data_bmse000761 ####################### # Entry information # ####################### save_entry_information _Entry.Sf_category entry_information _Entry.Sf_framecode entry_information _Entry.ID bmse000761 _Entry.Title mesaconic_acid _Entry.Version_type original _Entry.Submission_date 2010-07-19 _Entry.Accession_date 2010-07-19 _Entry.Last_release_date 2010-07-19 _Entry.Original_release_date 2010-07-19 _Entry.Origination author _Entry.NMR_STAR_version 'NMR STAR v3.1' _Entry.Original_NMR_STAR_version 'NMR STAR v3.1' _Entry.Experimental_method NMR _Entry.Experimental_method_subtype solution _Entry.DOI 10.13018/BMSE000761 _Entry.BMRB_internal_directory_name mesaconic_acid loop_ _Entry_author.Ordinal _Entry_author.Given_name _Entry_author.Family_name _Entry_author.Middle_initials _Entry_author.Entry_ID 1 Francisca Jofre ? bmse000761 2 Mark Anderson E. bmse000761 3 John Markley L. bmse000761 4 Ravi Rapolu ? bmse000761 stop_ loop_ _Entry_src.Project_name _Entry_src.Organization_full_name _Entry_src.Organization_initials _Entry_src.Entry_ID metabolomics 'Madison Metabolomics Consortium' MMC bmse000761 stop_ loop_ _Data_set.Entry_ID bmse000761 stop_ loop_ _Datum.Entry_ID bmse000761 stop_ loop_ _Release.Release_number _Release.Format_type _Release.Format_version _Release.Date _Release.Submission_date _Release.Type _Release.Author _Release.Detail _Release.Entry_ID 1 . . 2010-07-19 2010-07-19 original BMRB 'Original spectra from MMC' bmse000761 2 . . 2017-10-12 2017-10-12 update BMRB 'Remediated Experiment_file loop if present and standardized mol and png file tags.' bmse000761 3 . . 2017-12-19 2017-10-12 update BMRB 'InChI numbering updated according to ALATIS' bmse000761 stop_ save_ ############### # Citations # ############### save_citation_1 _Citation.Sf_category citations _Citation.Sf_framecode citation_1 _Citation.Entry_ID bmse000761 _Citation.ID 1 _Citation.Class 'reference citation' _Citation.PubMed_ID 17170002 _Citation.Title ; Database resources of the National Center for Biotechnology Information. ; _Citation.Status published _Citation.Type internet _Citation.WWW_URL http://pubchem.ncbi.nlm.nih.gov/ _Citation.Year 2006 loop_ _Citation_author.Ordinal _Citation_author.Given_name _Citation_author.Family_name _Citation_author.First_initial _Citation_author.Middle_initials _Citation_author.Entry_ID _Citation_author.Citation_ID 1 D. Wheeler D. L. bmse000761 1 2 T. Barrett T. ? bmse000761 1 3 D. Benson D. A. bmse000761 1 4 S. Bryant S. H. bmse000761 1 5 K. Canese K. ? bmse000761 1 6 V. Chetvenin V. ? bmse000761 1 7 D. Church D. M. bmse000761 1 8 M. DiCuccio M. ? bmse000761 1 9 R. Edgar R. ? bmse000761 1 10 S. Federhen S. ? bmse000761 1 11 L. Geer L. Y. bmse000761 1 12 W. Helmberg W. ? bmse000761 1 13 Y. Kapustin Y. ? bmse000761 1 14 D. Kenton D. L. bmse000761 1 15 O. Khovayko O. ? bmse000761 1 16 D. Lipman D. J. bmse000761 1 17 T. Madden T. L. bmse000761 1 18 D. Maglott D. R. bmse000761 1 19 J. Ostell J. ? bmse000761 1 20 K. Pruitt K. D. bmse000761 1 21 G. Schuler G. D. bmse000761 1 22 L. Schriml L. M. bmse000761 1 23 E. Sequeira E. ? bmse000761 1 24 S. Sherry S. T. bmse000761 1 25 K. Sirotkin K. ? bmse000761 1 26 A. Souvorov A. ? bmse000761 1 27 G. Starchenko G. ? bmse000761 1 28 T. Suzek T. O. bmse000761 1 29 R. Tatusov R. ? bmse000761 1 30 T. Tatusova T. A. bmse000761 1 31 L. Bagner L. ? bmse000761 1 32 E. Yaschenko E. ? bmse000761 1 stop_ save_ ############################################# # Molecular system (assembly) description # ############################################# save_assembly _Assembly.Sf_category assembly _Assembly.Sf_framecode assembly _Assembly.Entry_ID bmse000761 _Assembly.ID 1 _Assembly.Name Mesaconic _Assembly.Number_of_components 1 _Assembly.Organic_ligands 0 _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.Entry_ID _Entity_assembly.Assembly_ID 1 'Mesaconic acid' 1 $Mesaconic-acid yes native no no bmse000761 1 stop_ save_ #################################### # Biological polymers and ligands # #################################### save_Mesaconic-acid _Entity.Sf_category entity _Entity.Sf_framecode Mesaconic-acid _Entity.Entry_ID bmse000761 _Entity.ID 1 _Entity.Name 'Mesaconic acid' _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 bmse000761 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 bmse000761 _Chem_comp.ID 1 _Chem_comp.Name 'Mesaconic acid' _Chem_comp.Type non-polymer _Chem_comp.BMRB_code bmse000761 _Chem_comp.InChI_code InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ _Chem_comp.Formula 'C5 H6 O4' _Chem_comp.Formula_weight 130.09874 _Chem_comp.Formula_mono_iso_wt_nat 130.026608681 _Chem_comp.Formula_mono_iso_wt_13C 135.04338287 _Chem_comp.Formula_mono_iso_wt_15N 130.026608681 _Chem_comp.Formula_mono_iso_wt_13C_15N 135.04338287 _Chem_comp.Image_file_name bmse000761.png _Chem_comp.Image_file_format png _Chem_comp.Struct_file_name bmse000761.mol _Chem_comp.Struct_file_format mol loop_ _Chem_comp_common_name.Name _Chem_comp_common_name.Type _Chem_comp_common_name.Entry_ID _Chem_comp_common_name.Comp_ID 'Kyselina mesakonova' synonym bmse000761 1 '2-Butenedioic acid, 2-methyl-, (2E)-' synonym bmse000761 1 'trans-2-Methyl-2-butenedioic acid' synonym bmse000761 1 2-Methylfumarate synonym bmse000761 1 'Fumaric acid, methyl-' synonym bmse000761 1 '2-Butenedioic acid, 2-methyl-, (E)- (9CI)' synonym bmse000761 1 'Mesaconic acid' synonym bmse000761 1 'trans-1-Propene-1,2-dicarboxylic acid' synonym bmse000761 1 '2-Butenedioic acid, 2-methyl-, (E)-' synonym bmse000761 1 'Kyselina mesakonova [Czech]' synonym bmse000761 1 'Citraconic acid' synonym bmse000761 1 Mesaconate synonym bmse000761 1 'Butenedioic acid, methyl-, (E)-' synonym bmse000761 1 'Methylfumaric acid' synonym bmse000761 1 '2-Methylfumaric acid' synonym bmse000761 1 stop_ loop_ _Chem_comp_descriptor.Descriptor _Chem_comp_descriptor.Type _Chem_comp_descriptor.Program _Chem_comp_descriptor.Program_version _Chem_comp_descriptor.Entry_ID _Chem_comp_descriptor.Comp_ID ; InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ ; INCHI na na bmse000761 1 InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ INCHI ALATIS 3.003 bmse000761 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 '(E)-2-methylbut-2-enedioic acid' PUBCHEM_IUPAC_NAME bmse000761 1 'mesaconic acid' PUBCHEM_IUPAC_TRADITIONAL_NAME bmse000761 1 '(E)-2-methylbut-2-enedioic acid' PUBCHEM_IUPAC_OPENEYE_NAME bmse000761 1 '(E)-2-methyl-2-butenedioic acid' PUBCHEM_IUPAC_CAS_NAME bmse000761 1 '(E)-2-methylbut-2-enedioic acid' PUBCHEM_IUPAC_SYSTEMATIC_NAME bmse000761 1 stop_ loop_ _Chem_comp_SMILES.Type _Chem_comp_SMILES.String _Chem_comp_SMILES.Entry_ID _Chem_comp_SMILES.Comp_ID Canonical CC(=CC(=O)O)C(=O)O bmse000761 1 Isomeric C/C(=C\C(=O)O)/C(=O)O bmse000761 1 stop_ loop_ _Chem_comp_atom.Atom_ID _Chem_comp_atom.Type_symbol _Chem_comp_atom.Drawing_2D_coord_x _Chem_comp_atom.Drawing_2D_coord_y _Chem_comp_atom.PDBX_ordinal _Chem_comp_atom.Entry_ID _Chem_comp_atom.Comp_ID O8 O 2.5369 -0.2500 1 bmse000761 1 O6 O 6.8671 0.2500 2 bmse000761 1 O9 O 3.4030 1.2500 3 bmse000761 1 O7 O 6.0010 -1.2500 4 bmse000761 1 C3 C 4.2690 -0.2500 5 bmse000761 1 C1 C 4.2690 -1.2500 6 bmse000761 1 C2 C 5.1350 0.2500 7 bmse000761 1 C5 C 3.4030 0.2500 8 bmse000761 1 C4 C 6.0010 -0.2500 9 bmse000761 1 H10 H 3.6490 -1.2500 10 bmse000761 1 H11 H 4.2690 -1.8700 11 bmse000761 1 H12 H 4.8890 -1.2500 12 bmse000761 1 H13 H 5.1350 0.8700 13 bmse000761 1 H15 H 2.0000 0.0600 14 bmse000761 1 H14 H 7.4040 -0.0600 15 bmse000761 1 stop_ loop_ _Atom_nomenclature.Atom_ID _Atom_nomenclature.Atom_name _Atom_nomenclature.Naming_system _Atom_nomenclature.Entry_ID _Atom_nomenclature.Comp_ID O8 O1 BMRB bmse000761 1 O6 O2 BMRB bmse000761 1 O9 O3 BMRB bmse000761 1 O7 O4 BMRB bmse000761 1 C3 C5 BMRB bmse000761 1 C1 C6 BMRB bmse000761 1 C2 C7 BMRB bmse000761 1 C5 C8 BMRB bmse000761 1 C4 C9 BMRB bmse000761 1 H10 H10 BMRB bmse000761 1 H11 H11 BMRB bmse000761 1 H12 H12 BMRB bmse000761 1 H13 H13 BMRB bmse000761 1 H15 H14 BMRB bmse000761 1 H14 H15 BMRB bmse000761 1 O8 O8 ALATIS bmse000761 1 O6 O6 ALATIS bmse000761 1 O9 O9 ALATIS bmse000761 1 O7 O7 ALATIS bmse000761 1 C3 C3 ALATIS bmse000761 1 C1 C1 ALATIS bmse000761 1 C2 C2 ALATIS bmse000761 1 C5 C5 ALATIS bmse000761 1 C4 C4 ALATIS bmse000761 1 H10 H10 ALATIS bmse000761 1 H11 H11 ALATIS bmse000761 1 H12 H12 ALATIS bmse000761 1 H13 H13 ALATIS bmse000761 1 H15 H15 ALATIS bmse000761 1 H14 H14 ALATIS bmse000761 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.Entry_ID _Chem_comp_bond.Comp_ID 1 covalent SING O8 C5 bmse000761 1 2 covalent SING O8 H15 bmse000761 1 3 covalent SING O6 C4 bmse000761 1 4 covalent SING O6 H14 bmse000761 1 5 covalent DOUB O9 C5 bmse000761 1 6 covalent DOUB O7 C4 bmse000761 1 7 covalent SING C3 C1 bmse000761 1 8 covalent DOUB C3 C2 bmse000761 1 9 covalent SING C3 C5 bmse000761 1 10 covalent SING C1 H10 bmse000761 1 11 covalent SING C1 H11 bmse000761 1 12 covalent SING C1 H12 bmse000761 1 13 covalent SING C2 C4 bmse000761 1 14 covalent SING C2 H13 bmse000761 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_name _Chem_comp_db_link.Entry_relation_type _Chem_comp_db_link.Entry_ID _Chem_comp_db_link.Comp_ID yes PubChem 638129 cid 'Mesaconic acid' 'matching entry' bmse000761 1 yes CAS 498-24-8 ? 'Mesaconic acid' 'matching entry' bmse000761 1 yes PubChem 153625 sid 'Mesaconic acid' 'matching entry' bmse000761 1 yes MMCD cq_01113 ? 'Mesaconic acid' 'matching entry' bmse000761 1 no PubChem 4868 sid 'Mesaconic acid' 'matching entry' bmse000761 1 no PubChem 10524186 sid 'Mesaconic acid' 'matching entry' bmse000761 1 no PubChem 8138148 sid 'Mesaconic acid' 'matching entry' bmse000761 1 no PubChem 10390688 sid 'Mesaconic acid' 'matching entry' bmse000761 1 no 'CAS Registry' 498-24-8 'registry number' 'Mesaconic acid' 'matching entry' bmse000761 1 no ChemIDplus 000498248 ? 'Mesaconic acid' 'matching entry' bmse000761 1 no MTDP NSC32949 ? 'Mesaconic acid' 'matching entry' bmse000761 1 no EINECS 207-859-2 ? 'Mesaconic acid' 'matching entry' bmse000761 1 no KEGG C01732 'compound ID' 'Mesaconic acid' 'matching entry' bmse000761 1 no 'Beilstein Handbook Reference' 4-02-00-02231 ? 'Mesaconic acid' 'matching entry' bmse000761 1 no 'NIST Chemistry WebBook' 1473579925 ? 'Mesaconic acid' 'matching entry' bmse000761 1 no NIST 1473579925 ? 'Mesaconic acid' 'matching entry' bmse000761 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 bmse000761 1 stop_ save_ ##################################### # Sample contents and methodology # ##################################### ######################## # Sample description # ######################## save_sample_1 _Sample.Sf_category sample _Sample.Sf_framecode sample_1 _Sample.Entry_ID bmse000761 _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.Type _Sample_component.Concentration_val _Sample_component.Concentration_val_units _Sample_component.Vendor _Sample_component.Vendor_product_name _Sample_component.Entry_ID _Sample_component.Sample_ID 1 'Mesaconic acid' 'natural abundance' 1 $Mesaconic-acid Solute 100 mM sigma/aldrich 'Mesaconic acid' bmse000761 1 2 D2O ? ? ? Solvent 100 % ? ? bmse000761 1 3 'sodium phosphate' ? ? ? Buffer 50 mM ? ? bmse000761 1 4 'sodium azide' ? ? ? Cytocide 500 uM ? ? bmse000761 1 5 DSS ? ? ? Reference 500 uM ? ? bmse000761 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 bmse000761 _Sample_condition_list.ID 1 loop_ _Sample_condition_variable.Type _Sample_condition_variable.Val _Sample_condition_variable.Val_units _Sample_condition_variable.Entry_ID _Sample_condition_variable.Sample_condition_list_ID pH 7.4 pH bmse000761 1 temperature 298 K bmse000761 1 stop_ save_ ############################ # Computer software used # ############################ save_software_1 _Software.Sf_category software _Software.Sf_framecode software_1 _Software.Entry_ID bmse000761 _Software.ID 1 _Software.Name TopSpin _Software.Version 2.1 loop_ _Vendor.Name _Vendor.Entry_ID _Vendor.Software_ID 'Bruker Biospin' bmse000761 1 stop_ loop_ _Task.Task _Task.Entry_ID _Task.Software_ID Collection bmse000761 1 Processing bmse000761 1 'Data analysis' bmse000761 1 'Peak picking' bmse000761 1 stop_ save_ ######################### # Experimental detail # ######################### ################################## # NMR Spectrometer definitions # ################################## save_Bruker_DMX_500 _NMR_spectrometer.Sf_category NMR_spectrometer _NMR_spectrometer.Sf_framecode Bruker_DMX_500 _NMR_spectrometer.Entry_ID bmse000761 _NMR_spectrometer.ID 1 _NMR_spectrometer.Manufacturer Bruker _NMR_spectrometer.Model DMX _NMR_spectrometer.Field_strength 500 save_ ############################# # NMR applied experiments # ############################# save_experiment_list _Experiment_list.Sf_category experiment_list _Experiment_list.Sf_framecode experiment_list _Experiment_list.Entry_ID bmse000761 _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 $Bruker_DMX_500 bmse000761 1 2 '2D [1H,1H]-TOCSY' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_DMX_500 bmse000761 1 3 '1D 13C' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_DMX_500 bmse000761 1 4 '1D DEPT90' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_DMX_500 bmse000761 1 5 '1D DEPT135' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_DMX_500 bmse000761 1 6 '2D [1H,13C]-HSQC' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_DMX_500 bmse000761 1 7 '2D [1H,13C]-HMBC' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_DMX_500 bmse000761 1 8 '2D [1H,1H]-COSY' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $Bruker_DMX_500 bmse000761 1 stop_ loop_ _Experiment_file.Experiment_ID _Experiment_file.Name _Experiment_file.Type _Experiment_file.Directory_path _Experiment_file.Details _Experiment_file.Entry_ID _Experiment_file.Experiment_list_ID 1 1H text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 1 1H.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 2 HH_TOCSY text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 2 HH_TOCSY.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 3 13C text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 3 13C.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 4 DEPT_90 text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 4 DEPT_90.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 5 DEPT_135 text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 5 DEPT_135.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 6 1H_13C_HSQC text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 6 1H_13C_HSQC.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 7 1H_13C_HMBC text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 7 1H_13C_HMBC.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 8 HH_COSY text/directory nmr/set01/ 'NMR experiment directory' bmse000761 1 8 HH_COSY.png image/png nmr/set01/spectra 'Spectral image' bmse000761 1 stop_ save_ #################### # NMR parameters # #################### ############################## # Assigned chemical shifts # ############################## ################################ # Chemical shift referencing # ################################ save_chem_shift_reference _Chem_shift_reference.Sf_category chem_shift_reference _Chem_shift_reference.Sf_framecode chem_shift_reference _Chem_shift_reference.Entry_ID bmse000761 _Chem_shift_reference.ID 1 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 0.00 internal direct 1.000000000 bmse000761 1 C 13 DSS 'methyl protons' ppm 0.00 internal direct 1.000000000 bmse000761 1 stop_ save_