.420 -1.784 0.812  -4.736 HB12 HAG 37 
HAG HG12 2HG1 H 0 0 N N N 35.068 17.379 32.717 -1.203 -1.114 -3.286 HG12 HAG 38 
HAG HG11 1HG1 H 0 0 N N N 36.262 18.578 32.910 -2.267 -0.475 -2.011 HG11 HAG 39 
HAG HN21 1HN2 H 0 0 N N N 32.643 18.296 33.214 0.243  -0.681 -1.054 HN21 HAG 40 
HAG HCA2 HCA2 H 0 0 N N N 33.020 19.639 35.994 1.135  2.112  -0.992 HCA2 HAG 41 
HAG HB21 1HB2 H 0 0 N N N 30.808 19.824 34.194 2.573  1.350  0.878  HB21 HAG 42 
HAG HB22 2HB2 H 0 0 N N N 30.247 18.603 35.171 2.067  -0.330 0.581  HB22 HAG 43 
HAG HN31 1HN3 H 0 0 N N N 32.535 16.864 37.982 2.246  -1.071 -2.227 HN31 HAG 44 
HAG HA31 1HA3 H 0 0 N N N 33.768 19.203 38.459 4.053  0.137  -4.030 HA31 HAG 45 
HAG HA32 2HA3 H 0 0 N N N 34.442 19.067 36.918 4.962  -0.389 -2.594 HA32 HAG 46 
HAG HO31 HO31 H 0 0 N N N 35.983 16.746 39.931 5.075  -3.301 -4.836 HO31 HAG 47 
HAG HC41 HC41 H 0 0 N N N 31.149 22.822 37.188 1.257  -0.553 3.163  HC41 HAG 48 
HAG H421 1H42 H 0 0 N N N 33.084 23.514 36.213 1.969  2.434  3.233  H421 HAG 49 
HAG H422 2H42 H 0 0 N N N 33.410 21.883 36.193 3.079  1.021  3.229  H422 HAG 50 
HAG HO42 HO42 H 0 0 N N N 33.465 23.590 32.631 2.557  0.138  6.567  HO42 HAG 51 
HAG HC43 HC43 H 0 0 N N N 32.920 21.600 33.837 2.474  2.223  5.582  HC43 HAG 52 
HAG HC44 HC44 H 0 0 N N N 29.465 22.090 34.863 -0.822 1.477  3.946  HC44 HAG 53 
HAG H451 1H45 H 0 0 N N N 29.234 24.165 36.408 -0.031 -1.270 5.023  H451 HAG 54 
HAG H452 2H45 H 0 0 N N N 30.557 24.909 35.638 -1.289 -0.963 3.801  H452 HAG 55 
HAG H461 1H46 H 0 0 N N N 28.096 25.492 34.813 -2.534 0.427  5.432  H461 HAG 56 
HAG H462 2H46 H 0 0 N N N 29.387 25.414 33.644 -1.277 0.120  6.654  H462 HAG 57 
HAG H471 1H47 H 0 0 N N N 27.163 24.564 32.814 -1.740 -2.311 6.519  H471 HAG 58 
HAG H472 2H47 H 0 0 N N N 28.483 23.502 32.525 -2.997 -2.004 5.297  H472 HAG 59 
HAG H481 1H48 H 0 0 N N N 26.227 22.501 33.328 -4.243 -0.612 6.928  H481 HAG 60 
HAG H482 2H48 H 0 0 N N N 27.703 21.826 33.932 -2.986 -0.920 8.150  H482 HAG 61 
HAG H491 1H49 H 0 0 N N N 25.978 22.009 35.870 -4.916 -2.446 8.456  H491 HAG 62 
HAG H492 2H49 H 0 0 N N N 27.404 23.094 36.080 -4.706 -3.045 6.793  H492 HAG 63 
HAG H493 3H49 H 0 0 N N N 25.928 23.769 35.476 -3.449 -3.352 8.015  H493 HAG 64 
# 
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 
HAG C1  CA1  SING N N 1  
HAG C1  O11  SING N N 2  
HAG C1  O12  DOUB N N 3  
HAG C2  CA2  SING N N 4  
HAG C2  O2   DOUB N N 5  
HAG C2  N3   SING N N 6  
HAG C3  CA3  SING N N 7  
HAG C3  O31  SING N N 8  
HAG C3  O32  DOUB N N 9  
HAG N1  CA1  SING N N 10 
HAG N1  HN11 SING N N 11 
HAG N1  HN12 SING N N 12 
HAG CA1 CB1  SING N N 13 
HAG CA1 HCA1 SING N N 14 
HAG O11 HO11 SING N N 15 
HAG CB1 CG1  SING N N 16 
HAG CB1 HB11 SING N N 17 
HAG CB1 HB12 SING N N 18 
HAG CG1 CD1  SING N N 19 
HAG CG1 HG12 SING N N 20 
HAG CG1 HG11 SING N N 21 
HAG CD1 OE1  DOUB N N 22 
HAG CD1 N2   SING N N 23 
HAG N2  CA2  SING N N 24 
HAG N2  HN21 SING N N 25 
HAG CA2 CB2  SING N N 26 
HAG CA2 HCA2 SING N N 27 
HAG CB2 SG2  SING N N 28 
HAG CB2 HB21 SING N N 29 
HAG CB2 HB22 SING N N 30 
HAG SG2 C41  SING N N 31 
HAG N3  CA3  SING N N 32 
HAG N3  HN31 SING N N 33 
HAG CA3 HA31 SING N N 34 
HAG CA3 HA32 SING N N 35 
HAG O31 HO31 SING N N 36 
HAG C41 C42  SING N N 37 
HAG C41 C44  SING N N 38 
HAG C41 HC41 SING N N 39 
HAG C42 C43  SING N N 40 
HAG C42 H421 SING N N 41 
HAG C42 H422 SING N N 42 
HAG O42 C43  SING N N 43 
HAG O42 HO42 SING N N 44 
HAG C43 O43  SING N N 45 
HAG C43 HC43 SING N N 46 
HAG O43 C44  SING N N 47 
HAG C44 C45  SING N N 48 
HAG C44 HC44 SING N N 49 
HAG C45 C46  SING N N 50 
HAG C45 H451 SING N N 51 
HAG C45 H452 SING N N 52 
HAG C46 C47  SING N N 53 
HAG C46 H461 SING N N 54 
HAG C46 H462 SING N N 55 
HAG C47 C48  SING N N 56 
HAG C47 H471 SING N N 57 
HAG C47 H472 SING N N 58 
HAG C48 C49  SING N N 59 
HAG C48 H481 SING N N 60 
HAG C48 H482 SING N N 61 
HAG C49 H491 SING N N 62 
HAG C49 H492 SING N N 63 
HAG C49 H493 SING N N 64 
# 
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 
HAG SMILES           ACDLabs              10.04 O=C(O)C(N)CCC(=O)NC(C(=O)NCC(=O)O)CSC1C(OC(O)C1)CCCCC 
HAG InChI            InChI                1.02b 
InChI=1/C19H33N3O8S/c1-2-3-4-5-13-14(8-17(26)30-13)31-10-12(18(27)21-9-16(24)25)22-15(23)7-6-11(20)19(28)29/h11-14,17,26H,2-10,20H2,1H3,(H,21,27)(H,22,23)(H,24,25)(H,28,29)/t11-,12-,13+,14-,17+/m0/s1/f/h21-22,24,28H 
HAG InChIKey         InChI                1.02b ICRIFHIWWXQBPY-BJFGAEPWDE 
HAG SMILES_CANONICAL CACTVS               3.341 CCCCC[C@H]1O[C@@H](O)C[C@@H]1SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O 
HAG SMILES           CACTVS               3.341 CCCCC[CH]1O[CH](O)C[CH]1SC[CH](NC(=O)CC[CH](N)C(O)=O)C(=O)NCC(O)=O 
HAG SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CCCCC[C@@H]1[C@H](C[C@@H](O1)O)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N 
HAG SMILES           "OpenEye OEToolkits" 1.5.0 CCCCCC1C(CC(O1)O)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N 
# 
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 
HAG "SYSTEMATIC NAME" ACDLabs              10.04 L-gamma-glutamyl-S-[(2R,3S,5R)-5-hydroxy-2-pentyltetrahydrofuran-3-yl]-L-cysteinylglycine                                                          
HAG "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[(2R,3S,5R)-5-hydroxy-2-pentyl-oxolan-3-yl]sulfanyl-1-oxo-propan-2-yl]amino]-5-oxo-pentanoic acid" 
# 
