data_bmst000199 save_entry_information _Entry.Sf_category entry_information _Entry.Sf_framecode entry_information _Entry.ID bmst000199 _Entry.Title N_acetyl_D_glucosamine_1_phosphate _Entry.Version_type update _Entry.Submission_date 2006-02-23 _Entry.Accession_date 2006-02-23 _Entry.Last_release_date 2011-09-14 _Entry.Original_release_date 2006-02-23 _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 N_acetyl_D_glucosamine_1_phosphate 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. ? bmst000199 2 John Markley L. ? bmst000199 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 bmst000199 stop_ loop_ _Data_set.Type _Data_set.Count _Data_set.Entry_ID other_data_list 1 bmst000199 stop_ loop_ _Datum.Type _Datum.Count _Datum.Entry_ID "theoretical chemical shifts" 1 bmst000199 stop_ loop_ _Release.Release_number _Release.Date _Release.Submission_date _Release.Type _Release.Author _Release.Detail _Release.Entry_ID 1 2006-02-23 2006-02-23 original BMRB "Original theoretical calculations from NMRFAM" bmst000199 2 2008-11-18 2008-11-18 update BMRB "updated the file to match latest NMR STAR dictionary" bmst000199 3 2008-11-25 2008-11-25 update BMRB "fixed enumerations: N should be no" bmst000199 4 2010-09-16 2010-09-16 update BMRB "Removed Shielding_tensor_list_ID and Shielding_tensor_list_label from theoretical_chem_shifts" bmst000199 5 2011-09-14 2011-09-14 update BMRB "Partially brought up to date with latest Dictionary" bmst000199 stop_ save_ save_citations _Citation.Sf_category citations _Citation.Sf_framecode citations _Citation.Entry_ID bmst000199 _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. ? bmst000199 1 2 T. Barrett T. ? ? bmst000199 1 3 D. Benson D. A. ? bmst000199 1 4 S. Bryant S. H. ? bmst000199 1 5 K. Canese K. ? ? bmst000199 1 6 V. Chetvenin V. ? ? bmst000199 1 7 D. Church D. M. ? bmst000199 1 8 M. DiCuccio M. ? ? bmst000199 1 9 R. Edgar R. ? ? bmst000199 1 10 S. Federhen S. ? ? bmst000199 1 11 L. Geer L. Y. ? bmst000199 1 12 W. Helmberg W. ? ? bmst000199 1 13 Y. Kapustin Y. ? ? bmst000199 1 14 D. Kenton D. L. ? bmst000199 1 15 O. Khovayko O. ? ? bmst000199 1 16 D. Lipman D. J. ? bmst000199 1 17 T. Madden T. L. ? bmst000199 1 18 D. Maglott D. R. ? bmst000199 1 19 J. Ostell J. ? ? bmst000199 1 20 K. Pruitt K. D. ? bmst000199 1 21 G. Schuler G. D. ? bmst000199 1 22 L. Schriml L. M. ? bmst000199 1 23 E. Sequeira E. ? ? bmst000199 1 24 S. Sherry S. T. ? bmst000199 1 25 K. Sirotkin K. ? ? bmst000199 1 26 A. Souvorov A. ? ? bmst000199 1 27 G. Starchenko G. ? ? bmst000199 1 28 T. Suzek T. O. ? bmst000199 1 29 R. Tatusov R. ? ? bmst000199 1 30 T. Tatusova T. A. ? bmst000199 1 31 L. Bagner L. ? ? bmst000199 1 32 E. Yaschenko E. ? ? bmst000199 1 stop_ save_ save_assembly _Assembly.Sf_category assembly _Assembly.Sf_framecode assembly _Assembly.Entry_ID bmst000199 _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 $N_acetyl_D_glucosamine_1_phosphate yes native no no ? ? ? bmst000199 1 stop_ save_ save_N_acetyl_D_glucosamine_1_phosphate _Entity.Sf_category entity _Entity.Sf_framecode N_acetyl_D_glucosamine_1_phosphate _Entity.Entry_ID bmst000199 _Entity.ID 1 _Entity.BMRB_code ? _Entity.Name 'N-Acetyl-alpha-D-glucosamine 1-phosphate' _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 bmst000199 1 stop_ save_ save_chem_comp_1 _Chem_comp.Sf_category chem_comp _Chem_comp.Sf_framecode chem_comp_1 _Chem_comp.Entry_ID bmst000199 _Chem_comp.ID 1 _Chem_comp.Provenance PubChem _Chem_comp.Name 'N-Acetyl-alpha-D-glucosamine 1-phosphate' _Chem_comp.Type non-polymer _Chem_comp.BMRB_code ? _Chem_comp.PDB_code ? _Chem_comp.InCHi_code ; InChI=1/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/f/h9,14-15H ; _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 no _Chem_comp.Formula 'C8 H16 N O9 P' _Chem_comp.Formula_weight 301.1877010000 _Chem_comp.Formula_mono_iso_wt_nat 301.056267628 _Chem_comp.Formula_mono_iso_wt_13C 309.08310633 _Chem_comp.Formula_mono_iso_wt_15N 302.053302521 _Chem_comp.Formula_mono_iso_wt_13C_15N 309.08310633 _Chem_comp.Image_file_name standards/N_acetyl_D_glucosamine_1_phosphate/lit/6921.png _Chem_comp.Image_file_format png _Chem_comp.Topo_file_name ? _Chem_comp.Topo_file_format ? _Chem_comp.Struct_file_name standards/N_acetyl_D_glucosamine_1_phosphate/lit/6921.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 C04501 synonym bmst000199 1 N-acetyl-glucosamine-1-phosphate synonym bmst000199 1 "N-Acetyl-alpha-D-glucosamine 1-phosphate" synonym bmst000199 1 N-ACETYL-D-GLUCOSAMINE-1-P synonym bmst000199 1 "N-Acetyl-D-glucosamine 1-phosphate" synonym bmst000199 1 "N-acetyl-D-glucosamine 1-phosphate" synonym bmst000199 1 "N-acetyl-alpha-D-glucosamine 1-phosphate" synonym bmst000199 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 "[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid" IUPAC bmst000199 1 "(3-acetamido-4,5-dihydroxy-6-methylol-tetrahydropyran-2-yl)oxyphosphonic acid" IUPAC_TRADITIONAL bmst000199 1 "[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphosphonic acid" IUPAC_CAS bmst000199 1 "[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphosphonic acid" IUPAC_OPENEYE bmst000199 1 "[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid" IUPAC_SYSTEMATIC bmst000199 1 stop_ loop_ _Chem_comp_SMILES.Type _Chem_comp_SMILES.String _Chem_comp_SMILES.Entry_ID _Chem_comp_SMILES.Comp_ID Isomeric CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)O)CO)O)O bmst000199 1 Canonical CC(=O)NC1C(C(C(OC1OP(=O)(O)O)CO)O)O bmst000199 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.Entry_ID _Chem_comp_atom.Comp_ID C1 C ? ? ? ? 6.0010 0.8100 -1.367 0.571 0.139 bmst000199 1 C2 C ? ? ? ? 5.1350 0.3100 -0.078 -0.189 0.457 bmst000199 1 C3 C ? ? ? ? 6.8671 0.3100 -1.196 2.025 0.657 bmst000199 1 N4 N ? ? ? ? 6.0010 1.8100 -1.699 0.527 -1.265 bmst000199 1 O5 O ? ? ? ? 5.1350 -0.6900 1.030 0.444 -0.183 bmst000199 1 O6 O ? ? ? ? 4.2690 0.8100 -0.127 -1.501 -0.029 bmst000199 1 C7 C ? ? ? ? 6.8671 -0.6900 0.109 2.678 0.162 bmst000199 1 O8 O ? ? ? ? 7.7331 0.8100 -1.136 2.060 2.084 bmst000199 1 C9 C ? ? ? ? 5.1350 2.3100 -2.882 0.001 -1.711 bmst000199 1 C10 C ? ? ? ? 6.0010 -1.1900 1.332 1.747 0.310 bmst000199 1 P11 P ? ? ? ? 3.4030 0.3100 1.224 -2.428 0.063 bmst000199 1 O12 O ? ? ? ? 7.7331 -1.1900 -0.117 2.990 -1.212 bmst000199 1 C13 C ? ? ? ? 5.1350 3.3100 -3.033 -0.054 -3.222 bmst000199 1 O14 O ? ? ? ? 4.2690 1.8100 -3.751 -0.412 -0.951 bmst000199 1 C15 C ? ? ? ? 6.0010 -2.1900 1.935 1.704 1.719 bmst000199 1 O16 O ? ? ? ? 2.5369 -0.1900 0.600 -3.776 0.690 bmst000199 1 O17 O ? ? ? ? 2.9030 1.1760 2.034 -1.854 1.322 bmst000199 1 O18 O ? ? ? ? 3.9030 -0.5560 1.941 -2.623 -1.214 bmst000199 1 O19 O ? ? ? ? 5.1350 -2.6900 2.998 0.743 1.681 bmst000199 1 H20 H ? ? ? ? 6.5380 1.1200 -2.208 0.100 0.659 bmst000199 1 H21 H ? ? ? ? 5.1350 0.9300 0.077 -0.204 1.542 bmst000199 1 H22 H ? ? ? ? 7.4040 -0.0000 -2.031 2.629 0.280 bmst000199 1 H23 H ? ? ? ? 6.5380 2.1200 -1.022 0.902 -1.914 bmst000199 1 H24 H ? ? ? ? 7.4040 -0.3800 0.268 3.595 0.750 bmst000199 1 H25 H ? ? ? ? 8.2700 0.5000 -1.976 1.717 2.426 bmst000199 1 H26 H ? ? ? ? 5.4641 -1.5000 2.124 2.101 -0.362 bmst000199 1 H27 H ? ? ? ? 7.7331 -1.8100 0.694 3.381 -1.573 bmst000199 1 H28 H ? ? ? ? 5.7550 3.3100 -4.059 0.216 -3.485 bmst000199 1 H29 H ? ? ? ? 5.1350 3.9300 -2.862 -1.083 -3.556 bmst000199 1 H30 H ? ? ? ? 4.5150 3.3100 -2.335 0.602 -3.752 bmst000199 1 H31 H ? ? ? ? 6.2131 -2.7726 2.325 2.702 1.963 bmst000199 1 H32 H ? ? ? ? 6.6116 -2.0823 1.186 1.442 2.473 bmst000199 1 H33 H ? ? ? ? 2.0000 0.1200 0.869 -4.528 0.139 bmst000199 1 H34 H ? ? ? ? 2.2830 1.1760 2.428 -0.958 1.181 bmst000199 1 H35 H ? ? ? ? 5.1350 -3.3100 3.363 0.655 2.575 bmst000199 1 stop_ loop_ _Atom_nomenclature.Atom_ID _Atom_nomenclature.Atom_name _Atom_nomenclature.Naming_system _Atom_nomenclature.Entry_ID _Atom_nomenclature.Comp_ID C1 C1 ? bmst000199 1 C2 C2 ? bmst000199 1 C3 C3 ? bmst000199 1 N4 N4 ? bmst000199 1 O5 O5 ? bmst000199 1 O6 O6 ? bmst000199 1 C7 C7 ? bmst000199 1 O8 O8 ? bmst000199 1 C9 C9 ? bmst000199 1 C10 C10 ? bmst000199 1 P11 P11 ? bmst000199 1 O12 O12 ? bmst000199 1 C13 C13 ? bmst000199 1 O14 O14 ? bmst000199 1 C15 C15 ? bmst000199 1 O16 O16 ? bmst000199 1 O17 O17 ? bmst000199 1 O18 O18 ? bmst000199 1 O19 O19 ? bmst000199 1 H20 H20 ? bmst000199 1 H21 H21 ? bmst000199 1 H22 H22 ? bmst000199 1 H23 H23 ? bmst000199 1 H24 H24 ? bmst000199 1 H25 H25 ? bmst000199 1 H26 H26 ? bmst000199 1 H27 H27 ? bmst000199 1 H28 H28 ? bmst000199 1 H29 H29 ? bmst000199 1 H30 H30 ? bmst000199 1 H31 H31 ? bmst000199 1 H32 H32 ? bmst000199 1 H33 H33 ? bmst000199 1 H34 H34 ? bmst000199 1 H35 H35 ? bmst000199 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 C1 C2 ? bmst000199 1 2 covalent SING C1 C3 ? bmst000199 1 3 covalent SING C1 N4 ? bmst000199 1 4 covalent SING C1 H20 ? bmst000199 1 5 covalent SING C2 O5 ? bmst000199 1 6 covalent SING C2 O6 ? bmst000199 1 7 covalent SING C2 H21 ? bmst000199 1 8 covalent SING C3 C7 ? bmst000199 1 9 covalent SING C3 O8 ? bmst000199 1 10 covalent SING C3 H22 ? bmst000199 1 11 covalent SING N4 C9 ? bmst000199 1 12 covalent SING N4 H23 ? bmst000199 1 13 covalent SING O5 C10 ? bmst000199 1 14 covalent SING O6 P11 ? bmst000199 1 15 covalent SING C7 C10 ? bmst000199 1 16 covalent SING C7 O12 ? bmst000199 1 17 covalent SING C7 H24 ? bmst000199 1 18 covalent SING O8 H25 ? bmst000199 1 19 covalent SING C9 C13 ? bmst000199 1 20 covalent DOUB C9 O14 ? bmst000199 1 21 covalent SING C10 C15 ? bmst000199 1 22 covalent SING C10 H26 ? bmst000199 1 23 covalent SING P11 O16 ? bmst000199 1 24 covalent SING P11 O17 ? bmst000199 1 25 covalent DOUB P11 O18 ? bmst000199 1 26 covalent SING O12 H27 ? bmst000199 1 27 covalent SING C13 H28 ? bmst000199 1 28 covalent SING C13 H29 ? bmst000199 1 29 covalent SING C13 H30 ? bmst000199 1 30 covalent SING C15 O19 ? bmst000199 1 31 covalent SING C15 H31 ? bmst000199 1 32 covalent SING C15 H32 ? bmst000199 1 33 covalent SING O16 H33 ? bmst000199 1 34 covalent SING O17 H34 ? bmst000199 1 35 covalent SING O19 H35 ? bmst000199 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 2964 sid ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 1 no PubChem 7115 sid ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 1 no PubChem 6921 sid ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 1 no PubChem 900 cid ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 1 no PubChem 440364 cid ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 1 no PubChem 440272 cid ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 1 no KEGG C04256 "compound ID" ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 1 no "CAS Registry" 31281-59-1 "registry number" ? "N-Acetyl-alpha-D-glucosamine 1-phosphate" ? "matching entry" ? bmst000199 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 bmst000199 1 stop_ save_ save_software_1 _Software.Sf_category software _Software.Sf_framecode software_1 _Software.Entry_ID bmst000199 _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 bmst000199 1 stop_ loop_ _Task.Task _Task.Entry_ID _Task.Software_ID "geometry optimization" bmst000199 1 "chemical shift calculation" bmst000199 1 stop_ save_ 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 bmst000199 _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 ? bmst000199 1 C 13 TMS "methyl carbons" ppm 0.00 na direct ? bmst000199 1 N 15 "ammonia pentamer" nitrogen ppm 0.00 na direct ? bmst000199 1 P 31 "phosphoric acid" phosphorus ppm 0.00 na direct ? bmst000199 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 bmst000199 _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 bmst000199 1 stop_ save_ 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 bmst000199 _Theoretical_chem_shift_list.ID 1 _Theoretical_chem_shift_list.Data_file_name N_acetyl_D_glucosamine_1_phosphate_6921.g03.shifts _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 C1 C ? 50.101 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 2 1 1 1 1 C2 C ? 95.933 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 3 1 1 1 1 C3 C ? 78.338 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 4 1 1 1 1 N4 N ? 118.935 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 5 1 1 1 1 C7 C ? 71.756 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 6 1 1 1 1 C9 C ? 173.614 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 7 1 1 1 1 C10 C ? 86.403 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 8 1 1 1 1 P11 P ? 4.704 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 9 1 1 1 1 C13 C ? 23.665 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 10 1 1 1 1 C15 C ? 61.653 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 11 1 1 1 1 H20 H ? 5.138 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 12 1 1 1 1 H21 H ? 6.477 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 13 1 1 1 1 H22 H ? 4.974 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 14 1 1 1 1 H23 H ? 6.792 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 15 1 1 1 1 H24 H ? 4.373 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 16 1 1 1 1 H25 H ? 0.705 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 17 1 1 1 1 H26 H ? 5.131 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 18 1 1 1 1 H27 H ? 0.333 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 19 1 1 1 1 H28 H ? 2.981 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 20 1 1 1 1 H29 H ? 3.501 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 21 1 1 1 1 H30 H ? 2.534 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 22 1 1 1 1 H31 H ? 4.442 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 23 1 1 1 1 H32 H ? 5.926 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 24 1 1 1 1 H33 H ? 3.621 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 25 1 1 1 1 H34 H ? 7.861 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 26 1 1 1 1 H35 H ? 0.982 ? N_acetyl_D_glucosamine_1_phosphate ? ? bmst000199 1 stop_ save_ 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 bmst000199 _Conformer_family_coord_set.ID 1 _Conformer_family_coord_set.File_name N_acetyl_D_glucosamine_1_phosphate_6921_opt.pdb _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 bmst000199 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 C1 1 1 C1 C -1.367 0.571 0.139 bmst000199 1 1 2 1 1 1 1 C2 1 1 C2 C -0.078 -0.189 0.457 bmst000199 1 1 3 1 1 1 1 C3 1 1 C3 C -1.196 2.025 0.657 bmst000199 1 1 4 1 1 1 1 N4 1 1 N4 N -1.699 0.527 -1.265 bmst000199 1 1 5 1 1 1 1 O5 1 1 O5 O 1.030 0.444 -0.183 bmst000199 1 1 6 1 1 1 1 O6 1 1 O6 O -0.127 -1.501 -0.029 bmst000199 1 1 7 1 1 1 1 C7 1 1 C7 C 0.109 2.678 0.162 bmst000199 1 1 8 1 1 1 1 O8 1 1 O8 O -1.136 2.060 2.084 bmst000199 1 1 9 1 1 1 1 C9 1 1 C9 C -2.882 0.001 -1.711 bmst000199 1 1 10 1 1 1 1 C10 1 1 C10 C 1.332 1.747 0.310 bmst000199 1 1 11 1 1 1 1 P11 1 1 P11 P 1.224 -2.428 0.063 bmst000199 1 1 12 1 1 1 1 O12 1 1 O12 O -0.117 2.990 -1.212 bmst000199 1 1 13 1 1 1 1 C13 1 1 C13 C -3.033 -0.054 -3.222 bmst000199 1 1 14 1 1 1 1 O14 1 1 O14 O -3.751 -0.412 -0.951 bmst000199 1 1 15 1 1 1 1 C15 1 1 C15 C 1.935 1.704 1.719 bmst000199 1 1 16 1 1 1 1 O16 1 1 O16 O 0.600 -3.776 0.690 bmst000199 1 1 17 1 1 1 1 O17 1 1 O17 O 2.034 -1.854 1.322 bmst000199 1 1 18 1 1 1 1 O18 1 1 O18 O 1.941 -2.623 -1.214 bmst000199 1 1 19 1 1 1 1 O19 1 1 O19 O 2.998 0.743 1.681 bmst000199 1 1 20 1 1 1 1 H20 1 1 H20 H -2.208 0.100 0.659 bmst000199 1 1 21 1 1 1 1 H21 1 1 H21 H 0.077 -0.204 1.542 bmst000199 1 1 22 1 1 1 1 H22 1 1 H22 H -2.031 2.629 0.280 bmst000199 1 1 23 1 1 1 1 H23 1 1 H23 H -1.022 0.902 -1.914 bmst000199 1 1 24 1 1 1 1 H24 1 1 H24 H 0.268 3.595 0.750 bmst000199 1 1 25 1 1 1 1 H25 1 1 H25 H -1.976 1.717 2.426 bmst000199 1 1 26 1 1 1 1 H26 1 1 H26 H 2.124 2.101 -0.362 bmst000199 1 1 27 1 1 1 1 H27 1 1 H27 H 0.694 3.381 -1.573 bmst000199 1 1 28 1 1 1 1 H28 1 1 H28 H -4.059 0.216 -3.485 bmst000199 1 1 29 1 1 1 1 H29 1 1 H29 H -2.862 -1.083 -3.556 bmst000199 1 1 30 1 1 1 1 H30 1 1 H30 H -2.335 0.602 -3.752 bmst000199 1 1 31 1 1 1 1 H31 1 1 H31 H 2.325 2.702 1.963 bmst000199 1 1 32 1 1 1 1 H32 1 1 H32 H 1.186 1.442 2.473 bmst000199 1 1 33 1 1 1 1 H33 1 1 H33 H 0.869 -4.528 0.139 bmst000199 1 1 34 1 1 1 1 H34 1 1 H34 H 2.428 -0.958 1.181 bmst000199 1 1 35 1 1 1 1 H35 1 1 H35 H 3.363 0.655 2.575 bmst000199 1 stop_ save_