data_BOB # _chem_comp.id BOB _chem_comp.name "(S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((3S,4R)-1,4-dihydroxynonan-3-ylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C19 H35 N3 O8 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms "L-gamma-glutamyl-S-[(1S,2R)-2-hydroxy-1-(2-hydroxyethyl)heptyl]-L-cysteinylglycine" _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2009-08-12 _chem_comp.pdbx_modified_date 2021-03-13 _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 465.562 _chem_comp.one_letter_code ? _chem_comp.three_letter_code BOB _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 3IK7 _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 BOB C1 C1 C 0 1 N N N 25.070 51.326 62.167 6.947 2.675 -0.405 C1 BOB 1 BOB N1 N1 N 0 1 N N N 26.148 49.779 60.630 5.575 2.296 -2.374 N1 BOB 2 BOB C2 C2 C 0 1 N N N 29.680 50.370 68.043 0.986 -2.503 -0.340 C2 BOB 3 BOB N2 N2 N 0 1 N N N 28.603 51.209 66.079 1.407 -0.117 -0.214 N2 BOB 4 BOB O2 O2 O 0 1 N N N 28.524 50.364 68.721 1.641 -2.464 -1.360 O2 BOB 5 BOB C3 C3 C 0 1 N N N 31.106 47.328 69.520 0.025 -6.058 -0.000 C3 BOB 6 BOB N3 N3 N 0 1 N N N 30.631 49.537 68.465 0.471 -3.674 0.085 N3 BOB 7 BOB O11 O11 O 0 1 N N N 25.183 52.194 61.288 7.875 2.243 -1.048 O11 BOB 8 BOB O12 O12 O 0 1 N N N 24.300 51.461 63.158 7.171 3.282 0.771 O12 BOB 9 BOB O31 O31 O 0 1 N N N 31.435 46.757 70.593 0.102 -7.289 -0.530 O31 BOB 10 BOB O32 O32 O 0 1 N N N 31.281 46.836 68.384 -0.588 -5.879 1.026 O32 BOB 11 BOB C40 C40 C 0 1 N N S 31.087 55.064 65.412 -2.836 0.771 1.371 C40 BOB 12 BOB C42 C42 C 0 1 N N R 32.258 54.238 64.813 -3.209 1.099 -0.076 C42 BOB 13 BOB C43 C43 C 0 1 N N N 33.692 54.589 65.248 -4.723 1.291 -0.182 C43 BOB 14 BOB C44 C44 C 0 1 N N N 34.103 54.094 66.641 -5.110 1.496 -1.648 C44 BOB 15 BOB C45 C45 C 0 1 N N N 35.407 53.295 66.649 -6.624 1.688 -1.754 C45 BOB 16 BOB C46 C46 C 0 1 N N N 36.619 54.101 67.126 -7.011 1.893 -3.220 C46 BOB 17 BOB C47 C47 C 0 1 N N N 37.740 54.060 66.108 -8.525 2.086 -3.326 C47 BOB 18 BOB C54 C54 C 0 1 N N N 31.418 56.123 66.498 -3.269 1.921 2.282 C54 BOB 19 BOB C55 C55 C 0 1 N N N 31.673 57.537 65.937 -3.020 1.536 3.742 C55 BOB 20 BOB O56 O56 O 0 1 N N N 31.533 58.581 66.931 -3.533 2.559 4.598 O56 BOB 21 BOB O60 O60 O 0 1 N N N 32.027 52.840 65.038 -2.546 2.300 -0.478 O60 BOB 22 BOB CA1 CA1 C 0 1 N N S 25.916 50.093 62.030 5.540 2.536 -0.925 CA1 BOB 23 BOB CA2 CA2 C 0 1 N N R 29.861 51.268 66.838 0.749 -1.244 0.452 CA2 BOB 24 BOB CA3 CA3 C 0 1 N N N 30.439 48.669 69.629 0.702 -4.899 -0.685 CA3 BOB 25 BOB CB1 CB1 C 0 1 N N N 27.264 50.318 62.718 4.852 1.359 -0.230 CB1 BOB 26 BOB CB2 CB2 C 0 1 N N N 30.161 52.731 67.241 -0.755 -0.974 0.543 CB2 BOB 27 BOB CD1 CD1 C 0 1 N N N 28.525 50.868 64.797 2.710 0.136 0.020 CD1 BOB 28 BOB OE1 OE1 O 0 1 N N N 29.629 50.594 64.095 3.338 -0.569 0.781 OE1 BOB 29 BOB CG1 CG1 C 0 1 N N N 27.157 50.807 64.162 3.387 1.295 -0.665 CG1 BOB 30 BOB SG2 SG2 S 0 1 N N N 29.803 53.958 65.995 -1.041 0.542 1.496 SG2 BOB 31 BOB HN1 HN1 H 0 1 N N N 26.712 48.956 60.561 5.966 3.088 -2.862 HN1 BOB 32 BOB HN1A HN1A H 0 0 N N N 25.272 49.621 60.174 6.084 1.452 -2.588 HN1A BOB 33 BOB HN2 HN2 H 0 1 N N N 27.755 51.439 66.556 0.905 0.447 -0.823 HN2 BOB 34 BOB HN3 HN3 H 0 1 N N N 31.501 49.504 67.973 -0.053 -3.705 0.901 HN3 BOB 35 BOB HO12 HO12 H 0 0 N N N 23.855 52.299 63.102 8.091 3.351 1.062 HO12 BOB 36 BOB HO31 HO31 H 0 0 N N N 31.827 45.914 70.396 -0.348 -8.000 -0.055 HO31 BOB 37 BOB H40 H40 H 0 1 N N N 30.755 55.683 64.565 -3.341 -0.146 1.677 H40 BOB 38 BOB H42 H42 H 0 1 N N N 32.236 54.515 63.749 -2.900 0.279 -0.726 H42 BOB 39 BOB H43 H43 H 0 1 N N N 34.379 54.133 64.520 -5.229 0.408 0.208 H43 BOB 40 BOB H43A H43A H 0 0 N N N 33.778 55.686 65.249 -5.019 2.166 0.397 H43A BOB 41 BOB H44 H44 H 0 1 N N N 34.236 54.972 67.290 -4.603 2.379 -2.038 H44 BOB 42 BOB H44A H44A H 0 0 N N N 33.302 53.444 67.023 -4.813 0.621 -2.228 H44A BOB 43 BOB H45 H45 H 0 1 N N N 35.278 52.438 67.327 -7.130 0.805 -1.364 H45 BOB 44 BOB H45A H45A H 0 0 N N N 35.606 52.955 65.622 -6.920 2.563 -1.174 H45A BOB 45 BOB H46 H46 H 0 1 N N N 36.314 55.147 67.278 -6.504 2.776 -3.610 H46 BOB 46 BOB H46A H46A H 0 0 N N N 36.981 53.673 68.072 -6.714 1.019 -3.799 H46A BOB 47 BOB H47 H47 H 0 1 N N N 38.594 54.646 66.478 -9.031 1.203 -2.936 H47 BOB 48 BOB H47A H47A H 0 0 N N N 38.053 53.017 65.949 -8.821 2.960 -2.746 H47A BOB 49 BOB H47B H47B H 0 0 N N N 37.387 54.486 65.157 -8.800 2.231 -4.370 H47B BOB 50 BOB H54 H54 H 0 1 N N N 30.564 56.180 67.189 -2.693 2.814 2.039 H54 BOB 51 BOB H54A H54A H 0 0 N N N 32.327 55.797 67.025 -4.330 2.122 2.135 H54A BOB 52 BOB H55 H55 H 0 1 N N N 32.700 57.571 65.545 -3.523 0.594 3.960 H55 BOB 53 BOB H55A H55A H 0 0 N N N 30.944 57.726 65.135 -1.949 1.424 3.911 H55A BOB 54 BOB HO56 HO56 H 0 0 N N N 31.701 59.426 66.530 -3.410 2.381 5.541 HO56 BOB 55 BOB HO60 HO60 H 0 0 N N N 32.744 52.337 64.671 -2.774 3.072 0.057 HO60 BOB 56 BOB HA1 HA1 H 0 1 N N N 25.383 49.254 62.501 4.986 3.452 -0.722 HA1 BOB 57 BOB HA2 HA2 H 0 1 N N N 30.720 50.924 66.243 1.158 -1.362 1.455 HA2 BOB 58 BOB HA3 HA3 H 0 1 N N N 29.359 48.500 69.749 1.773 -5.091 -0.750 HA3 BOB 59 BOB HA3A HA3A H 0 0 N N N 30.858 49.184 70.506 0.293 -4.780 -1.688 HA3A BOB 60 BOB HB1 HB1 H 0 1 N N N 27.805 49.360 62.724 5.354 0.431 -0.505 HB1 BOB 61 BOB HB1A HB1A H 0 0 N N N 27.815 51.077 62.143 4.905 1.495 0.850 HB1A BOB 62 BOB HB2 HB2 H 0 1 N N N 29.546 52.965 68.123 -1.164 -0.856 -0.460 HB2 BOB 63 BOB HB2A HB2A H 0 0 N N N 31.234 52.797 67.473 -1.245 -1.813 1.038 HB2A BOB 64 BOB HG1 HG1 H 0 1 N N N 26.709 51.811 64.171 2.885 2.223 -0.391 HG1 BOB 65 BOB HG1A HG1A H 0 0 N N N 26.524 50.112 64.733 3.335 1.160 -1.746 HG1A BOB 66 # # 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 BOB O11 C1 DOUB N N 1 BOB CA1 C1 SING N N 2 BOB C1 O12 SING N N 3 BOB N1 CA1 SING N N 4 BOB N1 HN1 SING N N 5 BOB N1 HN1A SING N N 6 BOB CA2 C2 SING N N 7 BOB C2 N3 SING N N 8 BOB C2 O2 DOUB N N 9 BOB CD1 N2 SING N N 10 BOB N2 CA2 SING N N 11 BOB N2 HN2 SING N N 12 BOB O32 C3 DOUB N N 13 BOB C3 CA3 SING N N 14 BOB C3 O31 SING N N 15 BOB N3 CA3 SING N N 16 BOB N3 HN3 SING N N 17 BOB O12 HO12 SING N N 18 BOB O31 HO31 SING N N 19 BOB C42 C40 SING N N 20 BOB C40 SG2 SING N N 21 BOB C40 C54 SING N N 22 BOB C40 H40 SING N N 23 BOB C42 O60 SING N N 24 BOB C42 C43 SING N N 25 BOB C42 H42 SING N N 26 BOB C43 C44 SING N N 27 BOB C43 H43 SING N N 28 BOB C43 H43A SING N N 29 BOB C44 C45 SING N N 30 BOB C44 H44 SING N N 31 BOB C44 H44A SING N N 32 BOB C45 C46 SING N N 33 BOB C45 H45 SING N N 34 BOB C45 H45A SING N N 35 BOB C47 C46 SING N N 36 BOB C46 H46 SING N N 37 BOB C46 H46A SING N N 38 BOB C47 H47 SING N N 39 BOB C47 H47A SING N N 40 BOB C47 H47B SING N N 41 BOB C55 C54 SING N N 42 BOB C54 H54 SING N N 43 BOB C54 H54A SING N N 44 BOB C55 O56 SING N N 45 BOB C55 H55 SING N N 46 BOB C55 H55A SING N N 47 BOB O56 HO56 SING N N 48 BOB O60 HO60 SING N N 49 BOB CA1 CB1 SING N N 50 BOB CA1 HA1 SING N N 51 BOB CA2 CB2 SING N N 52 BOB CA2 HA2 SING N N 53 BOB CA3 HA3 SING N N 54 BOB CA3 HA3A SING N N 55 BOB CB1 CG1 SING N N 56 BOB CB1 HB1 SING N N 57 BOB CB1 HB1A SING N N 58 BOB SG2 CB2 SING N N 59 BOB CB2 HB2 SING N N 60 BOB CB2 HB2A SING N N 61 BOB OE1 CD1 DOUB N N 62 BOB CG1 CD1 SING N N 63 BOB CG1 HG1 SING N N 64 BOB CG1 HG1A SING N N 65 # # 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 BOB SMILES ACDLabs 11.02 "O=C(NC(C(=O)NCC(=O)O)CSC(C(O)CCCCC)CCO)CCC(C(=O)O)N" BOB SMILES_CANONICAL CACTVS 3.352 "CCCCC[C@@H](O)[C@H](CCO)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O" BOB SMILES CACTVS 3.352 "CCCCC[CH](O)[CH](CCO)SC[CH](NC(=O)CC[CH](N)C(O)=O)C(=O)NCC(O)=O" BOB SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "CCCCC[C@H]([C@H](CCO)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)O" BOB SMILES "OpenEye OEToolkits" 1.7.0 "CCCCCC(C(CCO)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)O" BOB InChI InChI 1.03 "InChI=1S/C19H35N3O8S/c1-2-3-4-5-14(24)15(8-9-23)31-11-13(18(28)21-10-17(26)27)22-16(25)7-6-12(20)19(29)30/h12-15,23-24H,2-11,20H2,1H3,(H,21,28)(H,22,25)(H,26,27)(H,29,30)/t12-,13-,14+,15-/m0/s1" BOB InChIKey InChI 1.03 CLEVVMDJDMEQKG-XQLPTFJDSA-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 BOB "SYSTEMATIC NAME" ACDLabs 11.02 "L-gamma-glutamyl-S-[(3S,4R)-1,4-dihydroxynonan-3-yl]-L-cysteinylglycine" BOB "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.6.1 "(2S)-2-azanyl-5-[[(2R)-1-(carboxymethylamino)-3-[(3S,4R)-1,4-dihydroxynonan-3-yl]sulfanyl-1-oxo-propan-2-yl]amino]-5-oxo-pentanoic acid" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site BOB "Create component" 2009-08-12 RCSB BOB "Modify descriptor" 2011-06-04 RCSB BOB "Modify synonyms" 2021-03-13 RCSB # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id BOB _pdbx_chem_comp_synonyms.name "L-gamma-glutamyl-S-[(1S,2R)-2-hydroxy-1-(2-hydroxyethyl)heptyl]-L-cysteinylglycine" _pdbx_chem_comp_synonyms.provenance PDB _pdbx_chem_comp_synonyms.type ? ##