data_bmse011806 ####################### # Entry information # ####################### save_entry_information_1 _Entry.Sf_category entry_information _Entry.Sf_framecode entry_information_1 _Entry.ID bmse011806 _Entry.Title N-[(4R)-2,6,6-trimethyl-5,7-dihydro-4H-1-benzofuran-4-yl]acetamide _Entry.Type 'metabolite/natural product' _Entry.Version_type original _Entry.Submission_date 2023-04-05 _Entry.Accession_date 2023-04-05 _Entry.Last_release_date 2023-08-11 _Entry.Original_release_date 2023-08-11 _Entry.Origination author _Entry.NMR_STAR_version 3.2.10.4 _Entry.Experimental_method NMR _Entry.Experimental_method_subtype solution _Entry.DOI 10.12018/bmse011806 loop_ _Entry_experimental_methods.ID _Entry_experimental_methods.Method _Entry_experimental_methods.Subtype _Entry_experimental_methods.Entry_ID 1 NMR solution bmse011806 stop_ loop_ _Entry_author.Ordinal _Entry_author.Given_name _Entry_author.Family_name _Entry_author.First_initial _Entry_author.Entry_ID 1 Sridhar Sreeramulu S. bmse011806 2 Christian Richter C. bmse011806 3 Harald Schwalbe H. bmse011806 4 Hannes Berg . bmse011806 stop_ loop_ _Entry_src.ID _Entry_src.Project_name _Entry_src.Entry_ID 1 EUOS bmse011806 stop_ loop_ _Release.Release_number _Release.Format_type _Release.Format_version _Release.Date _Release.Type _Release.Author _Release.Entry_ID 1 NMR-STAR 3.2.1.18 2023-11-09 original author bmse011806 stop_ loop_ _Auxiliary_files.ID _Auxiliary_files.Name _Auxiliary_files.Format _Auxiliary_files.URI _Auxiliary_files.Details _Auxiliary_files.Entry_ID 1 bmse011806.mol sdf na 'Structure Definition File' bmse011806 stop_ save_ ############### # Citations # ############### save_citations_1 _Citation.Sf_category citations _Citation.Sf_framecode citations_1 _Citation.Entry_ID bmse011806 _Citation.ID 1 _Citation.PubMed_ID 32533387 _Citation.DOI 10.1007/s10858-020-00327-9 _Citation.Title 'NMR quality control of fragment libraries for screening.' _Citation.Status published _Citation.Type journal _Citation.Journal_abbrev 'J Biomol NMR' _Citation.Journal_name_full 'Journal of biomolecular NMR' _Citation.Journal_volume 74 _Citation.Journal_issue 10-11 _Citation.Journal_ISSN 1573-5001 _Citation.Page_first 555 _Citation.Page_last 563 _Citation.Year 2020 loop_ _Citation_author.Ordinal _Citation_author.Given_name _Citation_author.Family_name _Citation_author.First_initial _Citation_author.Entry_ID _Citation_author.Citation_ID 1 Sridhar Sreeramulu S. bmse011806 1 2 Christian Richter C. bmse011806 1 3 Till Kuehn T. bmse011806 1 4 Kamal Azzaoui K. bmse011806 1 5 'Marcel Jules Jose' Blommers . bmse011806 1 6 Rebecca 'Del Conte' R. bmse011806 1 7 Marco Fragai M. bmse011806 1 8 Nils Trieloff N. bmse011806 1 9 Peter Schmieder P. bmse011806 1 10 Marc Nazare M. bmse011806 1 11 Edgar Specker E. bmse011806 1 12 Vladimir Ivanov V. bmse011806 1 13 Hartmut Oschkinat H. bmse011806 1 14 Lucia Banci L. bmse011806 1 15 Harald Schwalbe H. bmse011806 1 stop_ save_ ############################################# # Molecular system (assembly) description # ############################################# save_assembly_1 _Assembly.Sf_category assembly _Assembly.Sf_framecode assembly_1 _Assembly.Entry_ID bmse011806 _Assembly.ID 1 _Assembly.Name N-[(4R)-2,6,6-trimethyl-5,7-dihydro-4H-1-benzofuran-4-yl]acetamide _Assembly.Number_of_components 1 _Assembly.Thiol_state 'not present' loop_ _Entity_assembly.ID _Entity_assembly.Entity_assembly_name _Entity_assembly.Entity_ID _Entity_assembly.Experimental_data_reported _Entity_assembly.Physical_state _Entity_assembly.Conformational_isomer _Entity_assembly.Chemical_exchange_state _Entity_assembly.Entry_ID _Entity_assembly.Assembly_ID 1 chem_comp_1 1 yes native no no bmse011806 1 stop_ loop_ _Atom.Assembly_atom_ID _Atom.Entity_assembly_ID _Atom.Entity_ID _Atom.Comp_index_ID _Atom.Seq_ID _Atom.Atom_ID _Atom.Type_symbol _Atom.Entry_ID _Atom.Assembly_ID 1 1 1 1 1 C1 C bmse011806 1 2 1 1 1 1 C2 C bmse011806 1 3 1 1 1 1 C3 C bmse011806 1 4 1 1 1 1 C4 C bmse011806 1 5 1 1 1 1 C5 C bmse011806 1 6 1 1 1 1 C6 C bmse011806 1 7 1 1 1 1 C7 C bmse011806 1 8 1 1 1 1 C8 C bmse011806 1 9 1 1 1 1 C9 C bmse011806 1 10 1 1 1 1 C10 C bmse011806 1 11 1 1 1 1 C11 C bmse011806 1 12 1 1 1 1 C12 C bmse011806 1 13 1 1 1 1 C13 C bmse011806 1 14 1 1 1 1 N14 N bmse011806 1 15 1 1 1 1 O15 O bmse011806 1 16 1 1 1 1 O16 O bmse011806 1 stop_ save_ #################################### # Biological polymers and ligands # #################################### save_entity_1 _Entity.Sf_category entity _Entity.Sf_framecode entity_1 _Entity.Entry_ID bmse011806 _Entity.ID 1 _Entity.Name N-[(4R)-2,6,6-trimethyl-5,7-dihydro-4H-1-benzofuran-4-yl]acetamide _Entity.Type non-polymer _Entity.Ambiguous_conformational_states no _Entity.Ambiguous_chem_comp_sites no _Entity.Nstd_linkage no _Entity.Nonpolymer_comp_label chem_comp_1 _Entity.Number_of_monomers 1 _Entity.Number_of_nonpolymer_components 1 _Entity.Thiol_state 'not present' _Entity.Formula_weight 221.29546 loop_ _Entity_comp_index.ID _Entity_comp_index.Auth_seq_ID _Entity_comp_index.Comp_label _Entity_comp_index.Entry_ID _Entity_comp_index.Entity_ID 1 1 chem_comp_1 bmse011806 1 stop_ save_ ################################# # Polymer residues and ligands # ################################# save_chem_comp_1 _Chem_comp.Sf_category chem_comp _Chem_comp.Sf_framecode chem_comp_1 _Chem_comp.Entry_ID bmse011806 _Chem_comp.Name N-[(4R)-2,6,6-trimethyl-5,7-dihydro-4H-1-benzofuran-4-yl]acetamide _Chem_comp.Number_atoms_all 16 _Chem_comp.InChI_code InChI=1S/C13H19NO2/c1-8-5-10-11(14-9(2)15)6-13(3,4)7-12(10)16-8/h5,11H,6-7H2,1-4H3,(H,14,15)/t11-/m1/s1 _Chem_comp.Formal_charge 0 _Chem_comp.Aromatic yes _Chem_comp.Formula C13H19NO2 _Chem_comp.Formula_weight 221.29546 _Chem_comp.Formula_mono_iso_wt_nat 221.141578853 _Chem_comp.Formula_mono_iso_wt_13C 234.18519174700006 _Chem_comp.Formula_mono_iso_wt_15N 222.138613746 _Chem_comp.Formula_mono_iso_wt_13C_15N 235.18222664000007 _Chem_comp.Image_file_name bmse011806.png _Chem_comp.Image_file_format png _Chem_comp.Struct_file_name bmse011806.sdf _Chem_comp.Struct_file_format sdf loop_ _Chem_comp_descriptor.Descriptor _Chem_comp_descriptor.Type _Chem_comp_descriptor.Program _Chem_comp_descriptor.Program_version _Chem_comp_descriptor.Entry_ID CC(=O)N[C@@H]1CC(C)(C)Cc2oc(C)cc21 SMILES_CANONICAL RDKit 2022.03.5 bmse011806 CC(=O)N[C@@H]1CC(C)(C)Cc2oc(C)cc21 SMILES_ISOMERIC RDKit 2022.03.5 bmse011806 CC(=O)N[C@@H]1CC(C)(C)Cc2oc(C)cc21 SMILES RDKit 2022.03.5 bmse011806 CC(=O)N[C@@H]1CC(C)(C)Cc2c1cc(o2)C SMILES_CANONICAL OpenBabel 3.1.0 bmse011806 CC(=O)N[C@@H]1CC(C)(C)Cc2c1cc(o2)C SMILES OpenBabel 3.1.0 bmse011806 InChI=1S/C13H19NO2/c1-8-5-10-11(14-9(2)15)6-13(3,4)7-12(10)16-8/h5,11H,6-7H2,1-4H3,(H,14,15)/t11-/m1/s1 InChI OpenBabel 3.1.0 bmse011806 YUVNCBVOTWCVFT-LLVKDONJSA-N InChI_KEY OpenBabel 3.1.0 bmse011806 InChI=1S/C13H19NO2/c1-8-5-10-11(14-9(2)15)6-13(3,4)7-12(10)16-8/h5,11H,6-7H2,1-4H3,(H,14,15)/t11-/m1/s1 InChI ALATIS na bmse011806 stop_ loop_ _Chem_comp_atom.Atom_ID _Chem_comp_atom.Type_symbol _Chem_comp_atom.Stereo_config _Chem_comp_atom.Charge _Chem_comp_atom.Aromatic_flag _Chem_comp_atom.PDBX_ordinal _Chem_comp_atom.Entry_ID C1 C N 0 no 1 bmse011806 C2 C N 0 no 2 bmse011806 C3 C N 0 no 3 bmse011806 C4 C N 0 no 4 bmse011806 C5 C N 0 yes 5 bmse011806 C6 C N 0 no 6 bmse011806 C7 C N 0 no 7 bmse011806 C8 C N 0 yes 8 bmse011806 C9 C N 0 no 9 bmse011806 C10 C N 0 yes 10 bmse011806 C11 C R 0 no 11 bmse011806 C12 C N 0 yes 12 bmse011806 C13 C N 0 no 13 bmse011806 N14 N N 0 no 14 bmse011806 O15 O N 0 no 15 bmse011806 O16 O N 0 yes 16 bmse011806 stop_ loop_ _Atom_nomenclature.Atom_ID _Atom_nomenclature.Atom_name _Atom_nomenclature.Naming_system _Atom_nomenclature.Entry_ID C13 C1 ALATIS bmse011806 C16 C2 ALATIS bmse011806 C14 C3 ALATIS bmse011806 C15 C4 ALATIS bmse011806 C5 C5 ALATIS bmse011806 C11 C6 ALATIS bmse011806 C8 C7 ALATIS bmse011806 C6 C8 ALATIS bmse011806 C10 C9 ALATIS bmse011806 C1 C10 ALATIS bmse011806 C3 C11 ALATIS bmse011806 C2 C12 ALATIS bmse011806 C9 C13 ALATIS bmse011806 N7 N14 ALATIS bmse011806 O12 O15 ALATIS bmse011806 O4 O16 ALATIS bmse011806 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.Aromatic_flag _Chem_comp_bond.Stereo_config _Chem_comp_bond.Ordinal _Chem_comp_bond.Entry_ID 1 covalent AROM C5 C8 yes N 1 bmse011806 2 covalent SING C7 C13 no N 2 bmse011806 3 covalent SING C8 C1 no N 3 bmse011806 4 covalent SING C9 C2 no N 4 bmse011806 5 carbonyl DOUB C9 O15 no N 5 bmse011806 6 covalent AROM C10 C5 yes N 6 bmse011806 7 covalent SING C10 C11 no N 7 bmse011806 8 covalent AROM C10 C12 yes N 8 bmse011806 9 covalent SING C11 C6 no N 9 bmse011806 10 covalent SING C11 N14 no N 10 bmse011806 11 covalent SING C12 C7 no N 11 bmse011806 12 covalent AROM C12 O16 yes N 12 bmse011806 13 covalent SING C13 C3 no N 13 bmse011806 14 covalent SING C13 C4 no N 14 bmse011806 15 covalent SING C13 C6 no N 15 bmse011806 16 amide SING N14 C9 no N 16 bmse011806 17 covalent AROM O16 C8 yes N 17 bmse011806 stop_ loop_ _Chem_comp_db_link.Database_code _Chem_comp_db_link.Accession_code _Chem_comp_db_link.Accession_code_type _Chem_comp_db_link.Entry_ID EU-OPENSCREEN EOS102506 'compound ID' bmse011806 stop_ save_ ##################################### # Sample contents and methodology # ##################################### ######################## # Sample description # ######################## save_sample_1 _Sample.Sf_category sample _Sample.Sf_framecode sample_1 _Sample.Entry_ID bmse011806 _Sample.ID 1 _Sample.Name 'sample 1' _Sample.Type solution _Sample.Aggregate_sample_number 1 loop_ _Sample_component.ID _Sample_component.Mol_common_name _Sample_component.Isotopic_labeling _Sample_component.Assembly_ID _Sample_component.Assembly_label _Sample_component.Entity_ID _Sample_component.Entity_label _Sample_component.Type _Sample_component.Concentration_val _Sample_component.Concentration_val_units _Sample_component.Entry_ID _Sample_component.Sample_ID 1 N-[(4R)-2,6,6-trimethyl-5,7-dihydro-4H-1-benzofuran-4-yl]acetamide 'natural abundance' 1 $assembly_1 1 $entity_1 solute 2 mM bmse011806 1 2 'Sodium phosphate' 'natural abundance' . . . . buffer 25 mM bmse011806 1 3 'Sodium chloride' 'natural abundance' . . . . salt 150 mM bmse011806 1 4 DSS 'natural abundance' . . . . reference 10 uM bmse011806 1 5 H2O 'natural abundance' . . . . solvent 95 % bmse011806 1 6 DMSO '[2H U-100%]' . . . . solvent 5 % bmse011806 1 stop_ save_ ####################### # Sample conditions # ####################### save_sample_conditions_1 _Sample_condition_list.Sf_category sample_conditions _Sample_condition_list.Sf_framecode sample_conditions_1 _Sample_condition_list.Entry_ID bmse011806 _Sample_condition_list.ID 1 _Sample_condition_list.Name 'sample conditions 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 pH 7.5 . pH bmse011806 1 pressure 1 . atm bmse011806 1 temperature 298 0.1 K bmse011806 1 stop_ save_ ############################ # Computer software used # ############################ save_software_1 _Software.Sf_category software _Software.Sf_framecode software_1 _Software.Entry_ID bmse011806 _Software.ID 1 _Software.Name TopSpin _Software.Version 4.0.3 loop_ _Vendor.Name _Vendor.Electronic_address _Vendor.Entry_ID _Vendor.Software_ID 'Bruker Biospin' http://www.bruker.com/products/mr/nmr/nmr-software/software/topspin/ bmse011806 1 stop_ loop_ _Task.Task _Task.Entry_ID _Task.Software_ID 'data analysis' bmse011806 1 'peak picking' bmse011806 1 processing bmse011806 1 stop_ save_ ######################### # Experimental detail # ######################### ################################## # NMR Spectrometer definitions # ################################## save_NMR_spectrometer_1 _NMR_spectrometer.Sf_category NMR_spectrometer _NMR_spectrometer.Sf_framecode NMR_spectrometer_1 _NMR_spectrometer.Entry_ID bmse011806 _NMR_spectrometer.ID 1 _NMR_spectrometer.Name 'spectrometer Bruker' _NMR_spectrometer.Manufacturer Bruker _NMR_spectrometer.Model Avance _NMR_spectrometer.Field_strength 600 save_ ############################# # NMR applied experiments # ############################# save_experiment_list_1 _Experiment_list.Sf_category experiment_list _Experiment_list.Sf_framecode experiment_list_1 _Experiment_list.Entry_ID bmse011806 _Experiment_list.ID 1 loop_ _Experiment.ID _Experiment.Name _Experiment.Raw_data_flag _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.Entry_ID _Experiment.Experiment_list_ID 1 '1D 1H' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $NMR_spectrometer_1 bmse011806 1 stop_ loop_ _Experiment_file.Experiment_ID _Experiment_file.Name _Experiment_file.Type _Experiment_file.Content _Experiment_file.Directory_path _Experiment_file.Entry_ID _Experiment_file.Experiment_list_ID 1 1 text/directory 'NMR experiment directory' nmr/set01/ bmse011806 1 1 cmcproject.xml text/xml 'spectrum analysis' nmr/set01/1/pdata/1/ bmse011806 1 1 multiplet.txt text 'Peak list' nmr/set01/1/pdata/1/ bmse011806 1 1 spectrum_overview.pdf pdf 'Spectrum image' nmr/set01/1/pdata/1/ bmse011806 1 1 spectrum_overview.png image/png 'Spectral image' nmr/set01/1/pdata/1/ bmse011806 1 stop_ save_ #################### # NMR parameters # #################### ############################## # Assigned chemical shifts # ############################## ################################ # Chemical shift referencing # ################################ 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 bmse011806 _Chem_shift_reference.ID 1 _Chem_shift_reference.Name 'chem shift ref set' 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.Entry_ID _Chem_shift_ref.Chem_shift_reference_ID H 1 DSS 'methyl protons' ppm 0.0 internal direct 1.0 bmse011806 1 stop_ save_ ######################### # Spectral peak lists # ######################### save_spectral_peak_list_1 _Spectral_peak_list.Sf_category spectral_peak_list _Spectral_peak_list.Sf_framecode spectral_peak_list_1 _Spectral_peak_list.Entry_ID bmse011806 _Spectral_peak_list.ID 1 _Spectral_peak_list.Name 'spectral peaks 1D 1H' _Spectral_peak_list.Sample_ID 1 _Spectral_peak_list.Sample_label $sample_1 _Spectral_peak_list.Sample_condition_list_ID 1 _Spectral_peak_list.Sample_condition_list_label $sample_conditions_1 _Spectral_peak_list.Chem_shift_reference_ID 1 _Spectral_peak_list.Experiment_ID 1 _Spectral_peak_list.Experiment_name '1D 1H' _Spectral_peak_list.Number_of_spectral_dimensions 1 _Spectral_peak_list.Assigned_chem_shift_list_ID 1 _Spectral_peak_list.Details 'F1: 1H' loop_ _Spectral_dim.ID _Spectral_dim.Spectrometer_frequency _Spectral_dim.Atom_type _Spectral_dim.Atom_isotope_number _Spectral_dim.Spectral_region _Spectral_dim.Sweep_width _Spectral_dim.Sweep_width_units _Spectral_dim.Entry_ID _Spectral_dim.Spectral_peak_list_ID 1 600.1728185 H 1 'Full H' 12.0157698570257 ppm bmse011806 1 stop_ loop_ _Spectral_peak_software.Software_ID _Spectral_peak_software.Software_label _Spectral_peak_software.Entry_ID _Spectral_peak_software.Spectral_peak_list_ID 1 $software_1 bmse011806 1 stop_ loop_ _Peak.ID _Peak.Entry_ID _Peak.Spectral_peak_list_ID 1 bmse011806 1 2 bmse011806 1 3 bmse011806 1 4 bmse011806 1 5 bmse011806 1 6 bmse011806 1 7 bmse011806 1 8 bmse011806 1 9 bmse011806 1 10 bmse011806 1 11 bmse011806 1 12 bmse011806 1 stop_ loop_ _Peak_char.Peak_ID _Peak_char.Spectral_dim_ID _Peak_char.Chem_shift_val _Peak_char.Details _Peak_char.Entry_ID _Peak_char.Spectral_peak_list_ID 1 1 1.6527 7_dd_Q2 bmse011806 1 2 1 4.6544 SUP bmse011806 1 3 1 0.8484 15_s bmse011806 1 4 1 1.8966 16_d_Q3 bmse011806 1 5 1 0.9746 14_s bmse011806 1 6 1 2.3006 12_d bmse011806 1 7 1 2.1958 12_d bmse011806 1 8 1 0.0374 TMS bmse011806 1 9 1 1.2744 7_m_Q1 bmse011806 1 10 1 2.1097 4_s bmse011806 1 11 1 2.5703 DMSO bmse011806 1 12 1 5.8433 9_s bmse011806 1 stop_ loop_ _Spectral_transition.ID _Spectral_transition.Entry_ID _Spectral_transition.Spectral_peak_list_ID 1 bmse011806 1 2 bmse011806 1 3 bmse011806 1 4 bmse011806 1 5 bmse011806 1 6 bmse011806 1 7 bmse011806 1 8 bmse011806 1 9 bmse011806 1 10 bmse011806 1 11 bmse011806 1 12 bmse011806 1 13 bmse011806 1 14 bmse011806 1 15 bmse011806 1 16 bmse011806 1 17 bmse011806 1 18 bmse011806 1 19 bmse011806 1 20 bmse011806 1 21 bmse011806 1 22 bmse011806 1 stop_ loop_ _Spectral_transition_char.Spectral_transition_ID _Spectral_transition_char.Spectral_dim_ID _Spectral_transition_char.Chem_shift_val _Spectral_transition_char.Entry_ID _Spectral_transition_char.Spectral_peak_list_ID 1 1 1.6687 bmse011806 1 2 1 1.6597 bmse011806 1 3 1 1.6460 bmse011806 1 4 1 1.6367 bmse011806 1 5 1 4.6544 bmse011806 1 6 1 0.8484 bmse011806 1 7 1 1.8979 bmse011806 1 8 1 1.8954 bmse011806 1 9 1 0.9746 bmse011806 1 10 1 2.2870 bmse011806 1 11 1 2.3141 bmse011806 1 12 1 2.1821 bmse011806 1 13 1 2.2095 bmse011806 1 14 1 0.0374 bmse011806 1 15 1 1.2947 bmse011806 1 16 1 1.2784 bmse011806 1 17 1 1.2735 bmse011806 1 18 1 1.2541 bmse011806 1 19 1 2.1097 bmse011806 1 20 1 2.5690 bmse011806 1 21 1 2.5717 bmse011806 1 22 1 5.8433 bmse011806 1 stop_ loop_ _Peak_coupling.ID _Peak_coupling.Peak_ID _Peak_coupling.Spectral_dim_ID _Peak_coupling.Coupling_val _Peak_coupling.Entry_ID _Peak_coupling.Spectral_peak_list_ID 1 1 1 5.5020 bmse011806 1 2 2 1 0.0000 bmse011806 1 3 3 1 0.0000 bmse011806 1 4 4 1 0.0000 bmse011806 1 5 5 1 0.0000 bmse011806 1 6 6 1 16.2858 bmse011806 1 7 7 1 16.4325 bmse011806 1 8 8 1 0.0000 bmse011806 1 9 9 1 8.1185 bmse011806 1 10 10 1 0.0000 bmse011806 1 11 11 1 1.6139 bmse011806 1 12 12 1 0.0000 bmse011806 1 stop_ save_