data_bmse010468 save_entry_information _Entry.Sf_category entry_information _Entry.Sf_framecode entry_information _Entry.ID bmse010468 _Entry.Title lignin_cw_compound_2025 _Entry.Version_type original _Entry.Submission_date 2009-05-26 _Entry.Accession_date 2013-01-09 _Entry.Last_release_date 2013-01-17 _Entry.Original_release_date 2013-01-17 _Entry.Origination author _Entry.NMR_STAR_version 3.1.1.31 _Entry.Original_NMR_STAR_version 3.1.0.46 _Entry.Experimental_method NMR _Entry.Experimental_method_subtype solution _Entry.Details ? _Entry.BMRB_internal_directory_name lignin_cw_compound_2025 loop_ _Entry_author.Ordinal _Entry_author.Given_name _Entry_author.Family_name _Entry_author.Middle_initials _Entry_author.Family_title _Entry_author.Entry_ID 1 John Ralph ? ? bmse010468 2 Sally Ralph ? ? bmse010468 3 Stephane Quideau ? ? bmse010468 stop_ loop_ _Entry_src.ID _Entry_src.Project_name _Entry_src.Organization_full_name _Entry_src.Organization_initials _Entry_src.Entry_ID 1 "NMR Database of Lignin and Cell Wall Model Compounds" "United States Department of Agriculture" USDA bmse010468 stop_ loop_ _Data_set.Type _Data_set.Count _Data_set.Entry_ID assigned_chemical_shifts 1 bmse010468 stop_ loop_ _Datum.Type _Datum.Count _Datum.Entry_ID "13C chemical shifts" 39 bmse010468 "1H chemical shifts" 8 bmse010468 stop_ loop_ _Release.Release_number _Release.Date _Release.Submission_date _Release.Type _Release.Author _Release.Detail _Release.Entry_ID 1 2013-01-17 2009-05-26 original BMRB "Original spectra from MMC" bmse010468 stop_ save_ save_citation_1 _Citation.Sf_category citations _Citation.Sf_framecode citation_1 _Citation.Entry_ID bmse010468 _Citation.ID 1 _Citation.Class 'entry citation' _Citation.PubMed_ID ? _Citation.Title 'NMR Database of Lignin and Cell Wall Model Compounds.' _Citation.Status published _Citation.Type internet _Citation.WWW_URL http://ars.usda.gov/Services/docs.htm?docid=10491 _Citation.Year 2004 _Citation.Details ? loop_ _Citation_author.Ordinal _Citation_author.Given_name _Citation_author.Family_name _Citation_author.First_initial _Citation_author.Middle_initials _Citation_author.Family_title _Citation_author.Entry_ID _Citation_author.Citation_ID 1 Sally Ralph ? A. ? bmse010468 1 2 John Ralph ? ? ? bmse010468 1 3 Larry Landucci ? L. ? bmse010468 1 stop_ save_ save_assembly _Assembly.Sf_category assembly _Assembly.Sf_framecode assembly _Assembly.Entry_ID bmse010468 _Assembly.ID 1 _Assembly.Name lignin_cw_compound_2025 _Assembly.Number_of_components 1 _Assembly.Organic_ligands 0 _Assembly.Metal_ions ? _Assembly.Non_standard_bonds no _Assembly.Paramagnetic no _Assembly.Thiol_state 'not reported' loop_ _Entity_assembly.ID _Entity_assembly.Entity_assembly_name _Entity_assembly.Entity_ID _Entity_assembly.Entity_label _Entity_assembly.Experimental_data_reported _Entity_assembly.Physical_state _Entity_assembly.Conformational_isomer _Entity_assembly.Chemical_exchange_state _Entity_assembly.Magnetic_equivalence_group_code _Entity_assembly.Role _Entity_assembly.Details _Entity_assembly.Entry_ID _Entity_assembly.Assembly_ID 1 lignin_cw_compound_2025 1 $lignin_cw_compound_2025 yes native no no ? ? ? bmse010468 1 stop_ save_ save_lignin_cw_compound_2025 _Entity.Sf_category entity _Entity.Sf_framecode lignin_cw_compound_2025 _Entity.Entry_ID bmse010468 _Entity.ID 1 _Entity.BMRB_code ? _Entity.Name lignin_cw_compound_2025 _Entity.Type non-polymer _Entity.Ambiguous_conformational_states no _Entity.Ambiguous_chem_comp_sites no _Entity.Nstd_monomer no _Entity.Nstd_chirality no _Entity.Nstd_linkage no _Entity.Paramagnetic no _Entity.Thiol_state 'not reported' loop_ _Entity_comp_index.ID _Entity_comp_index.Comp_ID _Entity_comp_index.Comp_label _Entity_comp_index.Entry_ID _Entity_comp_index.Entity_ID 1 1 $chem_comp_1 bmse010468 1 stop_ save_ save_natural_source _Entity_natural_src_list.Sf_category natural_source _Entity_natural_src_list.Sf_framecode natural_source _Entity_natural_src_list.Entry_ID bmse010468 _Entity_natural_src_list.ID 1 loop_ _Entity_natural_src.ID _Entity_natural_src.Entity_ID _Entity_natural_src.Entity_label _Entity_natural_src.Entity_chimera_segment_ID _Entity_natural_src.NCBI_taxonomy_ID _Entity_natural_src.Type _Entity_natural_src.Common _Entity_natural_src.Organism_name_scientific _Entity_natural_src.Organism_name_common _Entity_natural_src.Organism_acronym _Entity_natural_src.ICTVdb_decimal_code _Entity_natural_src.Superkingdom _Entity_natural_src.Kingdom _Entity_natural_src.Genus _Entity_natural_src.Species _Entity_natural_src.Strain _Entity_natural_src.Variant _Entity_natural_src.Subvariant _Entity_natural_src.Organ _Entity_natural_src.Tissue _Entity_natural_src.Tissue_fraction _Entity_natural_src.Cell_line _Entity_natural_src.Cell_type _Entity_natural_src.ATCC_number _Entity_natural_src.Organelle _Entity_natural_src.Cellular_location _Entity_natural_src.Fragment _Entity_natural_src.Fraction _Entity_natural_src.Secretion _Entity_natural_src.Plasmid _Entity_natural_src.Plasmid_details _Entity_natural_src.Gene_mnemonic _Entity_natural_src.Dev_stage _Entity_natural_src.Details _Entity_natural_src.Citation_ID _Entity_natural_src.Citation_label _Entity_natural_src.Entry_ID _Entity_natural_src.Entity_natural_src_list_ID 1 1 $lignin_cw_compound_2025 . n/a "multiple natural sources" yes "not applicable" n/a . . Eukaryota Viridiplantae n/a n/a . . . . . . . . . . . . . . . . . . . . . bmse010468 1 stop_ save_ save_experimental_source _Entity_experimental_src_list.Sf_category experimental_source _Entity_experimental_src_list.Sf_framecode experimental_source _Entity_experimental_src_list.Entry_ID bmse010468 _Entity_experimental_src_list.ID 1 loop_ _Entity_experimental_src.ID _Entity_experimental_src.Entity_ID _Entity_experimental_src.Entity_label _Entity_experimental_src.Entity_chimera_segment_ID _Entity_experimental_src.Production_method _Entity_experimental_src.Host_org_scientific_name _Entity_experimental_src.Host_org_name_common _Entity_experimental_src.Host_org_details _Entity_experimental_src.Host_org_NCBI_taxonomy_ID _Entity_experimental_src.Host_org_genus _Entity_experimental_src.Host_org_species _Entity_experimental_src.Host_org_strain _Entity_experimental_src.Host_org_variant _Entity_experimental_src.Host_org_subvariant _Entity_experimental_src.Host_org_organ _Entity_experimental_src.Host_org_tissue _Entity_experimental_src.Host_org_tissue_fraction _Entity_experimental_src.Host_org_cell_line _Entity_experimental_src.Host_org_cell_type _Entity_experimental_src.Host_org_cellular_location _Entity_experimental_src.Host_org_organelle _Entity_experimental_src.Host_org_gene _Entity_experimental_src.Host_org_culture_collection _Entity_experimental_src.Host_org_ATCC_number _Entity_experimental_src.Vector_type _Entity_experimental_src.PDBview_host_org_vector_name _Entity_experimental_src.PDBview_plasmid_name _Entity_experimental_src.Vector_name _Entity_experimental_src.Vector_details _Entity_experimental_src.Vendor_name _Entity_experimental_src.Host_org_dev_stage _Entity_experimental_src.Details _Entity_experimental_src.Citation_ID _Entity_experimental_src.Citation_label _Entity_experimental_src.Entry_ID _Entity_experimental_src.Entity_experimental_src_list_ID 1 1 $lignin_cw_compound_2025 . "chemical synthesis" . . . . . . . . . . . . . . . . . . . . . . . . . . . . . bmse010468 1 stop_ save_ save_chem_comp_1 _Chem_comp.Sf_category chem_comp _Chem_comp.Sf_framecode chem_comp_1 _Chem_comp.Entry_ID bmse010468 _Chem_comp.ID 1 _Chem_comp.Provenance BMRB _Chem_comp.Name lignin_cw_compound_2025 _Chem_comp.Type non-polymer _Chem_comp.BMRB_code bmse010468 _Chem_comp.PDB_code ? _Chem_comp.InCHi_code ; InChI=1/C42H48O12/c1-41-23-52-40(42(41,2)24-51-39(41)27-11-14-30(46)34(20-27)48-4)28-12-16-32(36(21-28)50-6)54-38(26-10-13-29(45)33(19-26)47-3)37(22-44)53-31-15-9-25(8-7-17-43)18-35(31)49-5/h7-16,18-21,37-40,43-46H,17,22-24H2,1-6H3/b8-7+/t37-,38+,39-,40-,41-,42-/m0/s1 ; _Chem_comp.Mon_nstd_flag ? _Chem_comp.Std_deriv_one_letter_code ? _Chem_comp.Std_deriv_three_letter_code ? _Chem_comp.Std_deriv_BMRB_code ? _Chem_comp.Std_deriv_PDB_code ? _Chem_comp.Formal_charge ? _Chem_comp.Paramagnetic no _Chem_comp.Aromatic yes _Chem_comp.Formula 'C42 H48 O12' _Chem_comp.Formula_weight 744.82332 _Chem_comp.Formula_mono_iso_wt_nat 744.314577006 _Chem_comp.Formula_mono_iso_wt_13C 786.4554801936 _Chem_comp.Formula_mono_iso_wt_15N 744.314577006 _Chem_comp.Formula_mono_iso_wt_13C_15N 786.4554801936 _Chem_comp.Image_file_name standards/lignin_cw_compound_2025/lit/jr_2025.png _Chem_comp.Image_file_format png _Chem_comp.Topo_file_name ? _Chem_comp.Topo_file_format ? _Chem_comp.Struct_file_name standards/lignin_cw_compound_2025/lit/jr_2025.mol _Chem_comp.Struct_file_format MDL _Chem_comp.Stereochem_param_file_name ? _Chem_comp.Details ? _Chem_comp.DB_query_date ? _Chem_comp.DB_last_query_revised_last_date ? loop_ _Chem_comp_common_name.Name _Chem_comp_common_name.Type _Chem_comp_common_name.Entry_ID _Chem_comp_common_name.Comp_ID "Guaiacylglycerol-A-pinoresinol-B-coniferyl-bis-ether diastereomeric mixture" synonym bmse010468 1 stop_ loop_ _Chem_comp_systematic_name.Name _Chem_comp_systematic_name.Naming_system _Chem_comp_systematic_name.Entry_ID _Chem_comp_systematic_name.Comp_ID "Guaiacylglycerol-A-pinoresinol-B-coniferyl-bis-ether diastereomeric mixture" Beilstein bmse010468 1 stop_ loop_ _Chem_comp_SMILES.Type _Chem_comp_SMILES.String _Chem_comp_SMILES.Entry_ID _Chem_comp_SMILES.Comp_ID Canonical ; C[C@@]45CO[C@@H](C1=CC(=C(C=C1)O[C@H](C2=CC(=C(C=C2)O)OC)[C@H](CO)OC3=C(C=C(C=CCO)C=C3)OC)OC)[C@]4(C)CO[C@H]5C6=CC(=C(C=C6)O)OC ; bmse010468 1 Isomeric ; C[C@@]45CO[C@@H](C1=CC(=C(C=C1)O[C@H](C2=CC(=C(C=C2)O)OC)[C@H](CO)OC3=C(C=C(C=CCO)C=C3)OC)OC)[C@]4(C)CO[C@H]5C6=CC(=C(C=C6)O)OC ; bmse010468 1 stop_ loop_ _Chem_comp_atom.Atom_ID _Chem_comp_atom.Auth_atom_ID _Chem_comp_atom.Type_symbol _Chem_comp_atom.Stereo_config _Chem_comp_atom.Charge _Chem_comp_atom.Oxidation_number _Chem_comp_atom.Unpaired_electron_number _Chem_comp_atom.Drawing_2D_coord_x _Chem_comp_atom.Drawing_2D_coord_y _Chem_comp_atom.Model_Cartn_x _Chem_comp_atom.Model_Cartn_y _Chem_comp_atom.Model_Cartn_z _Chem_comp_atom.Entry_ID _Chem_comp_atom.Comp_ID C1 ? C ? ? ? ? 373.3905 105.7548 ? ? ? bmse010468 1 C2 ? C ? ? ? ? 373.3905 183.7548 ? ? ? bmse010468 1 C3 ? C ? ? ? ? 216.1269 355.0974 ? ? ? bmse010468 1 C4 ? C ? ? ? ? 387.4955 10.9874 ? ? ? bmse010468 1 C5 ? C ? ? ? ? 171.9685 272.4044 ? ? ? bmse010468 1 C6 ? C ? ? ? ? 359.3557 278.6132 ? ? ? bmse010468 1 C7 ? C ? ? ? ? 153.2433 184.3060 ? ? ? bmse010468 1 C8 ? C ? ? ? ? 178.6739 178.9006 ? ? ? bmse010468 1 C9 ? C ? ? ? ? 221.5037 192.8158 ? ? ? bmse010468 1 C10 ? C ? ? ? ? 300.4553 314.1526 ? ? ? bmse010468 1 C11 ? C ? ? ? ? 431.5109 93.7558 ? ? ? bmse010468 1 C12 ? C ? ? ? ? 315.1973 195.9202 ? ? ? bmse010468 1 C13 ? C ? ? ? ? 292.4213 338.8812 ? ? ? bmse010468 1 C14 ? C ? ? ? ? 439.5865 69.0428 ? ? ? bmse010468 1 C15 ? C ? ? ? ? 238.9003 212.1390 ? ? ? bmse010468 1 C16 ? C ? ? ? ? 307.1633 220.6488 ? ? ? bmse010468 1 C17 ? C ? ? ? ? 135.8441 164.9854 ? ? ? bmse010468 1 C18 ? C ? ? ? ? 188.0365 222.9498 ? ? ? bmse010468 1 C19 ? C ? ? ? ? 257.6281 300.2374 ? ? ? bmse010468 1 C20 ? C ? ? ? ? 388.7045 79.7652 ? ? ? bmse010468 1 C21 ? C ? ? ? ? 358.0271 209.8380 ? ? ? bmse010468 1 C22 ? C ? ? ? ? 281.7301 226.0542 ? ? ? bmse010468 1 C23 ? C ? ? ? ? 348.6619 123.7182 ? ? ? bmse010468 1 C24 ? C ? ? ? ? 397.9917 165.6770 ? ? ? bmse010468 1 C25 ? C ? ? ? ? 196.0731 198.2212 ? ? ? bmse010468 1 C26 ? C ? ? ? ? 283.0587 294.8320 ? ? ? bmse010468 1 C27 ? C ? ? ? ? 406.0699 99.1170 ? ? ? bmse010468 1 C28 ? C ? ? ? ? 340.6279 190.5148 ? ? ? bmse010468 1 C29 ? C ? ? ? ? 266.9907 344.2866 ? ? ? bmse010468 1 C30 ? C ? ? ? ? 422.2237 49.6910 ? ? ? bmse010468 1 C31 ? C ? ? ? ? 230.8663 236.8650 ? ? ? bmse010468 1 C32 ? C ? ? ? ? 324.5599 239.9694 ? ? ? bmse010468 1 C33 ? C ? ? ? ? 249.5915 324.9634 ? ? ? bmse010468 1 C34 ? C ? ? ? ? 396.7827 55.0522 ? ? ? bmse010468 1 C35 ? C ? ? ? ? 205.4357 242.2704 ? ? ? bmse010468 1 C36 ? C ? ? ? ? 349.9905 234.5640 ? ? ? bmse010468 1 C37 ? C ? ? ? ? 273.6961 250.7828 ? ? ? bmse010468 1 C38 ? C ? ? ? ? 291.0927 270.1034 ? ? ? bmse010468 1 C39 ? C ? ? ? ? 397.9917 123.8300 ? ? ? bmse010468 1 C40 ? C ? ? ? ? 348.6619 165.7888 ? ? ? bmse010468 1 C41 ? C ? ? ? ? 373.3905 131.7548 ? ? ? bmse010468 1 C42 ? C ? ? ? ? 373.3905 157.7548 ? ? ? bmse010468 1 O43 ? O ? ? ? ? 110.4135 170.3908 ? ? ? bmse010468 1 O44 ? O ? ? ? ? 264.3335 206.7336 ? ? ? bmse010468 1 O45 ? O ? ? ? ? 258.9567 369.0126 ? ? ? bmse010468 1 O46 ? O ? ? ? ? 430.3019 24.9754 ? ? ? bmse010468 1 O47 ? O ? ? ? ? 224.1609 330.3688 ? ? ? bmse010468 1 O48 ? O ? ? ? ? 379.4199 35.7004 ? ? ? bmse010468 1 O49 ? O ? ? ? ? 197.4017 266.9990 ? ? ? bmse010468 1 O50 ? O ? ? ? ? 367.3897 253.8872 ? ? ? bmse010468 1 O51 ? O ? ? ? ? 413.1653 144.7548 ? ? ? bmse010468 1 O52 ? O ? ? ? ? 333.3817 144.7548 ? ? ? bmse010468 1 O53 ? O ? ? ? ? 248.2629 256.1882 ? ? ? bmse010468 1 O54 ? O ? ? ? ? 316.5259 264.6980 ? ? ? bmse010468 1 H55 ? H ? ? ? ? 357.2705 105.7548 ? ? ? bmse010468 1 H56 ? H ? ? ? ? 373.3905 89.6348 ? ? ? bmse010468 1 H57 ? H ? ? ? ? 389.5105 105.7548 ? ? ? bmse010468 1 H58 ? H ? ? ? ? 389.5105 183.7548 ? ? ? bmse010468 1 H59 ? H ? ? ? ? 373.3905 199.8748 ? ? ? bmse010468 1 H60 ? H ? ? ? ? 357.2705 183.7548 ? ? ? bmse010468 1 H61 ? H ? ? ? ? 231.4581 360.0783 ? ? ? bmse010468 1 H62 ? H ? ? ? ? 211.1460 370.4286 ? ? ? bmse010468 1 H63 ? H ? ? ? ? 200.7957 350.1165 ? ? ? bmse010468 1 H64 ? H ? ? ? ? 372.1729 5.9803 ? ? ? bmse010468 1 H65 ? H ? ? ? ? 392.5026 -4.3352 ? ? ? bmse010468 1 H66 ? H ? ? ? ? 402.8182 15.9945 ? ? ? bmse010468 1 H67 ? H ? ? ? ? 175.3197 288.1722 ? ? ? bmse010468 1 H68 ? H ? ? ? ? 156.2007 275.7556 ? ? ? bmse010468 1 H69 ? H ? ? ? ? 168.6173 256.6366 ? ? ? bmse010468 1 H70 ? H ? ? ? ? 374.6867 283.5946 ? ? ? bmse010468 1 H71 ? H ? ? ? ? 354.3743 293.9442 ? ? ? bmse010468 1 H72 ? H ? ? ? ? 344.0247 273.6318 ? ? ? bmse010468 1 H73 ? H ? ? ? ? 148.2626 199.6372 ? ? ? bmse010468 1 H74 ? H ? ? ? ? 183.6546 163.5694 ? ? ? bmse010468 1 H75 ? H ? ? ? ? 226.4855 177.4849 ? ? ? bmse010468 1 H76 ? H ? ? ? ? 316.2230 310.8008 ? ? ? bmse010468 1 H77 ? H ? ? ? ? 442.2768 105.7537 ? ? ? bmse010468 1 H78 ? H ? ? ? ? 304.4107 183.9409 ? ? ? bmse010468 1 H79 ? H ? ? ? ? 303.2079 350.8605 ? ? ? bmse010468 1 H80 ? H ? ? ? ? 455.3600 65.7184 ? ? ? bmse010468 1 H81 ? H ? ? ? ? 254.6681 208.7879 ? ? ? bmse010468 1 H82 ? H ? ? ? ? 291.3956 224.0006 ? ? ? bmse010468 1 H83 ? H ? ? ? ? 129.8051 150.0394 ? ? ? bmse010468 1 H84 ? H ? ? ? ? 149.5142 156.4424 ? ? ? bmse010468 1 H85 ? H ? ? ? ? 172.2688 226.3015 ? ? ? bmse010468 1 H86 ? H ? ? ? ? 246.8423 288.2574 ? ? ? bmse010468 1 H87 ? H ? ? ? ? 372.9310 83.0894 ? ? ? bmse010468 1 H88 ? H ? ? ? ? 373.7950 206.4871 ? ? ? bmse010468 1 H89 ? H ? ? ? ? 291.6544 213.3513 ? ? ? bmse010468 1 H90 ? H ? ? ? ? 295.9634 233.6218 ? ? ? bmse010468 1 H91 ? H ? ? ? ? 334.7011 115.6590 ? ? ? bmse010468 1 H92 ? H ? ? ? ? 355.2186 108.9919 ? ? ? bmse010468 1 H93 ? H ? ? ? ? 411.9637 173.7169 ? ? ? bmse010468 1 H94 ? H ? ? ? ? 391.4650 180.4166 ? ? ? bmse010468 1 H95 ? H ? ? ? ? 268.7146 266.1138 ? ? ? bmse010468 1 H96 ? H ? ? ? ? 296.0742 254.7724 ? ? ? bmse010468 1 H97 ? H ? ? ? ? 386.6176 112.4070 ? ? ? bmse010468 1 H98 ? H ? ? ? ? 332.7403 168.3100 ? ? ? bmse010468 1 H99 ? H ? ? ? ? 105.4321 185.7218 ? ? ? bmse010468 1 H100 ? H ? ? ? ? 248.5658 210.0853 ? ? ? bmse010468 1 H101 ? H ? ? ? ? 269.7431 380.9921 ? ? ? bmse010468 1 H102 ? H ? ? ? ? 419.5364 12.9771 ? ? ? bmse010468 1 stop_ loop_ _Atom_nomenclature.Atom_ID _Atom_nomenclature.Atom_name _Atom_nomenclature.Naming_system _Atom_nomenclature.Entry_ID _Atom_nomenclature.Comp_ID C1 C1 ? bmse010468 1 C2 C2 ? bmse010468 1 C3 C3 ? bmse010468 1 C4 C4 ? bmse010468 1 C5 C5 ? bmse010468 1 C6 C6 ? bmse010468 1 C7 C7 ? bmse010468 1 C8 C8 ? bmse010468 1 C9 C9 ? bmse010468 1 C10 C10 ? bmse010468 1 C11 C11 ? bmse010468 1 C12 C12 ? bmse010468 1 C13 C13 ? bmse010468 1 C14 C14 ? bmse010468 1 C15 C15 ? bmse010468 1 C16 C16 ? bmse010468 1 C17 C17 ? bmse010468 1 C18 C18 ? bmse010468 1 C19 C19 ? bmse010468 1 C20 C20 ? bmse010468 1 C21 C21 ? bmse010468 1 C22 C22 ? bmse010468 1 C23 C23 ? bmse010468 1 C24 C24 ? bmse010468 1 C25 C25 ? bmse010468 1 C26 C26 ? bmse010468 1 C27 C27 ? bmse010468 1 C28 C28 ? bmse010468 1 C29 C29 ? bmse010468 1 C30 C30 ? bmse010468 1 C31 C31 ? bmse010468 1 C32 C32 ? bmse010468 1 C33 C33 ? bmse010468 1 C34 C34 ? bmse010468 1 C35 C35 ? bmse010468 1 C36 C36 ? bmse010468 1 C37 C37 ? bmse010468 1 C38 C38 ? bmse010468 1 C39 C39 ? bmse010468 1 C40 C40 ? bmse010468 1 C41 C41 ? bmse010468 1 C42 C42 ? bmse010468 1 O43 O43 ? bmse010468 1 O44 O44 ? bmse010468 1 O45 O45 ? bmse010468 1 O46 O46 ? bmse010468 1 O47 O47 ? bmse010468 1 O48 O48 ? bmse010468 1 O49 O49 ? bmse010468 1 O50 O50 ? bmse010468 1 O51 O51 ? bmse010468 1 O52 O52 ? bmse010468 1 O53 O53 ? bmse010468 1 O54 O54 ? bmse010468 1 H55 H55 ? bmse010468 1 H56 H56 ? bmse010468 1 H57 H57 ? bmse010468 1 H58 H58 ? bmse010468 1 H59 H59 ? bmse010468 1 H60 H60 ? bmse010468 1 H61 H61 ? bmse010468 1 H62 H62 ? bmse010468 1 H63 H63 ? bmse010468 1 H64 H64 ? bmse010468 1 H65 H65 ? bmse010468 1 H66 H66 ? bmse010468 1 H67 H67 ? bmse010468 1 H68 H68 ? bmse010468 1 H69 H69 ? bmse010468 1 H70 H70 ? bmse010468 1 H71 H71 ? bmse010468 1 H72 H72 ? bmse010468 1 H73 H73 ? bmse010468 1 H74 H74 ? bmse010468 1 H75 H75 ? bmse010468 1 H76 H76 ? bmse010468 1 H77 H77 ? bmse010468 1 H78 H78 ? bmse010468 1 H79 H79 ? bmse010468 1 H80 H80 ? bmse010468 1 H81 H81 ? bmse010468 1 H82 H82 ? bmse010468 1 H83 H83 ? bmse010468 1 H84 H84 ? bmse010468 1 H85 H85 ? bmse010468 1 H86 H86 ? bmse010468 1 H87 H87 ? bmse010468 1 H88 H88 ? bmse010468 1 H89 H89 ? bmse010468 1 H90 H90 ? bmse010468 1 H91 H91 ? bmse010468 1 H92 H92 ? bmse010468 1 H93 H93 ? bmse010468 1 H94 H94 ? bmse010468 1 H95 H95 ? bmse010468 1 H96 H96 ? bmse010468 1 H97 H97 ? bmse010468 1 H98 H98 ? bmse010468 1 H99 H99 ? bmse010468 1 H100 H100 ? bmse010468 1 H101 H101 ? bmse010468 1 H102 H102 ? bmse010468 1 stop_ loop_ _Chem_comp_bond.ID _Chem_comp_bond.Type _Chem_comp_bond.Value_order _Chem_comp_bond.Atom_ID_1 _Chem_comp_bond.Atom_ID_2 _Chem_comp_bond.Details _Chem_comp_bond.Entry_ID _Chem_comp_bond.Comp_ID 1 covalent SING C41 C1 ? bmse010468 1 2 covalent SING C42 C2 ? bmse010468 1 3 covalent SING C3 O47 ? bmse010468 1 4 covalent SING C4 O48 ? bmse010468 1 5 covalent SING C5 O49 ? bmse010468 1 6 covalent SING C6 O50 ? bmse010468 1 7 covalent DOUB C7 C8 ? bmse010468 1 8 covalent SING C7 C17 ? bmse010468 1 9 covalent SING C8 C25 ? bmse010468 1 10 covalent DOUB C9 C15 ? bmse010468 1 11 covalent SING C9 C25 ? bmse010468 1 12 covalent DOUB C10 C13 ? bmse010468 1 13 covalent SING C10 C26 ? bmse010468 1 14 covalent DOUB C11 C14 ? bmse010468 1 15 covalent SING C11 C27 ? bmse010468 1 16 covalent DOUB C12 C16 ? bmse010468 1 17 covalent SING C12 C28 ? bmse010468 1 18 covalent SING C13 C29 ? bmse010468 1 19 covalent SING C14 C30 ? bmse010468 1 20 covalent SING C15 C31 ? bmse010468 1 21 covalent SING C16 C32 ? bmse010468 1 22 covalent SING C17 O43 ? bmse010468 1 23 covalent DOUB C18 C25 ? bmse010468 1 24 covalent SING C18 C35 ? bmse010468 1 25 covalent DOUB C19 C26 ? bmse010468 1 26 covalent SING C19 C33 ? bmse010468 1 27 covalent DOUB C20 C27 ? bmse010468 1 28 covalent SING C20 C34 ? bmse010468 1 29 covalent DOUB C21 C28 ? bmse010468 1 30 covalent SING C21 C36 ? bmse010468 1 31 covalent SING C22 C37 ? bmse010468 1 32 covalent SING C22 O44 ? bmse010468 1 33 covalent SING C23 C41 ? bmse010468 1 34 covalent SING C23 O52 ? bmse010468 1 35 covalent SING C24 C42 ? bmse010468 1 36 covalent SING C24 O51 ? bmse010468 1 37 covalent SING C26 C38 ? bmse010468 1 38 covalent SING C39 C27 ? bmse010468 1 39 covalent SING C40 C28 ? bmse010468 1 40 covalent DOUB C29 C33 ? bmse010468 1 41 covalent SING C29 O45 ? bmse010468 1 42 covalent DOUB C30 C34 ? bmse010468 1 43 covalent SING C30 O46 ? bmse010468 1 44 covalent DOUB C31 C35 ? bmse010468 1 45 covalent SING C31 O53 ? bmse010468 1 46 covalent DOUB C32 C36 ? bmse010468 1 47 covalent SING C32 O54 ? bmse010468 1 48 covalent SING C33 O47 ? bmse010468 1 49 covalent SING C34 O48 ? bmse010468 1 50 covalent SING C35 O49 ? bmse010468 1 51 covalent SING C36 O50 ? bmse010468 1 52 covalent SING C37 C38 ? bmse010468 1 53 covalent SING C37 O53 ? bmse010468 1 54 covalent SING C38 O54 ? bmse010468 1 55 covalent SING C39 C41 ? bmse010468 1 56 covalent SING C39 O51 ? bmse010468 1 57 covalent SING C40 C42 ? bmse010468 1 58 covalent SING C40 O52 ? bmse010468 1 59 covalent SING C41 C42 ? bmse010468 1 60 covalent SING C1 H55 ? bmse010468 1 61 covalent SING C1 H56 ? bmse010468 1 62 covalent SING C1 H57 ? bmse010468 1 63 covalent SING C2 H58 ? bmse010468 1 64 covalent SING C2 H59 ? bmse010468 1 65 covalent SING C2 H60 ? bmse010468 1 66 covalent SING C3 H61 ? bmse010468 1 67 covalent SING C3 H62 ? bmse010468 1 68 covalent SING C3 H63 ? bmse010468 1 69 covalent SING C4 H64 ? bmse010468 1 70 covalent SING C4 H65 ? bmse010468 1 71 covalent SING C4 H66 ? bmse010468 1 72 covalent SING C5 H67 ? bmse010468 1 73 covalent SING C5 H68 ? bmse010468 1 74 covalent SING C5 H69 ? bmse010468 1 75 covalent SING C6 H70 ? bmse010468 1 76 covalent SING C6 H71 ? bmse010468 1 77 covalent SING C6 H72 ? bmse010468 1 78 covalent SING C7 H73 ? bmse010468 1 79 covalent SING C8 H74 ? bmse010468 1 80 covalent SING C9 H75 ? bmse010468 1 81 covalent SING C10 H76 ? bmse010468 1 82 covalent SING C11 H77 ? bmse010468 1 83 covalent SING C12 H78 ? bmse010468 1 84 covalent SING C13 H79 ? bmse010468 1 85 covalent SING C14 H80 ? bmse010468 1 86 covalent SING C15 H81 ? bmse010468 1 87 covalent SING C16 H82 ? bmse010468 1 88 covalent SING C17 H83 ? bmse010468 1 89 covalent SING C17 H84 ? bmse010468 1 90 covalent SING C18 H85 ? bmse010468 1 91 covalent SING C19 H86 ? bmse010468 1 92 covalent SING C20 H87 ? bmse010468 1 93 covalent SING C21 H88 ? bmse010468 1 94 covalent SING C22 H89 ? bmse010468 1 95 covalent SING C22 H90 ? bmse010468 1 96 covalent SING C23 H91 ? bmse010468 1 97 covalent SING C23 H92 ? bmse010468 1 98 covalent SING C24 H93 ? bmse010468 1 99 covalent SING C24 H94 ? bmse010468 1 100 covalent SING C37 H95 ? bmse010468 1 101 covalent SING C38 H96 ? bmse010468 1 102 covalent SING C39 H97 ? bmse010468 1 103 covalent SING C40 H98 ? bmse010468 1 104 covalent SING O43 H99 ? bmse010468 1 105 covalent SING O44 H100 ? bmse010468 1 106 covalent SING O45 H101 ? bmse010468 1 107 covalent SING O46 H102 ? bmse010468 1 stop_ loop_ _Chem_comp_db_link.Author_supplied _Chem_comp_db_link.Database_code _Chem_comp_db_link.Accession_code _Chem_comp_db_link.Accession_code_type _Chem_comp_db_link.Entry_mol_code _Chem_comp_db_link.Entry_mol_name _Chem_comp_db_link.Entry_experimental_method _Chem_comp_db_link.Entry_relation_type _Chem_comp_db_link.Entry_details _Chem_comp_db_link.Entry_ID _Chem_comp_db_link.Comp_ID yes USDA_NMR_database 2025 "Compound Number" ? lignin_cw_compound_2025 ? "matching entry" ? bmse010468 1 stop_ loop_ _Chem_comp_citation.Citation_ID _Chem_comp_citation.Citation_label _Chem_comp_citation.Entry_ID _Chem_comp_citation.Comp_ID 1 $citation_1 bmse010468 1 stop_ save_ save_sample_1 _Sample.Sf_category sample _Sample.Sf_framecode sample_1 _Sample.Entry_ID bmse010468 _Sample.ID 1 _Sample.Type solution loop_ _Sample_component.ID _Sample_component.Mol_common_name _Sample_component.Isotopic_labeling _Sample_component.Entity_ID _Sample_component.Entity_label _Sample_component.Product_ID _Sample_component.Type _Sample_component.Concentration_val _Sample_component.Concentration_val_min _Sample_component.Concentration_val_max _Sample_component.Concentration_val_units _Sample_component.Concentration_val_err _Sample_component.Vendor _Sample_component.Vendor_product_name _Sample_component.Vendor_product_code _Sample_component.Entry_ID _Sample_component.Sample_ID 1 "Guaiacylglycerol-A-pinoresinol-B-coniferyl-bis-ether diastereomeric mixture" "natural abundance" 1 $lignin_cw_compound_2025 ? Solute Saturated ? ? 1 ? "John Ralph Lab" "Guaiacylglycerol-A-pinoresinol-B-coniferyl-bis-ether diastereomeric mixture" n/a bmse010468 1 2 Acetone ? 1 ? ? Solvent 100 ? ? % ? ? ? ? bmse010468 1 stop_ save_ save_sample_conditions_1 _Sample_condition_list.Sf_category sample_conditions _Sample_condition_list.Sf_framecode sample_conditions_1 _Sample_condition_list.Entry_ID bmse010468 _Sample_condition_list.ID 1 loop_ _Sample_condition_variable.Type _Sample_condition_variable.Val _Sample_condition_variable.Val_err _Sample_condition_variable.Val_units _Sample_condition_variable.Entry_ID _Sample_condition_variable.Sample_condition_list_ID 1 297 ? K bmse010468 1 stop_ save_ save_software_1 _Software.Sf_category software _Software.Sf_framecode software_1 _Software.Entry_ID bmse010468 _Software.ID 1 _Software.Name X-WINNMR _Software.Version ? _Software.Details ? loop_ _Vendor.Name _Vendor.Address _Vendor.Electronic_address _Vendor.Entry_ID _Vendor.Software_ID Bruker ? ? bmse010468 1 stop_ loop_ _Task.Task _Task.Entry_ID _Task.Software_ID Processing bmse010468 1 stop_ save_ save_Bruker_360 _NMR_spectrometer.Sf_category NMR_spectrometer _NMR_spectrometer.Sf_framecode Bruker_360 _NMR_spectrometer.Entry_ID bmse010468 _NMR_spectrometer.ID 1 _NMR_spectrometer.Manufacturer Bruker _NMR_spectrometer.Model DRX _NMR_spectrometer.Field_strength 360 save_ save_experiment_list _Experiment_list.Sf_category experiment_list _Experiment_list.Sf_framecode experiment_list _Experiment_list.Entry_ID bmse010468 _Experiment_list.ID 1 _Experiment_list.Details ? loop_ _Experiment.ID _Experiment.Name _Experiment.Raw_data_flag _Experiment.NMR_spec_expt_ID _Experiment.NMR_spec_expt_label _Experiment.Sample_ID _Experiment.Sample_label _Experiment.Sample_state _Experiment.Sample_condition_list_ID _Experiment.Sample_condition_list_label _Experiment.NMR_spectrometer_ID _Experiment.NMR_spectrometer_label _Experiment.NMR_spectral_processing_ID _Experiment.NMR_spectral_processing_label _Experiment.Entry_ID _Experiment.Experiment_list_ID 1 "1D 1H" yes ? ? 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_360 ? ? bmse010468 1 2 "1D 13C" yes ? ? 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_360 ? ? bmse010468 1 stop_ save_ save_chem_shift_reference_1 _Chem_shift_reference.Sf_category chem_shift_reference _Chem_shift_reference.Sf_framecode chem_shift_reference_1 _Chem_shift_reference.Entry_ID bmse010468 _Chem_shift_reference.ID 1 _Chem_shift_reference.Details ? loop_ _Chem_shift_ref.Atom_type _Chem_shift_ref.Atom_isotope_number _Chem_shift_ref.Mol_common_name _Chem_shift_ref.Atom_group _Chem_shift_ref.Chem_shift_units _Chem_shift_ref.Chem_shift_val _Chem_shift_ref.Ref_method _Chem_shift_ref.Ref_type _Chem_shift_ref.Indirect_shift_ratio _Chem_shift_ref.External_ref_loc _Chem_shift_ref.External_ref_sample_geometry _Chem_shift_ref.External_ref_axis _Chem_shift_ref.Entry_ID _Chem_shift_ref.Chem_shift_reference_ID H 1 Acetone-d6 "residual solvent methyl proton" ppm 2.04 internal direct 1.000000000 ? ? ? bmse010468 1 C 13 Acetone-d6 "solvent methyl carbon" ppm 29.83 internal direct ? ? ? ? bmse010468 1 stop_ save_ ################################### # Assigned chemical shift lists # ################################### ################################################################### # Chemical Shift Ambiguity Index Value Definitions # # # # Index Value Definition # # # # 1 Unique (geminal atoms and geminal methyl # # groups with identical chemical shifts # # are assumed to be assigned to # # stereospecific atoms) # # 2 Ambiguity of geminal atoms or geminal methyl # # proton groups # # 3 Aromatic atoms on opposite sides of # # symmetrical rings (e.g. Tyr HE1 and HE2 # # protons) # # 4 Intraresidue ambiguities (e.g. Lys HG and # # HD protons or Trp HZ2 and HZ3 protons) # # 5 Interresidue ambiguities (Lys 12 vs. Lys 27) # # 9 Ambiguous, specific ambiguity not defined # # # ################################################################### save_assigned_chemical_shifts_1 _Assigned_chem_shift_list.Sf_category assigned_chemical_shifts _Assigned_chem_shift_list.Sf_framecode assigned_chemical_shifts_1 _Assigned_chem_shift_list.Entry_ID bmse010468 _Assigned_chem_shift_list.ID 1 _Assigned_chem_shift_list.Sample_condition_list_ID 1 _Assigned_chem_shift_list.Sample_condition_list_label $sample_conditions_1 _Assigned_chem_shift_list.Chem_shift_reference_ID 1 _Assigned_chem_shift_list.Chem_shift_reference_label $chem_shift_reference_1 _Assigned_chem_shift_list.Error_derivation_method ? _Assigned_chem_shift_list.Details ? loop_ _Chem_shift_experiment.Experiment_ID _Chem_shift_experiment.Experiment_name _Chem_shift_experiment.Sample_ID _Chem_shift_experiment.Sample_label _Chem_shift_experiment.Entry_ID _Chem_shift_experiment.Assigned_chem_shift_list_ID 1 "1D 1H" 1 $sample_1 bmse010468 1 2 "1D 13C" 1 $sample_1 bmse010468 1 stop_ loop_ _Chem_shift_software.Software_ID _Chem_shift_software.Software_label _Chem_shift_software.Method_ID _Chem_shift_software.Method_label _Chem_shift_software.Entry_ID _Chem_shift_software.Assigned_chem_shift_list_ID 1 $software_1 ? ? bmse010468 1 stop_ loop_ _Atom_chem_shift.ID _Atom_chem_shift.Entity_ID _Atom_chem_shift.Comp_index_ID _Atom_chem_shift.Comp_ID _Atom_chem_shift.Atom_ID _Atom_chem_shift.Atom_type _Atom_chem_shift.Atom_isotope_number _Atom_chem_shift.Val _Atom_chem_shift.Val_err _Atom_chem_shift.Assign_fig_of_merit _Atom_chem_shift.Ambiguity_code _Atom_chem_shift.Occupancy _Atom_chem_shift.Auth_seq_ID _Atom_chem_shift.Auth_comp_ID _Atom_chem_shift.Auth_atom_ID _Atom_chem_shift.Details _Atom_chem_shift.Entry_ID _Atom_chem_shift.Assigned_chem_shift_list_ID 1 1 1 1 C41 C 13 55.15 ? ? 1 ? ? ? DB ? bmse010468 1 2 1 1 1 C42 C 13 55.15 ? ? 1 ? ? ? CB ? bmse010468 1 3 1 1 1 C4 C 13 56.22 ? ? 1 ? ? ? D3OMe ? bmse010468 1 4 1 1 1 C3 C 13 56.25 ? ? 1 ? ? ? A3OMe ? bmse010468 1 5 1 1 1 C5 C 13 56.25 ? ? 1 ? ? ? B3OMe ? bmse010468 1 6 1 1 1 C6 C 13 56.44 ? ? 1 ? ? ? C3OMe ? bmse010468 1 7 1 1 1 C22 C 13 61.82 ? ? 1 ? ? ? G ? bmse010468 1 8 1 1 1 C17 C 13 63.27 ? ? 1 ? ? ? BG ? bmse010468 1 9 1 1 1 C23 C 13 72.23 ? ? 1 ? ? ? DG ? bmse010468 1 10 1 1 1 C24 C 13 72.23 ? ? 1 ? ? ? CG ? bmse010468 1 11 1 1 1 C38 C 13 81.21 ? ? 1 ? ? ? A ? bmse010468 1 12 1 1 1 C37 C 13 85.38 ? ? 1 ? ? ? B ? bmse010468 1 13 1 1 1 C40 C 13 86.37 ? ? 1 ? ? ? CA ? bmse010468 1 14 1 1 1 C39 C 13 86.58 ? ? 1 ? ? ? DA ? bmse010468 1 15 1 1 1 C20 C 13 110.59 ? ? 1 ? ? ? D2 ? bmse010468 1 16 1 1 1 C18 C 13 111.05 ? ? 1 ? ? ? B2 ? bmse010468 1 17 1 1 1 C21 C 13 111.43 ? ? 1 ? ? ? C2 ? bmse010468 1 18 1 1 1 C19 C 13 112.21 ? ? 1 ? ? ? A2 ? bmse010468 1 19 1 1 1 C13 C 13 115.28 ? ? 1 ? ? ? A5 ? bmse010468 1 20 1 1 1 C14 C 13 115.50 ? ? 1 ? ? ? D5 ? bmse010468 1 21 1 1 1 C16 C 13 116.83 ? ? 1 ? ? ? C5 ? bmse010468 1 22 1 1 1 C12 C 13 118.96 ? ? 1 ? ? ? C6 ? bmse010468 1 23 1 1 1 C15 C 13 119.06 ? ? 1 ? ? ? B5 ? bmse010468 1 24 1 1 1 C11 C 13 119.61 ? ? 1 ? ? ? D6 ? bmse010468 1 25 1 1 1 C12 C 13 120.17 ? ? 1 ? ? ? B6 ? bmse010468 1 26 1 1 1 C10 C 13 121.53 ? ? 1 ? ? ? A6 ? bmse010468 1 27 1 1 1 C7 C 13 129.50 ? ? 1 ? ? ? BB ? bmse010468 1 28 1 1 1 C8 C 13 129.88 ? ? 1 ? ? ? BA ? bmse010468 1 29 1 1 1 C26 C 13 130.53 ? ? 1 ? ? ? A1 ? bmse010468 1 30 1 1 1 C25 C 13 132.78 ? ? 1 ? ? ? B1 ? bmse010468 1 31 1 1 1 C27 C 13 134.10 ? ? 1 ? ? ? D1 ? bmse010468 1 32 1 1 1 C28 C 13 136.29 ? ? 1 ? ? ? C1 ? bmse010468 1 33 1 1 1 C30 C 13 146.85 ? ? 1 ? ? ? D4 ? bmse010468 1 34 1 1 1 C29 C 13 147.24 ? ? 1 ? ? ? A4 ? bmse010468 1 35 1 1 1 C32 C 13 147.61 ? ? 1 ? ? ? C4 ? bmse010468 1 36 1 1 1 C33 C 13 148.15 ? ? 1 ? ? ? A3 ? bmse010468 1 37 1 1 1 C34 C 13 148.30 ? ? 1 ? ? ? D3 ? bmse010468 1 38 1 1 1 C36 C 13 151.12 ? ? 1 ? ? ? C3 ? bmse010468 1 39 1 1 1 C35 C 13 151.75 ? ? 1 ? ? ? B3 ? bmse010468 1 40 1 1 1 H96 H 1 5.45 ? ? 1 ? ? ? AA ? bmse010468 1 41 1 1 1 H95 H 1 4.55 ? ? 1 ? ? ? AB ? bmse010468 1 42 1 1 1 H89 H 1 3.82 ? ? 1 ? ? ? AG1 ? bmse010468 1 43 1 1 1 H90 H 1 3.92 ? ? 1 ? ? ? AG2 ? bmse010468 1 44 1 1 1 H98 H 1 4.63 ? ? 1 ? ? ? CA ? bmse010468 1 45 1 1 1 HX H 1 3.04 ? ? 1 ? ? ? CB ? bmse010468 1 46 1 1 1 H93 H 1 3.77 ? ? 1 ? ? ? CG1 ? bmse010468 1 47 1 1 1 H94 H 1 4.17 ? ? 1 ? ? ? CG2 ? bmse010468 1 stop_ save_