data_bmse001183 ####################### # Entry information # ####################### save_entry_information _Entry.Sf_category entry_information _Entry.Sf_framecode entry_information _Entry.ID bmse001183 _Entry.Title ; 6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid ; _Entry.Type 'metabolite/natural product' _Entry.Version_type original _Entry.Submission_date 2016-06-24 _Entry.Accession_date 2016-06-24 _Entry.Last_release_date 2016-06-24 _Entry.Original_release_date 2016-06-24 _Entry.Origination author _Entry.NMR_STAR_version 3.1.1.92 _Entry.Original_NMR_STAR_version 3.1.1.92 _Entry.Experimental_method NMR _Entry.Experimental_method_subtype solution _Entry.DOI 10.13018/BMSE001183 loop_ _Entry_author.Ordinal _Entry_author.Given_name _Entry_author.Family_name _Entry_author.First_initial _Entry_author.Middle_initials _Entry_author.Family_title _Entry_author.Entry_ID 1 Maria Nesterova M. . . bmse001183 2 Lawrence Clos L. J. II bmse001183 3 Christopher Stancic C. . . bmse001183 4 Mark Anderson M. E. . bmse001183 5 John Markley J. L. . bmse001183 stop_ loop_ _Entry_src.ID _Entry_src.Project_name _Entry_src.Organization_full_name _Entry_src.Organization_initials _Entry_src.Entry_ID 1 metabolomics 'National Magnetic Resonance Facility at Madison' NMRFAM bmse001183 stop_ loop_ _Data_set.Type _Data_set.Count _Data_set.Entry_ID assigned_chemical_shifts 1 bmse001183 spectral_peak_list 5 bmse001183 stop_ loop_ _Datum.Type _Datum.Count _Datum.Entry_ID '13C chemical shifts' 17 bmse001183 '1H chemical shifts' 20 bmse001183 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 . . 2016-06-24 . original BMRB . bmse001183 2 . . 2017-10-12 2017-10-12 update BMRB 'Remediated Experiment_file loop if present and standardized mol and png file tags.' bmse001183 3 . . 2017-12-19 2017-10-12 update BMRB 'InChI numbering updated according to ALATIS' bmse001183 stop_ save_ ############### # Citations # ############### save_citation_pubchem _Citation.Sf_category citations _Citation.Sf_framecode citation_pubchem _Citation.Entry_ID bmse001183 _Citation.ID 1 _Citation.Class 'reference citation' _Citation.DOI 10.1093/nar/gkl1031 _Citation.PubMed_ID 17170002 _Citation.Title ; Database resources of the National Center for Biotechnology Information ; _Citation.Status published _Citation.Type journal _Citation.Journal_abbrev 'Nucleic Acids Res.' _Citation.Journal_name_full 'Nucleic Acids Research' _Citation.Journal_volume 35 _Citation.Journal_issue 'Database issue' _Citation.Journal_ISSN 0305-1048 _Citation.Page_first D1 _Citation.Page_last D2 _Citation.Year 2007 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 David Wheeler D. L. bmse001183 1 2 Tanya Barrett T. . bmse001183 1 3 Dennis Benson D. A. bmse001183 1 4 Stephen Bryant S. H. bmse001183 1 5 Kathi Canese K. . bmse001183 1 6 Vyacheslav Chetvenin V. . bmse001183 1 7 Deanna Church D. M. bmse001183 1 8 Michael DiCuccio M. . bmse001183 1 9 Ron Edgar R. . bmse001183 1 10 Scott Federhen S. . bmse001183 1 11 Lewis Geer L. Y. bmse001183 1 13 Yuri Kapustin Y. . bmse001183 1 14 Oleg Khovayko O. . bmse001183 1 15 David Landsman D. . bmse001183 1 16 David Lipman D. J. bmse001183 1 17 Thomas Madden T. L. bmse001183 1 18 Donna Maglott D. R. bmse001183 1 19 James Ostell J. . bmse001183 1 20 Vadim Miller V. . bmse001183 1 21 Kim Pruitt K. D. bmse001183 1 22 Gregory Schuler G. D. bmse001183 1 23 Edwin Sequeira E. . bmse001183 1 24 Steven Sherry S. T. bmse001183 1 25 Karl Sirotkin K. . bmse001183 1 26 Alexandre Souvorov A. . bmse001183 1 27 Grigory Starchenko G. . bmse001183 1 28 Roman Tatusov R. L. bmse001183 1 29 Tatiana Tatusova T. A. bmse001183 1 30 Lukas Wagner L. . bmse001183 1 31 Eugene Yaschenko E. . bmse001183 1 stop_ save_ save_citation_nmrbot _Citation.Sf_category citations _Citation.Sf_framecode citation_nmrbot _Citation.Entry_ID bmse001183 _Citation.ID 2 _Citation.Class 'reference citation' _Citation.DOI 10.1007/s11306-012-0490-9 _Citation.PubMed_ID PMC3651530 _Citation.Title ; NMRbot: Python scripts enable high-throughput data collection on current Bruker BioSpin NMR spectrometers ; _Citation.Status published _Citation.Type journal _Citation.Journal_abbrev Metabolomics _Citation.Journal_name_full Metabolomics _Citation.Journal_volume 9 _Citation.Journal_issue 3 _Citation.Journal_ISSN 1573-3882 _Citation.Page_first 558 _Citation.Page_last 563 _Citation.Year 2013 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 Lawrence Clos L. J. II bmse001183 2 2 M Jofre M. F. . bmse001183 2 3 James Ellinger J. J. . bmse001183 2 4 William Westler W. M. . bmse001183 2 5 John Markley J. L. . bmse001183 2 stop_ save_ ############################################# # Molecular system (assembly) description # ############################################# save_assembly_1 _Assembly.Sf_category assembly _Assembly.Sf_framecode assembly_1 _Assembly.Entry_ID bmse001183 _Assembly.ID 1 _Assembly.Name '6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' _Assembly.Number_of_components 1 _Assembly.Paramagnetic no _Assembly.Thiol_state 'not present' 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 '6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' 1 $entity_1 yes native no no bmse001183 1 stop_ loop_ _Atom.Assembly_atom_ID _Atom.Entity_assembly_ID _Atom.Entity_ID _Atom.Comp_index_ID _Atom.Seq_ID _Atom.Comp_ID _Atom.Atom_ID _Atom.Type_symbol _Atom.Entry_ID _Atom.Assembly_ID 1 1 1 1 1 BMET001183 O19 O bmse001183 1 2 1 1 1 1 BMET001183 O20 O bmse001183 1 3 1 1 1 1 BMET001183 O18 O bmse001183 1 4 1 1 1 1 BMET001183 C14 C bmse001183 1 5 1 1 1 1 BMET001183 C16 C bmse001183 1 6 1 1 1 1 BMET001183 C17 C bmse001183 1 7 1 1 1 1 BMET001183 C8 C bmse001183 1 8 1 1 1 1 BMET001183 C7 C bmse001183 1 9 1 1 1 1 BMET001183 C9 C bmse001183 1 10 1 1 1 1 BMET001183 C3 C bmse001183 1 11 1 1 1 1 BMET001183 C13 C bmse001183 1 12 1 1 1 1 BMET001183 C1 C bmse001183 1 13 1 1 1 1 BMET001183 C5 C bmse001183 1 14 1 1 1 1 BMET001183 C11 C bmse001183 1 15 1 1 1 1 BMET001183 C2 C bmse001183 1 16 1 1 1 1 BMET001183 C15 C bmse001183 1 17 1 1 1 1 BMET001183 C10 C bmse001183 1 18 1 1 1 1 BMET001183 C4 C bmse001183 1 19 1 1 1 1 BMET001183 C12 C bmse001183 1 20 1 1 1 1 BMET001183 C6 C bmse001183 1 21 1 1 1 1 BMET001183 H42 H bmse001183 1 22 1 1 1 1 BMET001183 H41 H bmse001183 1 23 1 1 1 1 BMET001183 H40 H bmse001183 1 24 1 1 1 1 BMET001183 H35 H bmse001183 1 25 1 1 1 1 BMET001183 H36 H bmse001183 1 26 1 1 1 1 BMET001183 H33 H bmse001183 1 27 1 1 1 1 BMET001183 H34 H bmse001183 1 28 1 1 1 1 BMET001183 H37 H bmse001183 1 29 1 1 1 1 BMET001183 H38 H bmse001183 1 30 1 1 1 1 BMET001183 H27 H bmse001183 1 31 1 1 1 1 BMET001183 H28 H bmse001183 1 32 1 1 1 1 BMET001183 H21 H bmse001183 1 33 1 1 1 1 BMET001183 H23 H bmse001183 1 34 1 1 1 1 BMET001183 H22 H bmse001183 1 35 1 1 1 1 BMET001183 H30 H bmse001183 1 36 1 1 1 1 BMET001183 H31 H bmse001183 1 37 1 1 1 1 BMET001183 H24 H bmse001183 1 38 1 1 1 1 BMET001183 H26 H bmse001183 1 39 1 1 1 1 BMET001183 H25 H bmse001183 1 40 1 1 1 1 BMET001183 H39 H bmse001183 1 41 1 1 1 1 BMET001183 H29 H bmse001183 1 42 1 1 1 1 BMET001183 H32 H bmse001183 1 stop_ save_ #################################### # Biological polymers and ligands # #################################### save_entity_1 _Entity.Sf_category entity _Entity.Sf_framecode entity_1 _Entity.Entry_ID bmse001183 _Entity.ID 1 _Entity.Name '6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic 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.Nonpolymer_comp_ID BMET001183 _Entity.Paramagnetic no _Entity.Thiol_state 'not present' _Entity.Formula_weight 274.35478 loop_ _Entity_comp_index.ID _Entity_comp_index.Auth_seq_ID _Entity_comp_index.Comp_ID _Entity_comp_index.Comp_label _Entity_comp_index.Entry_ID _Entity_comp_index.Entity_ID 1 1 BMET001183 $chem_comp_1 bmse001183 1 stop_ loop_ _Entity_atom_list.ID _Entity_atom_list.Comp_index_ID _Entity_atom_list.Comp_ID _Entity_atom_list.Atom_ID _Entity_atom_list.Entry_ID _Entity_atom_list.Entity_ID 1 1 BMET001183 O19 bmse001183 1 2 1 BMET001183 O20 bmse001183 1 3 1 BMET001183 O18 bmse001183 1 4 1 BMET001183 C14 bmse001183 1 5 1 BMET001183 C16 bmse001183 1 6 1 BMET001183 C17 bmse001183 1 7 1 BMET001183 C8 bmse001183 1 8 1 BMET001183 C7 bmse001183 1 9 1 BMET001183 C9 bmse001183 1 10 1 BMET001183 C3 bmse001183 1 11 1 BMET001183 C13 bmse001183 1 12 1 BMET001183 C1 bmse001183 1 13 1 BMET001183 C5 bmse001183 1 14 1 BMET001183 C11 bmse001183 1 15 1 BMET001183 C2 bmse001183 1 16 1 BMET001183 C15 bmse001183 1 17 1 BMET001183 C10 bmse001183 1 18 1 BMET001183 C4 bmse001183 1 19 1 BMET001183 C12 bmse001183 1 20 1 BMET001183 C6 bmse001183 1 21 1 BMET001183 H42 bmse001183 1 22 1 BMET001183 H41 bmse001183 1 23 1 BMET001183 H40 bmse001183 1 24 1 BMET001183 H35 bmse001183 1 25 1 BMET001183 H36 bmse001183 1 26 1 BMET001183 H33 bmse001183 1 27 1 BMET001183 H34 bmse001183 1 28 1 BMET001183 H37 bmse001183 1 29 1 BMET001183 H38 bmse001183 1 30 1 BMET001183 H27 bmse001183 1 31 1 BMET001183 H28 bmse001183 1 32 1 BMET001183 H21 bmse001183 1 33 1 BMET001183 H23 bmse001183 1 34 1 BMET001183 H22 bmse001183 1 35 1 BMET001183 H30 bmse001183 1 36 1 BMET001183 H31 bmse001183 1 37 1 BMET001183 H24 bmse001183 1 38 1 BMET001183 H26 bmse001183 1 39 1 BMET001183 H25 bmse001183 1 40 1 BMET001183 H39 bmse001183 1 41 1 BMET001183 H29 bmse001183 1 42 1 BMET001183 H32 bmse001183 1 stop_ save_ #################### # Natural source # #################### 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 bmse001183 _Entity_natural_src_list.ID 1 loop_ _Entity_natural_src.ID _Entity_natural_src.Entity_ID _Entity_natural_src.Entity_label _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.Superkingdom _Entity_natural_src.Genus _Entity_natural_src.Species _Entity_natural_src.Entry_ID _Entity_natural_src.Entity_natural_src_list_ID 1 1 $entity_1 na 'multiple natural sources' yes na na na na na bmse001183 1 stop_ save_ ######################### # Experimental source # ######################### 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 bmse001183 _Entity_experimental_src_list.ID 1 loop_ _Entity_experimental_src.ID _Entity_experimental_src.Entity_ID _Entity_experimental_src.Entity_label _Entity_experimental_src.Production_method _Entity_experimental_src.Entry_ID _Entity_experimental_src.Entity_experimental_src_list_ID 1 1 $entity_1 'chemical synthesis' bmse001183 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 bmse001183 _Chem_comp.ID BMET001183 _Chem_comp.Provenance BMRB _Chem_comp.Name '6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' _Chem_comp.Type non-polymer _Chem_comp.BMRB_code BMET001183 _Chem_comp.Initial_date 2016-06-24 _Chem_comp.Number_atoms_all 42 _Chem_comp.Number_atoms_nh 20 _Chem_comp.InChI_code InChI=1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1 _Chem_comp.Formal_charge 0 _Chem_comp.Paramagnetic no _Chem_comp.Aromatic yes _Chem_comp.Formula C17H22O3 _Chem_comp.Formula_weight 274.35478 _Chem_comp.Formula_mono_iso_wt_nat 274.156894564 _Chem_comp.Formula_mono_iso_wt_13C 291.213926810001 _Chem_comp.Formula_mono_iso_wt_15N 274.156894564 _Chem_comp.Formula_mono_iso_wt_13C_15N 291.213926810001 _Chem_comp.Image_file_name bmse001183.png _Chem_comp.Image_file_format png _Chem_comp.Struct_file_name bmse001183.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 'Podocarpic acid' name bmse001183 BMET001183 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 CC1(C(=O)O)CCCC2(C)c3cc(O)ccc3CCC12 SMILES_CANONICAL RDKit 2016.03.1 bmse001183 BMET001183 CC12CCCC(C1CCC3=C2C=C(C=C3)O)(C)C(=O)O SMILES_CANONICAL PUBCHEM_OPENEYE na bmse001183 BMET001183 C[C@]1(C(=O)O)CCC[C@]2(C)c3cc(O)ccc3CC[C@@H]12 SMILES_ISOMERIC RDKit 2016.03.1 bmse001183 BMET001183 C[C@]12CCC[C@]([C@@H]1CCC3=C2C=C(C=C3)O)(C)C(=O)O SMILES_ISOMERIC PUBCHEM_OPENEYE na bmse001183 BMET001183 ; InChI=1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1 ; INCHI OpenBabel 2.3.2 bmse001183 BMET001183 ; InChI=1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1 ; INCHI PUBCHEM_IUPAC na bmse001183 BMET001183 ; InChI=1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1 ; INCHI RDKit 2016.03.1 bmse001183 BMET001183 OC(=O)C1(C)C2C(C)(CCC1)c1c(ccc(O)c1)CC2 SMILES RDKit 2016.03.1 bmse001183 BMET001183 Oc1ccc2c(c1)[C@@]1(C)CCC[C@]([C@@H]1CC2)(C)C(=O)O SMILES OpenBabel 2.3.2 bmse001183 BMET001183 Oc1ccc2c(c1)[C@@]1(C)CCC[C@]([C@@H]1CC2)(C)C(=O)O SMILES_CANONICAL OpenBabel 2.3.2 bmse001183 BMET001183 VJILEYKNALCDDV-OIISXLGYSA-N INCHI_KEY OpenBabel 2.3.2 bmse001183 BMET001183 VJILEYKNALCDDV-OIISXLGYSA-N INCHI_KEY PUBCHEM_IUPAC na bmse001183 BMET001183 VJILEYKNALCDDV-OIISXLGYSA-N INCHI_KEY RDKit 2016.03.1 bmse001183 BMET001183 InChI=1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1 INCHI ALATIS 1.0 bmse001183 BMET001183 stop_ loop_ _Chem_comp_identifier.Identifier _Chem_comp_identifier.Type _Chem_comp_identifier.Program _Chem_comp_identifier.Program_version _Chem_comp_identifier.Entry_ID _Chem_comp_identifier.Comp_ID '(1S,4aS,10aR)-1,4a-dimethyl-6-oxidanyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' PUBCHEM_IUPAC_SYSTEMATIC_NAME na na bmse001183 BMET001183 '(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' PUBCHEM_IUPAC_CAS_NAME na na bmse001183 BMET001183 '(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' PUBCHEM_IUPAC_NAME na na bmse001183 BMET001183 '(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' PUBCHEM_IUPAC_OPENEYE_NAME na na bmse001183 BMET001183 '(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' PUBCHEM_IUPAC_TRADITIONAL_NAME na na bmse001183 BMET001183 '(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' 'SYSTEMATIC NAME' cactus.nci.nih.gov na bmse001183 BMET001183 '6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' 'SYSTEMATIC NAME' cactus.nci.nih.gov na bmse001183 BMET001183 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.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 O19 O N 0 no 2.3038 -2.4753 1 bmse001183 BMET001183 O20 O N 0 no 3.8137 -3.324 2 bmse001183 BMET001183 O18 O N 0 no 6.4318 3.0119 3 bmse001183 BMET001183 C14 C R 0 no 4.6876 -1.0574 4 bmse001183 BMET001183 C16 C S 0 no 4.6876 -0.0574 5 bmse001183 BMET001183 C17 C S 0 no 3.7937 -1.592 6 bmse001183 BMET001183 C8 C N 0 no 3.7937 0.4773 7 bmse001183 BMET001183 C7 C N 0 no 5.5536 -1.5574 8 bmse001183 BMET001183 C9 C N 0 no 2.8876 -1.0782 9 bmse001183 BMET001183 C3 C N 0 no 2.8876 -0.0365 10 bmse001183 BMET001183 C13 C N 0 yes 5.5536 0.4426 11 bmse001183 BMET001183 C1 C N 0 no 4.6876 0.9426 12 bmse001183 BMET001183 C5 C N 0 no 6.4196 -1.0574 13 bmse001183 BMET001183 C11 C N 0 yes 6.4196 -0.0574 14 bmse001183 BMET001183 C2 C N 0 no 4.3036 -2.4522 15 bmse001183 BMET001183 C15 C N 0 no 3.3037 -2.4638 16 bmse001183 BMET001183 C10 C N 0 yes 5.5376 1.4841 17 bmse001183 BMET001183 C4 C N 0 yes 7.3296 0.4495 18 bmse001183 BMET001183 C12 C N 0 yes 6.4356 2.0119 19 bmse001183 BMET001183 C6 C N 0 yes 7.3377 1.4911 20 bmse001183 BMET001183 H42 H N 0 no 4.6941 -1.9073 21 bmse001183 BMET001183 H41 H N 0 no 4.1982 0.9471 22 bmse001183 BMET001183 H40 H N 0 no 3.4 0.9563 23 bmse001183 BMET001183 H35 H N 0 no 5.1551 -2.0323 24 bmse001183 BMET001183 H36 H N 0 no 5.9521 -2.0323 25 bmse001183 BMET001183 H33 H N 0 no 2.2767 -0.9721 26 bmse001183 BMET001183 H34 H N 0 no 2.6785 -1.6619 27 bmse001183 BMET001183 H37 H N 0 no 2.6785 0.5471 28 bmse001183 BMET001183 H38 H N 0 no 2.2767 -0.1426 29 bmse001183 BMET001183 H27 H N 0 no 5.3076 0.9426 30 bmse001183 BMET001183 H28 H N 0 no 4.6876 1.5626 31 bmse001183 BMET001183 H21 H N 0 no 4.0676 0.9426 32 bmse001183 BMET001183 H23 H N 0 no 6.6317 -1.64 33 bmse001183 BMET001183 H22 H N 0 no 7.0302 -0.9497 34 bmse001183 BMET001183 H30 H N 0 no 3.7703 -2.7684 35 bmse001183 BMET001183 H31 H N 0 no 4.6198 -2.9855 36 bmse001183 BMET001183 H24 H N 0 no 4.837 -2.136 37 bmse001183 BMET001183 H26 H N 0 no 4.9971 1.7879 38 bmse001183 BMET001183 H25 H N 0 no 7.863 0.1333 39 bmse001183 BMET001183 H39 H N 0 no 7.8758 1.799 40 bmse001183 BMET001183 H29 H N 0 no 2.0 -3.0158 41 bmse001183 BMET001183 H32 H N 0 no 6.9675 3.324 42 bmse001183 BMET001183 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 _Chem_comp_bond.Comp_ID 1 ester SING O19 C15 no N 1 bmse001183 BMET001183 2 covalent SING O19 H29 no N 2 bmse001183 BMET001183 3 carbonyl DOUB O20 C15 no N 3 bmse001183 BMET001183 4 covalent SING O18 C12 no N 4 bmse001183 BMET001183 5 covalent SING O18 H32 no N 5 bmse001183 BMET001183 6 covalent SING C14 C16 no N 6 bmse001183 BMET001183 7 covalent SING C14 C17 no N 7 bmse001183 BMET001183 8 covalent SING C14 C7 no N 8 bmse001183 BMET001183 9 covalent SING C14 H42 no N 9 bmse001183 BMET001183 10 covalent SING C16 C8 no N 10 bmse001183 BMET001183 11 covalent SING C16 C13 no N 11 bmse001183 BMET001183 12 covalent SING C16 C1 no N 12 bmse001183 BMET001183 13 covalent SING C17 C9 no N 13 bmse001183 BMET001183 14 covalent SING C17 C2 no N 14 bmse001183 BMET001183 15 covalent SING C17 C15 no N 15 bmse001183 BMET001183 16 covalent SING C8 C3 no N 16 bmse001183 BMET001183 17 covalent SING C8 H41 no N 17 bmse001183 BMET001183 18 covalent SING C8 H40 no N 18 bmse001183 BMET001183 19 covalent SING C7 C5 no N 19 bmse001183 BMET001183 20 covalent SING C7 H35 no N 20 bmse001183 BMET001183 21 covalent SING C7 H36 no N 21 bmse001183 BMET001183 22 covalent SING C9 C3 no N 22 bmse001183 BMET001183 23 covalent SING C9 H33 no N 23 bmse001183 BMET001183 24 covalent SING C9 H34 no N 24 bmse001183 BMET001183 25 covalent SING C3 H37 no N 25 bmse001183 BMET001183 26 covalent SING C3 H38 no N 26 bmse001183 BMET001183 27 covalent AROM C13 C11 yes N 27 bmse001183 BMET001183 28 covalent AROM C13 C10 yes N 28 bmse001183 BMET001183 29 covalent SING C1 H27 no N 29 bmse001183 BMET001183 30 covalent SING C1 H28 no N 30 bmse001183 BMET001183 31 covalent SING C1 H21 no N 31 bmse001183 BMET001183 32 covalent SING C5 C11 no N 32 bmse001183 BMET001183 33 covalent SING C5 H23 no N 33 bmse001183 BMET001183 34 covalent SING C5 H22 no N 34 bmse001183 BMET001183 35 covalent AROM C11 C4 yes N 35 bmse001183 BMET001183 36 covalent SING C2 H30 no N 36 bmse001183 BMET001183 37 covalent SING C2 H31 no N 37 bmse001183 BMET001183 38 covalent SING C2 H24 no N 38 bmse001183 BMET001183 39 covalent AROM C10 C12 yes N 39 bmse001183 BMET001183 40 covalent SING C10 H26 no N 40 bmse001183 BMET001183 41 covalent AROM C4 C6 yes N 41 bmse001183 BMET001183 42 covalent SING C4 H25 no N 42 bmse001183 BMET001183 43 covalent AROM C12 C6 yes N 43 bmse001183 BMET001183 44 covalent SING C6 H39 no N 44 bmse001183 BMET001183 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_ID _Chem_comp_db_link.Comp_ID yes MMCD cq_05847 . bmse001183 BMET001183 yes PubChem 93017 cid bmse001183 BMET001183 stop_ loop_ _Chem_comp_citation.Citation_ID _Chem_comp_citation.Citation_label _Chem_comp_citation.Entry_ID _Chem_comp_citation.Comp_ID 1 $citation_pubchem bmse001183 BMET001183 stop_ save_ ##################################### # Sample contents and methodology # ##################################### ######################## # Sample description # ######################## save_sample_1 _Sample.Sf_category sample _Sample.Sf_framecode sample_1 _Sample.Entry_ID bmse001183 _Sample.ID 1 _Sample.Type solution 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.Vendor _Sample_component.Vendor_product_name _Sample_component.Vendor_product_code _Sample_component.Entry_ID _Sample_component.Sample_ID 1 '6-hydroxy-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid' 'natural abundance' 1 $assembly_1 1 $entity_1 solute 100 mM Sigma-Aldrich 'Podocarpic acid' '119792 Aldrich' bmse001183 1 2 DMSO . . . . . solvent 100.0 % . . . bmse001183 1 3 TMS . . . . . reference 0.05 % . . . bmse001183 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 bmse001183 _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 pressure 1 . atm bmse001183 1 temperature 298 0.1 K bmse001183 1 stop_ save_ ############################ # Computer software used # ############################ save_software_topspin _Software.Sf_category software _Software.Sf_framecode software_topspin _Software.Entry_ID bmse001183 _Software.ID 1 _Software.Name TopSpin _Software.Version 2.1 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/overview.html bmse001183 1 stop_ loop_ _Task.Task _Task.Entry_ID _Task.Software_ID collection bmse001183 1 'data analysis' bmse001183 1 'peak picking' bmse001183 1 processing bmse001183 1 stop_ save_ save_software_nmrbot _Software.Sf_category software _Software.Sf_framecode software_nmrbot _Software.Entry_ID bmse001183 _Software.ID 2 _Software.Name NMRbot _Software.Version 20140226 loop_ _Vendor.Name _Vendor.Electronic_address _Vendor.Entry_ID _Vendor.Software_ID NMRFAM http://www.nmrfam.wisc.edu/software/nmrbot/ bmse001183 2 stop_ loop_ _Task.Task _Task.Entry_ID _Task.Software_ID collection bmse001183 2 stop_ loop_ _Software_citation.Citation_ID _Software_citation.Citation_label _Software_citation.Entry_ID _Software_citation.Software_ID 2 $citation_nmrbot bmse001183 2 stop_ save_ ######################### # Experimental detail # ######################### ################################## # NMR Spectrometer definitions # ################################## save_kerry _NMR_spectrometer.Sf_category NMR_spectrometer _NMR_spectrometer.Sf_framecode kerry _NMR_spectrometer.Entry_ID bmse001183 _NMR_spectrometer.ID 1 _NMR_spectrometer.Details 'equipped with SampleJet automated sample changer' _NMR_spectrometer.Manufacturer Bruker _NMR_spectrometer.Model 'Avance III' _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 bmse001183 _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 $kerry bmse001183 1 2 '2D 1H-1H TOCSY' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 3 '1D 13C' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 4 '1D DEPT90' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 5 '1D DEPT135' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 6 '2D 1H-13C HSQC' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 7 '2D 1H-13C HSQC SW small' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 8 '2D 1H-13C HMBC' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 9 '2D 1H-1H COSY' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 1 10 '2D 1H-13C HSQC-TOCSY-ADIA' yes 1 $sample_1 isotropic 1 $sample_conditions_1 1 $kerry bmse001183 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 1D_1H text/directory nmr/set01 'NMR experiment directory' bmse001183 1 1 1D_1H.xml text/xml nmr/set01/transitions/1D_1H 'TopSpin peak list' bmse001183 1 1 1D_1H_0.png image/png nmr/set01/spectra/1D_1H 'Spectral image' bmse001183 1 2 2D_1H-1H_TOCSY text/directory nmr/set01 'NMR experiment directory' bmse001183 1 2 2D_1H-1H_TOCSY_0.png image/png nmr/set01/spectra/2D_1H-1H_TOCSY 'Spectral image' bmse001183 1 3 1D_13C text/directory nmr/set01 'NMR experiment directory' bmse001183 1 3 1D_13C.xml text/xml nmr/set01/transitions/1D_13C 'TopSpin peak list' bmse001183 1 3 1D_13C_0.png image/png nmr/set01/spectra/1D_13C 'Spectral image' bmse001183 1 4 1D_DEPT90 text/directory nmr/set01 'NMR experiment directory' bmse001183 1 4 1D_DEPT90.xml text/xml nmr/set01/transitions/1D_DEPT90 'TopSpin peak list' bmse001183 1 4 1D_DEPT90_0.png image/png nmr/set01/spectra/1D_DEPT90 'Spectral image' bmse001183 1 5 1D_DEPT135 text/directory nmr/set01 'NMR experiment directory' bmse001183 1 5 1D_DEPT135.xml text/xml nmr/set01/transitions/1D_DEPT135 'TopSpin peak list' bmse001183 1 5 1D_DEPT135_0.png image/png nmr/set01/spectra/1D_DEPT135 'Spectral image' bmse001183 1 6 2D_1H-13C_HSQC text/directory nmr/set01 'NMR experiment directory' bmse001183 1 6 2D_1H-13C_HSQC.xml text/xml nmr/set01/transitions/2D_1H-13C_HSQC 'TopSpin peak list' bmse001183 1 6 2D_1H-13C_HSQC_0.png image/png nmr/set01/spectra/2D_1H-13C_HSQC 'Spectral image' bmse001183 1 7 2D_1H-13C_HSQC_SW_small text/directory nmr/set01 'NMR experiment directory' bmse001183 1 8 2D_1H-13C_HMBC text/directory nmr/set01 'NMR experiment directory' bmse001183 1 8 2D_1H-13C_HMBC_0.png image/png nmr/set01/spectra/2D_1H-13C_HMBC 'Spectral image' bmse001183 1 9 2D_1H-1H_COSY text/directory nmr/set01 'NMR experiment directory' bmse001183 1 9 2D_1H-1H_COSY_0.png image/png nmr/set01/spectra/2D_1H-1H_COSY 'Spectral image' bmse001183 1 10 2D_1H-13C_HSQC-TOCSY-ADIA text/directory nmr/set01 'NMR experiment directory' bmse001183 1 10 2D_1H-13C_HSQC-TOCSY-ADIA_0.png image/png nmr/set01/spectra/2D_1H-13C_HSQC-TOCSY-ADIA 'Spectral image' bmse001183 1 stop_ save_ #################### # NMR parameters # #################### ############################## # Assigned chemical shifts # ############################## ################################ # Chemical shift referencing # ################################ save_chem_shift_ref_set01 _Chem_shift_reference.Sf_category chem_shift_reference _Chem_shift_reference.Sf_framecode chem_shift_ref_set01 _Chem_shift_reference.Entry_ID bmse001183 _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 C 13 TMS 'methyl carbons' ppm 0.0 internal direct 1.0 bmse001183 1 H 1 TMS 'methyl protons' ppm 0.0 internal direct 1.0 bmse001183 1 stop_ save_ ################################### # Assigned chemical shift lists # ################################### ################################################################### # Chemical Shift Ambiguity Index Value Definitions # # # # The values other than 1 are used for those atoms with different # # chemical shifts that cannot be assigned to stereospecific atoms # # or to specific residues or chains. # # # # Index Value Definition # # # # 1 Unique (including isolated methyl protons, # # geminal atoms, and geminal methyl # # groups with identical chemical shifts) # # (e.g. ILE HD11, HD12, HD13 protons) # # 2 Ambiguity of geminal atoms or geminal methyl # # proton groups (e.g. ASP HB2 and HB3 # # protons, LEU CD1 and CD2 carbons, or # # LEU HD11, HD12, HD13 and HD21, HD22, # # HD23 methyl protons) # # 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) # # 6 Intermolecular ambiguities (e.g. ASP 31 CA # # in monomer 1 and ASP 31 CA in monomer 2 # # of an asymmetrical homodimer, duplex # # DNA assignments, or other assignments # # that may apply to atoms in one or more # # molecule in the molecular assembly) # # 9 Ambiguous, specific ambiguity not defined # # # ################################################################### save_chem_shift_set01 _Assigned_chem_shift_list.Sf_category assigned_chemical_shifts _Assigned_chem_shift_list.Sf_framecode chem_shift_set01 _Assigned_chem_shift_list.Entry_ID bmse001183 _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_ref_set01 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 bmse001183 1 2 '2D 1H-1H TOCSY' 1 $sample_1 bmse001183 1 3 '1D 13C' 1 $sample_1 bmse001183 1 4 '1D DEPT90' 1 $sample_1 bmse001183 1 5 '1D DEPT135' 1 $sample_1 bmse001183 1 6 '2D 1H-13C HSQC' 1 $sample_1 bmse001183 1 8 '2D 1H-13C HMBC' 1 $sample_1 bmse001183 1 9 '2D 1H-1H COSY' 1 $sample_1 bmse001183 1 10 '2D 1H-13C HSQC-TOCSY-ADIA' 1 $sample_1 bmse001183 1 stop_ loop_ _Chem_shift_software.Software_ID _Chem_shift_software.Software_label _Chem_shift_software.Entry_ID _Chem_shift_software.Assigned_chem_shift_list_ID 1 $software_topspin bmse001183 1 stop_ loop_ _Atom_chem_shift.ID _Atom_chem_shift.Assembly_atom_ID _Atom_chem_shift.Entity_assembly_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.Ambiguity_code _Atom_chem_shift.Entry_ID _Atom_chem_shift.Assigned_chem_shift_list_ID 1 4 1 1 1 BMET001183 C14 C 13 51.7696 1 bmse001183 1 2 5 1 1 1 BMET001183 C16 C 13 37.9656 1 bmse001183 1 3 6 1 1 1 BMET001183 C17 C 13 42.8981 1 bmse001183 1 4 7 1 1 1 BMET001183 C8 C 13 38.9326 1 bmse001183 1 5 8 1 1 1 BMET001183 C7 C 13 20.851 1 bmse001183 1 6 9 1 1 1 BMET001183 C9 C 13 36.9747 1 bmse001183 1 7 10 1 1 1 BMET001183 C3 C 13 19.6019 1 bmse001183 1 8 11 1 1 1 BMET001183 C13 C 13 148.7337 1 bmse001183 1 9 12 1 1 1 BMET001183 C1 C 13 22.9265 1 bmse001183 1 10 13 1 1 1 BMET001183 C5 C 13 30.5586 1 bmse001183 1 11 14 1 1 1 BMET001183 C11 C 13 124.946 1 bmse001183 1 12 15 1 1 1 BMET001183 C2 C 13 28.2549 1 bmse001183 1 13 16 1 1 1 BMET001183 C15 C 13 178.4842 1 bmse001183 1 14 17 1 1 1 BMET001183 C10 C 13 111.4368 1 bmse001183 1 15 18 1 1 1 BMET001183 C4 C 13 129.424 1 bmse001183 1 16 19 1 1 1 BMET001183 C12 C 13 155.0152 1 bmse001183 1 17 20 1 1 1 BMET001183 C6 C 13 112.8792 1 bmse001183 1 18 21 1 1 1 BMET001183 H42 H 1 1.4405 1 bmse001183 1 19 22 1 1 1 BMET001183 H41 H 1 1.2614 2 bmse001183 1 20 23 1 1 1 BMET001183 H40 H 1 2.1308 2 bmse001183 1 21 24 1 1 1 BMET001183 H35 H 1 1.8507 2 bmse001183 1 22 25 1 1 1 BMET001183 H36 H 1 2.0615 2 bmse001183 1 23 26 1 1 1 BMET001183 H33 H 1 1.0241 2 bmse001183 1 24 27 1 1 1 BMET001183 H34 H 1 2.0882 2 bmse001183 1 25 28 1 1 1 BMET001183 H37 H 1 1.5212 2 bmse001183 1 26 29 1 1 1 BMET001183 H38 H 1 1.9159 2 bmse001183 1 27 30 1 1 1 BMET001183 H27 H 1 1.0307 1 bmse001183 1 28 31 1 1 1 BMET001183 H28 H 1 1.0307 1 bmse001183 1 29 32 1 1 1 BMET001183 H21 H 1 1.0307 1 bmse001183 1 30 33 1 1 1 BMET001183 H23 H 1 2.6056 2 bmse001183 1 31 34 1 1 1 BMET001183 H22 H 1 2.709 2 bmse001183 1 32 35 1 1 1 BMET001183 H30 H 1 1.2032 1 bmse001183 1 33 36 1 1 1 BMET001183 H31 H 1 1.2032 1 bmse001183 1 34 37 1 1 1 BMET001183 H24 H 1 1.2032 1 bmse001183 1 35 38 1 1 1 BMET001183 H26 H 1 6.638 1 bmse001183 1 36 39 1 1 1 BMET001183 H25 H 1 6.7825 1 bmse001183 1 37 40 1 1 1 BMET001183 H39 H 1 6.4793 1 bmse001183 1 stop_ save_ ######################### # Spectral peak lists # ######################### save_spectral_peaks_1D_1H_set01 _Spectral_peak_list.Sf_category spectral_peak_list _Spectral_peak_list.Sf_framecode spectral_peaks_1D_1H_set01 _Spectral_peak_list.Entry_ID bmse001183 _Spectral_peak_list.ID 1 _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.Experiment_ID 1 _Spectral_peak_list.Experiment_name '1D 1H' _Spectral_peak_list.Number_of_spectral_dimensions 1 _Spectral_peak_list.Details 'F1: 1H' loop_ _Spectral_dim.ID _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 H 1 'Full H' 16.03 ppm bmse001183 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_topspin bmse001183 1 stop_ loop_ _Spectral_transition.ID _Spectral_transition.Entry_ID _Spectral_transition.Spectral_peak_list_ID 1 bmse001183 1 2 bmse001183 1 3 bmse001183 1 4 bmse001183 1 5 bmse001183 1 6 bmse001183 1 7 bmse001183 1 8 bmse001183 1 9 bmse001183 1 10 bmse001183 1 11 bmse001183 1 12 bmse001183 1 13 bmse001183 1 14 bmse001183 1 15 bmse001183 1 16 bmse001183 1 17 bmse001183 1 18 bmse001183 1 19 bmse001183 1 20 bmse001183 1 21 bmse001183 1 22 bmse001183 1 23 bmse001183 1 24 bmse001183 1 25 bmse001183 1 26 bmse001183 1 27 bmse001183 1 28 bmse001183 1 29 bmse001183 1 30 bmse001183 1 31 bmse001183 1 32 bmse001183 1 33 bmse001183 1 34 bmse001183 1 35 bmse001183 1 36 bmse001183 1 37 bmse001183 1 38 bmse001183 1 39 bmse001183 1 40 bmse001183 1 41 bmse001183 1 42 bmse001183 1 43 bmse001183 1 44 bmse001183 1 45 bmse001183 1 46 bmse001183 1 47 bmse001183 1 48 bmse001183 1 49 bmse001183 1 50 bmse001183 1 51 bmse001183 1 52 bmse001183 1 53 bmse001183 1 54 bmse001183 1 55 bmse001183 1 56 bmse001183 1 57 bmse001183 1 58 bmse001183 1 59 bmse001183 1 60 bmse001183 1 61 bmse001183 1 62 bmse001183 1 63 bmse001183 1 64 bmse001183 1 65 bmse001183 1 66 bmse001183 1 67 bmse001183 1 stop_ loop_ _Spectral_transition_general_char.Spectral_transition_ID _Spectral_transition_general_char.Intensity_val _Spectral_transition_general_char.Measurement_method _Spectral_transition_general_char.Entry_ID _Spectral_transition_general_char.Spectral_peak_list_ID 1 0.53 'relative height' bmse001183 1 2 0.69 'relative height' bmse001183 1 3 2.49 'relative height' bmse001183 1 4 2.75 'relative height' bmse001183 1 5 3.08 'relative height' bmse001183 1 6 3.21 'relative height' bmse001183 1 7 2.00 'relative height' bmse001183 1 8 1.84 'relative height' bmse001183 1 9 1.83 'relative height' bmse001183 1 10 1.71 'relative height' bmse001183 1 11 0.54 'relative height' bmse001183 1 12 0.52 'relative height' bmse001183 1 13 0.56 'relative height' bmse001183 1 14 0.93 'relative height' bmse001183 1 15 0.93 'relative height' bmse001183 1 16 0.47 'relative height' bmse001183 1 17 0.58 'relative height' bmse001183 1 18 0.58 'relative height' bmse001183 1 19 0.66 'relative height' bmse001183 1 20 0.37 'relative height' bmse001183 1 21 0.32 'relative height' bmse001183 1 22 0.51 'relative height' bmse001183 1 23 0.68 'relative height' bmse001183 1 24 0.47 'relative height' bmse001183 1 25 0.83 'relative height' bmse001183 1 26 1.23 'relative height' bmse001183 1 27 1.26 'relative height' bmse001183 1 28 1.10 'relative height' bmse001183 1 29 0.62 'relative height' bmse001183 1 30 0.78 'relative height' bmse001183 1 31 0.67 'relative height' bmse001183 1 32 0.20 'relative height' bmse001183 1 33 0.40 'relative height' bmse001183 1 34 0.63 'relative height' bmse001183 1 35 0.38 'relative height' bmse001183 1 36 0.48 'relative height' bmse001183 1 37 0.74 'relative height' bmse001183 1 38 0.62 'relative height' bmse001183 1 39 0.40 'relative height' bmse001183 1 40 0.77 'relative height' bmse001183 1 41 0.68 'relative height' bmse001183 1 42 0.65 'relative height' bmse001183 1 43 0.61 'relative height' bmse001183 1 44 0.28 'relative height' bmse001183 1 45 0.22 'relative height' bmse001183 1 46 0.73 'relative height' bmse001183 1 47 0.57 'relative height' bmse001183 1 48 0.37 'relative height' bmse001183 1 49 0.63 'relative height' bmse001183 1 50 1.53 'relative height' bmse001183 1 51 1.41 'relative height' bmse001183 1 52 0.08 'relative height' bmse001183 1 53 0.44 'relative height' bmse001183 1 54 0.48 'relative height' bmse001183 1 55 0.84 'relative height' bmse001183 1 56 0.79 'relative height' bmse001183 1 57 0.47 'relative height' bmse001183 1 58 0.41 'relative height' bmse001183 1 59 14.39 'relative height' bmse001183 1 60 0.09 'relative height' bmse001183 1 61 0.11 'relative height' bmse001183 1 62 0.50 'relative height' bmse001183 1 63 0.65 'relative height' bmse001183 1 64 15.00 'relative height' bmse001183 1 65 1.23 'relative height' bmse001183 1 66 0.54 'relative height' bmse001183 1 67 0.42 'relative height' bmse001183 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 12.0988 bmse001183 1 2 1 8.9560 bmse001183 1 3 1 6.7915 bmse001183 1 4 1 6.7749 bmse001183 1 5 1 6.6381 bmse001183 1 6 1 6.6332 bmse001183 1 7 1 6.4914 bmse001183 1 8 1 6.4865 bmse001183 1 9 1 6.4750 bmse001183 1 10 1 6.4701 bmse001183 1 11 1 3.3766 bmse001183 1 12 1 2.7368 bmse001183 1 13 1 2.7285 bmse001183 1 14 1 2.7054 bmse001183 1 15 1 2.6957 bmse001183 1 16 1 2.6357 bmse001183 1 17 1 2.6238 bmse001183 1 18 1 2.6102 bmse001183 1 19 1 2.5982 bmse001183 1 20 1 2.5777 bmse001183 1 21 1 2.5658 bmse001183 1 22 1 2.5106 bmse001183 1 23 1 2.5071 bmse001183 1 24 1 2.5035 bmse001183 1 25 1 2.1426 bmse001183 1 26 1 2.1159 bmse001183 1 27 1 2.1092 bmse001183 1 28 1 2.0804 bmse001183 1 29 1 2.0634 bmse001183 1 30 1 2.0477 bmse001183 1 31 1 2.0363 bmse001183 1 32 1 1.9567 bmse001183 1 33 1 1.9360 bmse001183 1 34 1 1.9292 bmse001183 1 35 1 1.9222 bmse001183 1 36 1 1.9086 bmse001183 1 37 1 1.9015 bmse001183 1 38 1 1.8953 bmse001183 1 39 1 1.8845 bmse001183 1 40 1 1.8699 bmse001183 1 41 1 1.8594 bmse001183 1 42 1 1.8436 bmse001183 1 43 1 1.8333 bmse001183 1 44 1 1.8181 bmse001183 1 45 1 1.8072 bmse001183 1 46 1 1.5347 bmse001183 1 47 1 1.5286 bmse001183 1 48 1 1.5208 bmse001183 1 49 1 1.5070 bmse001183 1 50 1 1.4507 bmse001183 1 51 1 1.4285 bmse001183 1 52 1 1.3281 bmse001183 1 53 1 1.2909 bmse001183 1 54 1 1.2833 bmse001183 1 55 1 1.2644 bmse001183 1 56 1 1.2567 bmse001183 1 57 1 1.2379 bmse001183 1 58 1 1.2303 bmse001183 1 59 1 1.2022 bmse001183 1 60 1 1.1542 bmse001183 1 61 1 1.0726 bmse001183 1 62 1 1.0548 bmse001183 1 63 1 1.0466 bmse001183 1 64 1 1.0301 bmse001183 1 65 1 1.0204 bmse001183 1 66 1 1.0015 bmse001183 1 67 1 0.9935 bmse001183 1 stop_ save_ save_spectral_peaks_1D_13C_set01 _Spectral_peak_list.Sf_category spectral_peak_list _Spectral_peak_list.Sf_framecode spectral_peaks_1D_13C_set01 _Spectral_peak_list.Entry_ID bmse001183 _Spectral_peak_list.ID 3 _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.Experiment_ID 3 _Spectral_peak_list.Experiment_name '1D 13C' _Spectral_peak_list.Number_of_spectral_dimensions 1 _Spectral_peak_list.Details 'F1: 13C' loop_ _Spectral_dim.ID _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 C 13 'Full C' 248.61 ppm bmse001183 3 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_topspin bmse001183 3 stop_ loop_ _Spectral_transition.ID _Spectral_transition.Entry_ID _Spectral_transition.Spectral_peak_list_ID 1 bmse001183 3 2 bmse001183 3 3 bmse001183 3 4 bmse001183 3 5 bmse001183 3 6 bmse001183 3 7 bmse001183 3 8 bmse001183 3 9 bmse001183 3 10 bmse001183 3 11 bmse001183 3 12 bmse001183 3 13 bmse001183 3 14 bmse001183 3 15 bmse001183 3 16 bmse001183 3 17 bmse001183 3 stop_ loop_ _Spectral_transition_general_char.Spectral_transition_ID _Spectral_transition_general_char.Intensity_val _Spectral_transition_general_char.Measurement_method _Spectral_transition_general_char.Entry_ID _Spectral_transition_general_char.Spectral_peak_list_ID 1 1.53 'relative height' bmse001183 3 2 1.61 'relative height' bmse001183 3 3 1.05 'relative height' bmse001183 3 4 1.30 'relative height' bmse001183 3 5 1.16 'relative height' bmse001183 3 6 1.11 'relative height' bmse001183 3 7 1.37 'relative height' bmse001183 3 8 1.55 'relative height' bmse001183 3 9 2.74 'relative height' bmse001183 3 10 1.12 'relative height' bmse001183 3 11 2.71 'relative height' bmse001183 3 12 0.97 'relative height' bmse001183 3 13 1.17 'relative height' bmse001183 3 14 1.78 'relative height' bmse001183 3 15 2.45 'relative height' bmse001183 3 16 1.07 'relative height' bmse001183 3 17 1.10 'relative height' bmse001183 3 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 1 178.4842 bmse001183 3 2 1 155.0152 bmse001183 3 3 1 148.7337 bmse001183 3 4 1 129.4240 bmse001183 3 5 1 124.9460 bmse001183 3 6 1 112.8792 bmse001183 3 7 1 111.4368 bmse001183 3 8 1 51.7696 bmse001183 3 9 1 42.8981 bmse001183 3 10 1 38.9326 bmse001183 3 11 1 37.9656 bmse001183 3 12 1 36.9747 bmse001183 3 13 1 30.5586 bmse001183 3 14 1 28.2549 bmse001183 3 15 1 22.9265 bmse001183 3 16 1 20.8510 bmse001183 3 17 1 19.6019 bmse001183 3 stop_ loop_ _Assigned_spectral_transition.Spectral_transition_ID _Assigned_spectral_transition.Spectral_dim_ID _Assigned_spectral_transition.Assembly_atom_ID _Assigned_spectral_transition.Val _Assigned_spectral_transition.Assigned_chem_shift_list_ID _Assigned_spectral_transition.Atom_chem_shift_ID _Assigned_spectral_transition.Entity_assembly_ID _Assigned_spectral_transition.Entity_ID _Assigned_spectral_transition.Comp_index_ID _Assigned_spectral_transition.Comp_ID _Assigned_spectral_transition.Atom_ID _Assigned_spectral_transition.Entry_ID _Assigned_spectral_transition.Spectral_peak_list_ID 1 1 16 178.4842 1 13 1 1 1 BMET001183 C15 bmse001183 3 10 1 7 38.9326 1 4 1 1 1 BMET001183 C8 bmse001183 3 11 1 5 37.9656 1 2 1 1 1 BMET001183 C16 bmse001183 3 12 1 9 36.9747 1 6 1 1 1 BMET001183 C9 bmse001183 3 13 1 13 30.5586 1 10 1 1 1 BMET001183 C5 bmse001183 3 14 1 15 28.2549 1 12 1 1 1 BMET001183 C2 bmse001183 3 15 1 12 22.9265 1 9 1 1 1 BMET001183 C1 bmse001183 3 16 1 8 20.8510 1 5 1 1 1 BMET001183 C7 bmse001183 3 17 1 10 19.6019 1 7 1 1 1 BMET001183 C3 bmse001183 3 2 1 19 155.0152 1 16 1 1 1 BMET001183 C12 bmse001183 3 3 1 11 148.7337 1 8 1 1 1 BMET001183 C13 bmse001183 3 4 1 18 129.4240 1 15 1 1 1 BMET001183 C4 bmse001183 3 5 1 14 124.9460 1 11 1 1 1 BMET001183 C11 bmse001183 3 6 1 20 112.8792 1 17 1 1 1 BMET001183 C6 bmse001183 3 7 1 17 111.4368 1 14 1 1 1 BMET001183 C10 bmse001183 3 8 1 4 51.7696 1 1 1 1 1 BMET001183 C14 bmse001183 3 9 1 6 42.8981 1 3 1 1 1 BMET001183 C17 bmse001183 3 stop_ save_ save_spectral_peaks_1D_DEPT90_set01 _Spectral_peak_list.Sf_category spectral_peak_list _Spectral_peak_list.Sf_framecode spectral_peaks_1D_DEPT90_set01 _Spectral_peak_list.Entry_ID bmse001183 _Spectral_peak_list.ID 4 _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.Experiment_ID 4 _Spectral_peak_list.Experiment_name '1D DEPT90' _Spectral_peak_list.Number_of_spectral_dimensions 1 _Spectral_peak_list.Details 'F1: 13C' loop_ _Spectral_dim.ID _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 C 13 'Full C' 236.77 ppm bmse001183 4 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_topspin bmse001183 4 stop_ loop_ _Spectral_transition.ID _Spectral_transition.Entry_ID _Spectral_transition.Spectral_peak_list_ID 1 bmse001183 4 2 bmse001183 4 3 bmse001183 4 4 bmse001183 4 stop_ loop_ _Spectral_transition_general_char.Spectral_transition_ID _Spectral_transition_general_char.Intensity_val _Spectral_transition_general_char.Measurement_method _Spectral_transition_general_char.Entry_ID _Spectral_transition_general_char.Spectral_peak_list_ID 1 14.07 'relative height' bmse001183 4 2 12.35 'relative height' bmse001183 4 3 12.61 'relative height' bmse001183 4 4 15.00 'relative height' bmse001183 4 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 1 129.4107 bmse001183 4 2 1 112.8630 bmse001183 4 3 1 111.4196 bmse001183 4 4 1 51.7552 bmse001183 4 stop_ save_ save_spectral_peaks_1D_DEPT135_set01 _Spectral_peak_list.Sf_category spectral_peak_list _Spectral_peak_list.Sf_framecode spectral_peaks_1D_DEPT135_set01 _Spectral_peak_list.Entry_ID bmse001183 _Spectral_peak_list.ID 5 _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.Experiment_ID 5 _Spectral_peak_list.Experiment_name '1D DEPT135' _Spectral_peak_list.Number_of_spectral_dimensions 1 _Spectral_peak_list.Details 'F1: 13C' loop_ _Spectral_dim.ID _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 C 13 'Full C' 236.77 ppm bmse001183 5 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_topspin bmse001183 5 stop_ loop_ _Spectral_transition.ID _Spectral_transition.Entry_ID _Spectral_transition.Spectral_peak_list_ID 1 bmse001183 5 2 bmse001183 5 3 bmse001183 5 4 bmse001183 5 5 bmse001183 5 6 bmse001183 5 7 bmse001183 5 8 bmse001183 5 9 bmse001183 5 10 bmse001183 5 11 bmse001183 5 stop_ loop_ _Spectral_transition_general_char.Spectral_transition_ID _Spectral_transition_general_char.Intensity_val _Spectral_transition_general_char.Measurement_method _Spectral_transition_general_char.Entry_ID _Spectral_transition_general_char.Spectral_peak_list_ID 1 8.60 'relative height' bmse001183 5 2 7.66 'relative height' bmse001183 5 3 7.81 'relative height' bmse001183 5 4 9.06 'relative height' bmse001183 5 5 -6.77 'relative height' bmse001183 5 6 -6.77 'relative height' bmse001183 5 7 -7.72 'relative height' bmse001183 5 8 15.00 'relative height' bmse001183 5 9 13.89 'relative height' bmse001183 5 10 -7.08 'relative height' bmse001183 5 11 -7.15 'relative height' bmse001183 5 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 1 129.4262 bmse001183 5 2 1 112.8785 bmse001183 5 3 1 111.4351 bmse001183 5 4 1 51.7707 bmse001183 5 5 1 38.9319 bmse001183 5 6 1 36.9741 bmse001183 5 7 1 30.5573 bmse001183 5 8 1 28.2557 bmse001183 5 9 1 22.9243 bmse001183 5 10 1 20.8504 bmse001183 5 11 1 19.5999 bmse001183 5 stop_ save_ save_spectral_peaks_2D_1H_13C_HSQC_set01 _Spectral_peak_list.Sf_category spectral_peak_list _Spectral_peak_list.Sf_framecode spectral_peaks_2D_1H_13C_HSQC_set01 _Spectral_peak_list.Entry_ID bmse001183 _Spectral_peak_list.ID 6 _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.Experiment_ID 6 _Spectral_peak_list.Experiment_name '2D 1H-13C HSQC' _Spectral_peak_list.Number_of_spectral_dimensions 2 _Spectral_peak_list.Details 'F1: 13C, F2: 1H' loop_ _Spectral_dim.ID _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 C 13 'Full C' 165.64 ppm bmse001183 6 2 H 1 'Full H' 12.99 ppm bmse001183 6 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_topspin bmse001183 6 stop_ loop_ _Spectral_transition.ID _Spectral_transition.Entry_ID _Spectral_transition.Spectral_peak_list_ID 1 bmse001183 6 2 bmse001183 6 3 bmse001183 6 4 bmse001183 6 5 bmse001183 6 6 bmse001183 6 7 bmse001183 6 8 bmse001183 6 9 bmse001183 6 10 bmse001183 6 11 bmse001183 6 12 bmse001183 6 13 bmse001183 6 14 bmse001183 6 15 bmse001183 6 16 bmse001183 6 stop_ loop_ _Spectral_transition_general_char.Spectral_transition_ID _Spectral_transition_general_char.Intensity_val _Spectral_transition_general_char.Measurement_method _Spectral_transition_general_char.Entry_ID _Spectral_transition_general_char.Spectral_peak_list_ID 1 192079.60 'absolute height' bmse001183 6 2 199216.34 'absolute height' bmse001183 6 3 163054.09 'absolute height' bmse001183 6 4 143327.27 'absolute height' bmse001183 6 5 73324.02 'absolute height' bmse001183 6 6 66653.29 'absolute height' bmse001183 6 7 89038.58 'absolute height' bmse001183 6 8 87884.05 'absolute height' bmse001183 6 9 74783.43 'absolute height' bmse001183 6 10 93361.90 'absolute height' bmse001183 6 11 471877.48 'absolute height' bmse001183 6 12 344931.87 'absolute height' bmse001183 6 13 92141.19 'absolute height' bmse001183 6 14 63143.60 'absolute height' bmse001183 6 15 48602.20 'absolute height' bmse001183 6 16 78497.44 'absolute height' bmse001183 6 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 1 129.5310 bmse001183 6 1 2 6.7825 bmse001183 6 2 1 112.8684 bmse001183 6 2 2 6.4793 bmse001183 6 3 1 111.5186 bmse001183 6 3 2 6.6380 bmse001183 6 4 1 51.7487 bmse001183 6 4 2 1.4405 bmse001183 6 5 1 38.8972 bmse001183 6 5 2 1.2614 bmse001183 6 6 1 36.9259 bmse001183 6 6 2 1.0241 bmse001183 6 7 1 38.8796 bmse001183 6 7 2 2.1308 bmse001183 6 8 1 36.9259 bmse001183 6 8 2 2.0882 bmse001183 6 9 1 30.6367 bmse001183 6 9 2 2.6056 bmse001183 6 10 1 30.6367 bmse001183 6 10 2 2.7090 bmse001183 6 11 1 28.2547 bmse001183 6 11 2 1.2032 bmse001183 6 12 1 22.9159 bmse001183 6 12 2 1.0307 bmse001183 6 13 1 20.9446 bmse001183 6 13 2 2.0615 bmse001183 6 14 1 20.9036 bmse001183 6 14 2 1.8507 bmse001183 6 15 1 19.5483 bmse001183 6 15 2 1.9159 bmse001183 6 16 1 19.5073 bmse001183 6 16 2 1.5212 bmse001183 6 stop_ save_