data_bmst000242 ####################### # Entry information # ####################### save_entry_information _Entry.Sf_category entry_information _Entry.Sf_framecode entry_information _Entry.ID bmst000242 _Entry.Title Thiamin _Entry.Version_type update _Entry.Submission_date 2006-04-13 _Entry.Accession_date 2006-04-13 _Entry.Last_release_date 2011-09-14 _Entry.Original_release_date 2006-04-13 _Entry.Origination author _Entry.NMR_STAR_version 3.1.1.7 _Entry.Original_NMR_STAR_version 'NMR STAR v3.1' _Entry.Experimental_method NMR _Entry.Experimental_method_subtype theoretical _Entry.Details ? _Entry.BMRB_internal_directory_name Thiamin 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 William Westler M. ? bmst000242 2 John Markley L. ? bmst000242 stop_ loop_ _Entry_src.ID _Entry_src.Project_name _Entry_src.Organization_full_name _Entry_src.Organization_initials _Entry_src.Entry_ID 1 metabolics 'Madison Metabolomics Consortium' MMC bmst000242 stop_ loop_ _Data_set.Type _Data_set.Count _Data_set.Entry_ID other_data_list 1 bmst000242 stop_ loop_ _Datum.Type _Datum.Count _Datum.Entry_ID 'theoretical chemical shifts' 1 bmst000242 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 . . 2006-04-13 2006-04-13 original BMRB 'Original theoretical calculations from NMRFAM' bmst000242 2 . . 2008-11-18 2008-11-18 update BMRB 'updated the file to match latest NMR STAR dictionary' bmst000242 3 . . 2008-11-25 2008-11-25 update BMRB 'fixed enumerations: N should be no' bmst000242 4 . . 2010-09-16 2010-09-16 update BMRB 'Removed Shielding_tensor_list_ID and Shielding_tensor_list_label from theoretical_chem_shifts' bmst000242 5 . . 2011-09-14 2011-09-14 update BMRB 'Partially brought up to date with latest Dictionary' bmst000242 6 . . 2017-10-12 2017-10-12 update BMRB 'Remediated Experiment_file loop if present and standardized mol and png file tags.' bmst000242 stop_ loop_ _Auxiliary_files.ID _Auxiliary_files.URI _Auxiliary_files.DOI _Auxiliary_files.Path _Auxiliary_files.Format _Auxiliary_files.Details _Auxiliary_files.Entry_ID 1 . . Thiamin_3668_opt.pdb x-chemical/x-pdb 'Name of the file containing the atomic coordinates' bmst000242 2 . . Thiamin_3668.g03.shifts text/plain 'Name of the file containing theoretical chemical shift data' bmst000242 stop_ save_ ############### # Citations # ############### save_citations _Citation.Sf_category citations _Citation.Sf_framecode citations _Citation.Entry_ID bmst000242 _Citation.ID 1 _Citation.Class 'reference citation' _Citation.PubMed_ID 18940862 _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 _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 D. Wheeler D. L. ? bmst000242 1 2 T. Barrett T. ? ? bmst000242 1 3 D. Benson D. A. ? bmst000242 1 4 S. Bryant S. H. ? bmst000242 1 5 K. Canese K. ? ? bmst000242 1 6 V. Chetvenin V. ? ? bmst000242 1 7 D. Church D. M. ? bmst000242 1 8 M. DiCuccio M. ? ? bmst000242 1 9 R. Edgar R. ? ? bmst000242 1 10 S. Federhen S. ? ? bmst000242 1 11 L. Geer L. Y. ? bmst000242 1 12 W. Helmberg W. ? ? bmst000242 1 13 Y. Kapustin Y. ? ? bmst000242 1 14 D. Kenton D. L. ? bmst000242 1 15 O. Khovayko O. ? ? bmst000242 1 16 D. Lipman D. J. ? bmst000242 1 17 T. Madden T. L. ? bmst000242 1 18 D. Maglott D. R. ? bmst000242 1 19 J. Ostell J. ? ? bmst000242 1 20 K. Pruitt K. D. ? bmst000242 1 21 G. Schuler G. D. ? bmst000242 1 22 L. Schriml L. M. ? bmst000242 1 23 E. Sequeira E. ? ? bmst000242 1 24 S. Sherry S. T. ? bmst000242 1 25 K. Sirotkin K. ? ? bmst000242 1 26 A. Souvorov A. ? ? bmst000242 1 27 G. Starchenko G. ? ? bmst000242 1 28 T. Suzek T. O. ? bmst000242 1 29 R. Tatusov R. ? ? bmst000242 1 30 T. Tatusova T. A. ? bmst000242 1 31 L. Bagner L. ? ? bmst000242 1 32 E. Yaschenko E. ? ? bmst000242 1 stop_ save_ ############################################# # Molecular system (assembly) description # ############################################# save_assembly _Assembly.Sf_category assembly _Assembly.Sf_framecode assembly _Assembly.Entry_ID bmst000242 _Assembly.ID 1 _Assembly.Name ASSEMBLY_NAME _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 ENT_NAME 1 $Thiamin yes native no no ? ? ? bmst000242 1 stop_ save_ #################################### # Biological polymers and ligands # #################################### save_Thiamin _Entity.Sf_category entity _Entity.Sf_framecode Thiamin _Entity.Entry_ID bmst000242 _Entity.ID 1 _Entity.BMRB_code ? _Entity.Name Thiamin _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 bmst000242 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 bmst000242 _Chem_comp.ID 1 _Chem_comp.Provenance PubChem _Chem_comp.Name Thiamin _Chem_comp.Type non-polymer _Chem_comp.BMRB_code ? _Chem_comp.PDB_code ? _Chem_comp.InChI_code ; InChI=1/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1/f/h13H2 ; _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 'C12 H17 N4 O S +' _Chem_comp.Formula_weight 265.3540314201 _Chem_comp.Formula_mono_iso_wt_nat 265.111758299 _Chem_comp.Formula_mono_iso_wt_13C 277.152016352 _Chem_comp.Formula_mono_iso_wt_15N 269.099897871 _Chem_comp.Formula_mono_iso_wt_13C_15N 277.152016352 _Chem_comp.Image_file_name bmst000242.png _Chem_comp.Image_file_format png _Chem_comp.Topo_file_name ? _Chem_comp.Topo_file_format ? _Chem_comp.Struct_file_name bmst000242.mol _Chem_comp.Struct_file_format mol _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 Aneurin synonym bmst000242 1 'Vitamin B1' synonym bmst000242 1 'Antiberiberi factor' synonym bmst000242 1 Thiamine synonym bmst000242 1 Thiamin synonym bmst000242 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 ; 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1-thia-3-azoniacyclopenta-2,4-dien-5-yl]ethanol ; IUPAC bmst000242 1 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl]ethanol IUPAC_TRADITIONAL bmst000242 1 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl]ethanol IUPAC_OPENEYE bmst000242 1 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl]ethanol IUPAC_CAS bmst000242 1 ; 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1-thia-3-azoniacyclopenta-2,4-dien-5-yl]ethanol ; IUPAC_SYSTEMATIC bmst000242 1 stop_ loop_ _Chem_comp_SMILES.Type _Chem_comp_SMILES.String _Chem_comp_SMILES.Entry_ID _Chem_comp_SMILES.Comp_ID Canonical CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO bmst000242 1 stop_ loop_ _Chem_comp_atom.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.PDBX_ordinal _Chem_comp_atom.Entry_ID _Chem_comp_atom.Comp_ID S1 S ? ? ? ? 2.3090 1.0304 -1.109 -2.732 1.588 1 bmst000242 1 O2 O ? ? ? ? 4.0779 3.5620 3.035 -4.399 -0.112 2 bmst000242 1 N3 N ? ? ? ? 2.8090 -3.5084 0.412 3.654 0.657 3 bmst000242 1 N4 N ? ? ? ? 2.8090 -0.5084 -0.850 -0.236 1.336 4 bmst000242 1 N5 N ? ? ? ? 4.5411 -3.5084 0.031 3.369 -1.599 5 bmst000242 1 N6 N ? ? ? ? 5.4071 -2.0084 -1.360 1.647 -2.488 6 bmst000242 1 C7 C ? ? ? ? 3.4901 2.7530 1.886 -3.587 -0.205 7 bmst000242 1 C8 C ? ? ? ? 3.8968 1.8394 1.673 -3.018 1.210 8 bmst000242 1 C9 C ? ? ? ? 2.8090 -1.5084 -1.213 1.216 1.263 9 bmst000242 1 C10 C ? ? ? ? 6.2731 -3.5084 -0.259 3.194 -4.006 10 bmst000242 1 C11 C ? ? ? ? 4.5691 -0.2296 1.611 0.189 0.940 11 bmst000242 1 C12 C ? ? ? ? 5.4071 -3.0084 -0.535 2.709 -2.613 12 bmst000242 1 C13 C ? ? ? ? 3.6750 -3.0084 -0.209 2.946 -0.349 13 bmst000242 1 C14 C ? ? ? ? 3.3090 1.0304 0.496 -2.094 1.316 14 bmst000242 1 C15 C ? ? ? ? 3.6180 0.0794 0.455 -0.728 1.197 15 bmst000242 1 C16 C ? ? ? ? 3.6750 -2.0084 -1.000 1.798 -0.109 16 bmst000242 1 C17 C ? ? ? ? 2.0000 0.0794 -1.768 -1.174 1.545 17 bmst000242 1 C18 C ? ? ? ? 4.5411 -1.5084 -1.568 1.219 -1.247 18 bmst000242 1 H19 H ? ? ? ? 3.8257 4.1284 3.215 -4.794 -0.979 19 bmst000242 1 H20 H ? ? ? ? 2.8090 -4.1284 0.870 4.493 0.317 20 bmst000242 1 H21 H ? ? ? ? 2.2721 -3.1984 -0.089 3.801 1.523 21 bmst000242 1 H22 H ? ? ? ? 3.0594 3.1990 0.995 -4.159 -0.513 22 bmst000242 1 H23 H ? ? ? ? 2.9761 2.4063 2.014 -2.760 -0.922 23 bmst000242 1 H24 H ? ? ? ? 4.3275 1.3935 1.566 -3.857 1.905 24 bmst000242 1 H25 H ? ? ? ? 4.4108 2.1861 2.584 -2.486 1.506 25 bmst000242 1 H26 H ? ? ? ? 2.1984 -1.4007 -2.255 1.272 1.593 26 bmst000242 1 H27 H ? ? ? ? 2.5970 -2.0910 -0.605 1.719 2.018 27 bmst000242 1 H28 H ? ? ? ? 5.9631 -4.0453 0.029 2.357 -4.649 28 bmst000242 1 H29 H ? ? ? ? 6.8101 -3.8184 -1.172 3.624 -4.435 29 bmst000242 1 H30 H ? ? ? ? 6.5831 -2.9715 0.525 3.953 -4.002 30 bmst000242 1 H31 H ? ? ? ? 5.1587 -0.4212 1.646 0.495 -0.111 31 bmst000242 1 H32 H ? ? ? ? 4.7607 0.3600 1.563 1.100 1.544 32 bmst000242 1 H33 H ? ? ? ? 4.3775 -0.8193 2.547 -0.321 1.174 33 bmst000242 1 H34 H ? ? ? ? 1.4103 -0.1122 -2.817 -0.949 1.680 34 bmst000242 1 H35 H ? ? ? ? 4.5411 -0.8884 -2.218 0.348 -1.150 35 bmst000242 1 stop_ loop_ _Atom_nomenclature.Atom_ID _Atom_nomenclature.Atom_name _Atom_nomenclature.Naming_system _Atom_nomenclature.Entry_ID _Atom_nomenclature.Comp_ID S1 S1 ? bmst000242 1 O2 O2 ? bmst000242 1 N3 N3 ? bmst000242 1 N4 N4 ? bmst000242 1 N5 N5 ? bmst000242 1 N6 N6 ? bmst000242 1 C7 C7 ? bmst000242 1 C8 C8 ? bmst000242 1 C9 C9 ? bmst000242 1 C10 C10 ? bmst000242 1 C11 C11 ? bmst000242 1 C12 C12 ? bmst000242 1 C13 C13 ? bmst000242 1 C14 C14 ? bmst000242 1 C15 C15 ? bmst000242 1 C16 C16 ? bmst000242 1 C17 C17 ? bmst000242 1 C18 C18 ? bmst000242 1 H19 H19 ? bmst000242 1 H20 H20 ? bmst000242 1 H21 H21 ? bmst000242 1 H22 H22 ? bmst000242 1 H23 H23 ? bmst000242 1 H24 H24 ? bmst000242 1 H25 H25 ? bmst000242 1 H26 H26 ? bmst000242 1 H27 H27 ? bmst000242 1 H28 H28 ? bmst000242 1 H29 H29 ? bmst000242 1 H30 H30 ? bmst000242 1 H31 H31 ? bmst000242 1 H32 H32 ? bmst000242 1 H33 H33 ? bmst000242 1 H34 H34 ? bmst000242 1 H35 H35 ? bmst000242 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 S1 C14 ? bmst000242 1 2 covalent SING S1 C17 ? bmst000242 1 3 covalent SING O2 C7 ? bmst000242 1 4 covalent SING O2 H19 ? bmst000242 1 5 covalent SING N3 C13 ? bmst000242 1 6 covalent SING N3 H20 ? bmst000242 1 7 covalent SING N3 H21 ? bmst000242 1 8 covalent SING N4 C9 ? bmst000242 1 9 covalent SING N4 C15 ? bmst000242 1 10 covalent DOUB N4 C17 ? bmst000242 1 11 covalent SING N5 C12 ? bmst000242 1 12 covalent DOUB N5 C13 ? bmst000242 1 13 covalent DOUB N6 C12 ? bmst000242 1 14 covalent SING N6 C18 ? bmst000242 1 15 covalent SING C7 C8 ? bmst000242 1 16 covalent SING C7 H22 ? bmst000242 1 17 covalent SING C7 H23 ? bmst000242 1 18 covalent SING C8 C14 ? bmst000242 1 19 covalent SING C8 H24 ? bmst000242 1 20 covalent SING C8 H25 ? bmst000242 1 21 covalent SING C9 C16 ? bmst000242 1 22 covalent SING C9 H26 ? bmst000242 1 23 covalent SING C9 H27 ? bmst000242 1 24 covalent SING C10 C12 ? bmst000242 1 25 covalent SING C10 H28 ? bmst000242 1 26 covalent SING C10 H29 ? bmst000242 1 27 covalent SING C10 H30 ? bmst000242 1 28 covalent SING C11 C15 ? bmst000242 1 29 covalent SING C11 H31 ? bmst000242 1 30 covalent SING C11 H32 ? bmst000242 1 31 covalent SING C11 H33 ? bmst000242 1 32 covalent SING C13 C16 ? bmst000242 1 33 covalent DOUB C14 C15 ? bmst000242 1 34 covalent DOUB C16 C18 ? bmst000242 1 35 covalent SING C17 H34 ? bmst000242 1 36 covalent SING C18 H35 ? bmst000242 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 no PubChem 3668 sid ? Thiamin ? 'matching entry' ? bmst000242 1 no PubChem 1130 cid ? Thiamin ? 'matching entry' ? bmst000242 1 no KEGG C00378 'compound ID' ? Thiamin ? 'matching entry' ? bmst000242 1 no ChemIDplus *na ? ? Thiamin ? 'matching entry' ? bmst000242 1 no 'CAS Registry' 59-43-8 'registry number' ? Thiamin ? 'matching entry' ? bmst000242 1 stop_ loop_ _Chem_comp_citation.Citation_ID _Chem_comp_citation.Citation_label _Chem_comp_citation.Entry_ID _Chem_comp_citation.Comp_ID 1 $citations bmst000242 1 stop_ save_ ############################ # Computer software used # ############################ save_software_1 _Software.Sf_category software _Software.Sf_framecode software_1 _Software.Entry_ID bmst000242 _Software.ID 1 _Software.Name Gaussian _Software.Version ? _Software.Details ? loop_ _Vendor.Name _Vendor.Address _Vendor.Electronic_address _Vendor.Entry_ID _Vendor.Software_ID 'Gaussian, Inc.' ? http://www.gaussian.com/home.htm bmst000242 1 stop_ loop_ _Task.Task _Task.Entry_ID _Task.Software_ID 'geometry optimization' bmst000242 1 'chemical shift calculation' bmst000242 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 bmst000242 _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.Entry_ID _Chem_shift_ref.Chem_shift_reference_ID H 1 TMS 'methyl protons' ppm 0.00 na direct ? bmst000242 1 C 13 TMS 'methyl carbons' ppm 0.00 na direct ? bmst000242 1 N 15 'ammonia pentamer' nitrogen ppm 0.00 na direct ? bmst000242 1 P 31 'phosphoric acid' phosphorus ppm 0.00 na direct ? bmst000242 1 stop_ save_ save_chem_shifts_calc_type _Chem_shifts_calc_type.Sf_category chem_shifts_calc_type _Chem_shifts_calc_type.Sf_framecode chem_shifts_calc_type _Chem_shifts_calc_type.Entry_ID bmst000242 _Chem_shifts_calc_type.ID 1 _Chem_shifts_calc_type.Calculation_level 'Density Functional Theory' _Chem_shifts_calc_type.Quantum_mechanical_method GIAO _Chem_shifts_calc_type.Quantum_mechanical_theory_level B3LYP _Chem_shifts_calc_type.Quantum_mechanical_basis_set 3-21g** _Chem_shifts_calc_type.Chem_shift_nucleus ? _Chem_shifts_calc_type.Chem_shift_reference_ID 1 _Chem_shifts_calc_type.Chem_shift_reference_label $chem_shift_reference _Chem_shifts_calc_type.Details ; Theoretical Chemical shift referencing and correction: 1H chemical shifts Tetramethylsilane (TMS) was geometry optimized at the B3LYP/6-311+g* level of theory. The chemical shielding of TMS was calculated at the pbe1pbe/3-21g* level of theory using the GIAO method. The chemical shielding of TMS was used as the reference (0 ppm) to obtain all other chemical shifts. A series of small organic molecules were optimized and the chemical shieldings were calculated in the same manner as that for TMS. To correct for biases arising from the applied level of theory, especially the bias from the small basis set size, a linear regression analysis was used. The slope and intercept from this regression was used to correct the calculated chemical shifts. The chemical shift was calculated by subtracting the chemical shielding value of the compound of interest from that of TMS and applying the slope and intercept corrections obtained from the regression analysis. corrected_shift=((TMS_shielding - uncorrected_shielding)+1.006)/0.963 13C chemical shifts: Tetramethylsilane (TMS) was geometry optimized at the B3LYP/6-311+g* level of theory. The chemical shielding of TMS was calculated at the pbe1pbe/3-21g* level of theory using the GIAO method. The chemical shielding of TMS was used as the reference (0 ppm) to obtain all other chemical shifts. A series of small organic molecules were optimized and the chemical shieldings were calculated in the same manner as that for TMS. To correct for biases arising from the applied level of theory, especially the bias from the small basis set size, a linear regression analysis of theoretical versus experimental chemical shifts was used. The slope and intercept from this regression was used to correct the calculated chemical shifts. The chemical shift was calculated by subtracting the chemical shielding value of the compound of interest from that of TMS and applying the slope and intercept corrections obtained from the regression analysis. Corrected_shift=((TMS_shielding - uncorrected shielding) -4.53)/0.85 15N chemical shifts: A cyclic pentamer of ammonia (NH3_5) was geometry optimized at the B3LYP/6-311+g* level of theory. The chemical shielding of NH3_5 was calculated at the pbe1pbe/3-21g* level of theory using the GIAO method. The chemical shielding of NH3_5 was used as the reference (0 ppm) to obtain all other chemical shifts. A series of small organic molecules were optimized and the chemical shieldings were calculated in the same manner as that for NH3_5. To correct for biases arising from the applied level of theory, especially the bias from the small basis set size, a linear regression analysis was used. The slope and intercept from this regression was used to correct the calculated chemical shifts. The chemical shift was calculated by subtracting the chemical shielding value of the compound of interest from that of NH3_5 and applying the slope and intercept corrections obtained from the regression analysis. Corrected_shift=((NH_3_5_shielding - uncorrected_shielding)+10.2)/0.9088 31P chemical shifts: Phosphoric acid (H3PO4) was geometry optimized at the B3LYP/6-311+g* level of theory. The chemical shielding of H3PO4 was calculated at the pbe1pbe/3-21g* level of theory using the GIAO method. The chemical shielding of H3PO4 was used as the reference (0 ppm) to obtain all other chemical shifts. No correction for linear bias or offset was applied to calculated 31P chemical shifts. The chemical shift was calculated by subtracting the chemical shielding value of the compound of interest from that of H3PO4. Shift=(H3PO4_shielding - shielding) ; loop_ _Chem_shifts_calc_software.Software_ID _Chem_shifts_calc_software.Software_label _Chem_shifts_calc_software.Entry_ID _Chem_shifts_calc_software.Chem_shifts_calc_type_ID 1 $software_1 bmst000242 1 stop_ save_ ################################# # Theoretical chemical shifts # ################################# save_theoretical_chem_shifts _Theoretical_chem_shift_list.Sf_category theoretical_chem_shifts _Theoretical_chem_shift_list.Sf_framecode theoretical_chem_shifts _Theoretical_chem_shift_list.Entry_ID bmst000242 _Theoretical_chem_shift_list.ID 1 _Theoretical_chem_shift_list.Chem_shifts_calc_type_ID 1 _Theoretical_chem_shift_list.Chem_shifts_calc_type_label $chem_shifts_calc_type _Theoretical_chem_shift_list.Model_atomic_coordinates_ID 1 _Theoretical_chem_shift_list.Model_atomic_coordinates_label $conformer_family_coord_set_1 _Theoretical_chem_shift_list.Fermi_contact_spin_density_units ? _Theoretical_chem_shift_list.Chem_shift_1H_err ? _Theoretical_chem_shift_list.Chem_shift_2H_err ? _Theoretical_chem_shift_list.Chem_shift_13C_err ? _Theoretical_chem_shift_list.Chem_shift_15N_err ? _Theoretical_chem_shift_list.Chem_shift_19F_err ? _Theoretical_chem_shift_list.Chem_shift_31P_err ? _Theoretical_chem_shift_list.Details ? _Theoretical_chem_shift_list.Text_data_format ? _Theoretical_chem_shift_list.Text_data ? loop_ _Theoretical_chem_shift.ID _Theoretical_chem_shift.Entity_assembly_ID _Theoretical_chem_shift.Entity_ID _Theoretical_chem_shift.Comp_index_ID _Theoretical_chem_shift.Comp_ID _Theoretical_chem_shift.Atom_ID _Theoretical_chem_shift.Atom_type _Theoretical_chem_shift.Fermi_contact_spin_density _Theoretical_chem_shift.Val _Theoretical_chem_shift.Val_err _Theoretical_chem_shift.Auth_seq_ID _Theoretical_chem_shift.Auth_comp_ID _Theoretical_chem_shift.Auth_atom_ID _Theoretical_chem_shift.Entry_ID _Theoretical_chem_shift.Theoretical_chem_shift_list_ID 1 1 1 1 1 N3 N ? 83.750 ? Thiamin ? ? bmst000242 1 2 1 1 1 1 N4 N ? 231.300 ? Thiamin ? ? bmst000242 1 3 1 1 1 1 N5 N ? 281.229 ? Thiamin ? ? bmst000242 1 4 1 1 1 1 N6 N ? 307.034 ? Thiamin ? ? bmst000242 1 5 1 1 1 1 C7 C ? 68.143 ? Thiamin ? ? bmst000242 1 6 1 1 1 1 C8 C ? 32.677 ? Thiamin ? ? bmst000242 1 7 1 1 1 1 C9 C ? 58.045 ? Thiamin ? ? bmst000242 1 8 1 1 1 1 C10 C ? 27.804 ? Thiamin ? ? bmst000242 1 9 1 1 1 1 C11 C ? 12.160 ? Thiamin ? ? bmst000242 1 10 1 1 1 1 C12 C ? 184.767 ? Thiamin ? ? bmst000242 1 11 1 1 1 1 C13 C ? 166.873 ? Thiamin ? ? bmst000242 1 12 1 1 1 1 C14 C ? 153.363 ? Thiamin ? ? bmst000242 1 13 1 1 1 1 C15 C ? 153.527 ? Thiamin ? ? bmst000242 1 14 1 1 1 1 C16 C ? 107.674 ? Thiamin ? ? bmst000242 1 15 1 1 1 1 C17 C ? 162.203 ? Thiamin ? ? bmst000242 1 16 1 1 1 1 C18 C ? 164.277 ? Thiamin ? ? bmst000242 1 17 1 1 1 1 H19 H ? 1.162 ? Thiamin ? ? bmst000242 1 18 1 1 1 1 H20 H ? 5.599 ? Thiamin ? ? bmst000242 1 19 1 1 1 1 H21 H ? 4.739 ? Thiamin ? ? bmst000242 1 20 1 1 1 1 H22 H ? 4.925 ? Thiamin ? ? bmst000242 1 21 1 1 1 1 H23 H ? 4.894 ? Thiamin ? ? bmst000242 1 22 1 1 1 1 H24 H ? 4.364 ? Thiamin ? ? bmst000242 1 23 1 1 1 1 H25 H ? 4.487 ? Thiamin ? ? bmst000242 1 24 1 1 1 1 H26 H ? 6.319 ? Thiamin ? ? bmst000242 1 25 1 1 1 1 H27 H ? 6.372 ? Thiamin ? ? bmst000242 1 26 1 1 1 1 H28 H ? 4.198 ? Thiamin ? ? bmst000242 1 27 1 1 1 1 H29 H ? 4.442 ? Thiamin ? ? bmst000242 1 28 1 1 1 1 H30 H ? 3.799 ? Thiamin ? ? bmst000242 1 29 1 1 1 1 H31 H ? 3.208 ? Thiamin ? ? bmst000242 1 30 1 1 1 1 H32 H ? 3.964 ? Thiamin ? ? bmst000242 1 31 1 1 1 1 H33 H ? 4.004 ? Thiamin ? ? bmst000242 1 32 1 1 1 1 H34 H ? 10.252 ? Thiamin ? ? bmst000242 1 33 1 1 1 1 H35 H ? 9.247 ? Thiamin ? ? bmst000242 1 stop_ save_ ##################################### # Conformer family coordinate set # ##################################### save_conformer_family_coord_set_1 _Conformer_family_coord_set.Sf_category conformer_family_coord_set _Conformer_family_coord_set.Sf_framecode conformer_family_coord_set_1 _Conformer_family_coord_set.Entry_ID bmst000242 _Conformer_family_coord_set.ID 1 _Conformer_family_coord_set.Details ? loop_ _Conformer_family_software.Software_ID _Conformer_family_software.Software_label _Conformer_family_software.Entry_ID _Conformer_family_software.Conformer_family_coord_set_ID 1 $software_1 bmst000242 1 stop_ loop_ _Atom_site.Model_ID _Atom_site.ID _Atom_site.Label_entity_assembly_ID _Atom_site.Label_entity_ID _Atom_site.Label_comp_index_ID _Atom_site.Label_comp_ID _Atom_site.Label_atom_ID _Atom_site.Auth_seq_ID _Atom_site.Auth_comp_ID _Atom_site.Auth_atom_ID _Atom_site.Type_symbol _Atom_site.Cartn_x _Atom_site.Cartn_y _Atom_site.Cartn_z _Atom_site.Entry_ID _Atom_site.Conformer_family_coord_set_ID 1 1 1 1 1 1 S1 1 1 S1 S -1.109 -2.732 1.588 bmst000242 1 1 2 1 1 1 1 O2 1 1 O2 O 3.035 -4.399 -0.112 bmst000242 1 1 3 1 1 1 1 N3 1 1 N3 N 0.412 3.654 0.657 bmst000242 1 1 4 1 1 1 1 N4 1 1 N4 N -0.850 -0.236 1.336 bmst000242 1 1 5 1 1 1 1 N5 1 1 N5 N 0.031 3.369 -1.599 bmst000242 1 1 6 1 1 1 1 N6 1 1 N6 N -1.360 1.647 -2.488 bmst000242 1 1 7 1 1 1 1 C7 1 1 C7 C 1.886 -3.587 -0.205 bmst000242 1 1 8 1 1 1 1 C8 1 1 C8 C 1.673 -3.018 1.210 bmst000242 1 1 9 1 1 1 1 C9 1 1 C9 C -1.213 1.216 1.263 bmst000242 1 1 10 1 1 1 1 C10 1 1 C10 C -0.259 3.194 -4.006 bmst000242 1 1 11 1 1 1 1 C11 1 1 C11 C 1.611 0.189 0.940 bmst000242 1 1 12 1 1 1 1 C12 1 1 C12 C -0.535 2.709 -2.613 bmst000242 1 1 13 1 1 1 1 C13 1 1 C13 C -0.209 2.946 -0.349 bmst000242 1 1 14 1 1 1 1 C14 1 1 C14 C 0.496 -2.094 1.316 bmst000242 1 1 15 1 1 1 1 C15 1 1 C15 C 0.455 -0.728 1.197 bmst000242 1 1 16 1 1 1 1 C16 1 1 C16 C -1.000 1.798 -0.109 bmst000242 1 1 17 1 1 1 1 C17 1 1 C17 C -1.768 -1.174 1.545 bmst000242 1 1 18 1 1 1 1 C18 1 1 C18 C -1.568 1.219 -1.247 bmst000242 1 1 19 1 1 1 1 H19 1 1 H19 H 3.215 -4.794 -0.979 bmst000242 1 1 20 1 1 1 1 H20 1 1 H20 H 0.870 4.493 0.317 bmst000242 1 1 21 1 1 1 1 H21 1 1 H21 H -0.089 3.801 1.523 bmst000242 1 1 22 1 1 1 1 H22 1 1 H22 H 0.995 -4.159 -0.513 bmst000242 1 1 23 1 1 1 1 H23 1 1 H23 H 2.014 -2.760 -0.922 bmst000242 1 1 24 1 1 1 1 H24 1 1 H24 H 1.566 -3.857 1.905 bmst000242 1 1 25 1 1 1 1 H25 1 1 H25 H 2.584 -2.486 1.506 bmst000242 1 1 26 1 1 1 1 H26 1 1 H26 H -2.255 1.272 1.593 bmst000242 1 1 27 1 1 1 1 H27 1 1 H27 H -0.605 1.719 2.018 bmst000242 1 1 28 1 1 1 1 H28 1 1 H28 H 0.029 2.357 -4.649 bmst000242 1 1 29 1 1 1 1 H29 1 1 H29 H -1.172 3.624 -4.435 bmst000242 1 1 30 1 1 1 1 H30 1 1 H30 H 0.525 3.953 -4.002 bmst000242 1 1 31 1 1 1 1 H31 1 1 H31 H 1.646 0.495 -0.111 bmst000242 1 1 32 1 1 1 1 H32 1 1 H32 H 1.563 1.100 1.544 bmst000242 1 1 33 1 1 1 1 H33 1 1 H33 H 2.547 -0.321 1.174 bmst000242 1 1 34 1 1 1 1 H34 1 1 H34 H -2.817 -0.949 1.680 bmst000242 1 1 35 1 1 1 1 H35 1 1 H35 H -2.218 0.348 -1.150 bmst000242 1 stop_ save_