data_HIS
#
_chem_comp.id HIS
_chem_comp.name HISTIDINE
_chem_comp.type "L-PEPTIDE LINKING"
_chem_comp.pdbx_type ATOMP
_chem_comp.formula "C6 H10 N3 O2"
_chem_comp.mon_nstd_parent_comp_id ?
_chem_comp.pdbx_synonyms ?
_chem_comp.pdbx_formal_charge 1
_chem_comp.pdbx_initial_date 1999-07-08
_chem_comp.pdbx_modified_date 2023-11-03
_chem_comp.pdbx_ambiguous_flag N
_chem_comp.pdbx_release_status REL
_chem_comp.pdbx_replaced_by ?
_chem_comp.pdbx_replaces ?
_chem_comp.formula_weight 156.162
_chem_comp.one_letter_code H
_chem_comp.three_letter_code HIS
_chem_comp.pdbx_model_coordinates_details ?
_chem_comp.pdbx_model_coordinates_missing_flag N
_chem_comp.pdbx_ideal_coordinates_details "OpenEye/OEToolkits V1.4.2"
_chem_comp.pdbx_ideal_coordinates_missing_flag N
_chem_comp.pdbx_model_coordinates_db_code ?
_chem_comp.pdbx_subcomponent_list ?
_chem_comp.pdbx_processing_site EBI
#
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.alt_atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.charge
_chem_comp_atom.pdbx_align
_chem_comp_atom.pdbx_aromatic_flag
_chem_comp_atom.pdbx_leaving_atom_flag
_chem_comp_atom.pdbx_stereo_config
_chem_comp_atom.pdbx_backbone_atom_flag
_chem_comp_atom.pdbx_n_terminal_atom_flag
_chem_comp_atom.pdbx_c_terminal_atom_flag
_chem_comp_atom.model_Cartn_x
_chem_comp_atom.model_Cartn_y
_chem_comp_atom.model_Cartn_z
_chem_comp_atom.pdbx_model_Cartn_x_ideal
_chem_comp_atom.pdbx_model_Cartn_y_ideal
_chem_comp_atom.pdbx_model_Cartn_z_ideal
_chem_comp_atom.pdbx_component_atom_id
_chem_comp_atom.pdbx_component_comp_id
_chem_comp_atom.pdbx_ordinal
HIS N N N 0 1 N N N Y Y N 33.472 42.685 -4.610 -0.040 -1.210 0.053 N HIS 1
HIS CA CA C 0 1 N N S Y N N 33.414 41.686 -5.673 1.172 -1.709 0.652 CA HIS 2
HIS C C C 0 1 N N N Y N Y 33.773 42.279 -7.040 1.083 -3.207 0.905 C HIS 3
HIS O O O 0 1 N N N Y N Y 33.497 43.444 -7.337 0.040 -3.770 1.222 O HIS 4
HIS CB CB C 0 1 N N N N N N 32.005 41.080 -5.734 1.484 -0.975 1.962 CB HIS 5
HIS CG CG C 0 1 Y N N N N N 31.888 39.902 -6.651 2.940 -1.060 2.353 CG HIS 6
HIS ND1 ND1 N 1 1 Y N N N N N 32.539 38.710 -6.414 3.380 -2.075 3.129 ND1 HIS 7
HIS CD2 CD2 C 0 1 Y N N N N N 31.199 39.734 -7.804 3.960 -0.251 2.046 CD2 HIS 8
HIS CE1 CE1 C 0 1 Y N N N N N 32.251 37.857 -7.382 4.693 -1.908 3.317 CE1 HIS 9
HIS NE2 NE2 N 0 1 Y N N N N N 31.439 38.453 -8.237 5.058 -0.801 2.662 NE2 HIS 10
HIS OXT OXT O 0 1 N Y N Y N Y 34.382 41.455 -7.879 2.247 -3.882 0.744 OXT HIS 11
HIS H H H 0 1 N N N Y Y N 33.485 42.227 -3.721 -0.102 -1.155 -0.950 H HIS 12
HIS H2 HN2 H 0 1 N Y N Y Y N 34.301 43.234 -4.714 -0.715 -0.741 0.634 H2 HIS 13
HIS HA HA H 0 1 N N N Y N N 34.155 40.908 -5.439 1.965 -1.558 -0.089 HA HIS 14
HIS HB2 1HB H 0 1 N N N N N N 31.733 40.750 -4.721 1.215 0.087 1.879 HB2 HIS 15
HIS HB3 2HB H 0 1 N N N N N N 31.337 41.860 -6.127 0.859 -1.368 2.775 HB3 HIS 16
HIS HD1 HD1 H 0 1 N N N N N N 33.135 38.521 -5.633 2.828 -2.838 3.511 HD1 HIS 17
HIS HD2 HD2 H 0 1 N N N N N N 30.577 40.470 -8.292 4.108 0.647 1.479 HD2 HIS 18
HIS HE1 HE1 H 0 1 N N N N N N 32.618 36.844 -7.461 5.340 -2.550 3.892 HE1 HIS 19
HIS HE2 HE2 H 0 1 N N N N N N 31.061 38.039 -9.065 6.002 -0.428 2.627 HE2 HIS 20
HIS HXT HXT H 0 1 N Y N Y N Y 34.553 41.905 -8.698 2.188 -4.848 0.901 HXT HIS 21
#
loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.value_order
_chem_comp_bond.pdbx_aromatic_flag
_chem_comp_bond.pdbx_stereo_config
_chem_comp_bond.pdbx_ordinal
HIS N CA SING N N 1
HIS N H SING N N 2
HIS N H2 SING N N 3
HIS CA C SING N N 4
HIS CA CB SING N N 5
HIS CA HA SING N N 6
HIS C O DOUB N N 7
HIS C OXT SING N N 8
HIS CB CG SING N N 9
HIS CB HB2 SING N N 10
HIS CB HB3 SING N N 11
HIS CG ND1 SING Y N 12
HIS CG CD2 DOUB Y N 13
HIS ND1 CE1 DOUB Y N 14
HIS ND1 HD1 SING N N 15
HIS CD2 NE2 SING Y N 16
HIS CD2 HD2 SING N N 17
HIS CE1 NE2 SING Y N 18
HIS CE1 HE1 SING N N 19
HIS NE2 HE2 SING N N 20
HIS OXT HXT SING N N 21
#
loop_
_pdbx_chem_comp_descriptor.comp_id
_pdbx_chem_comp_descriptor.type
_pdbx_chem_comp_descriptor.program
_pdbx_chem_comp_descriptor.program_version
_pdbx_chem_comp_descriptor.descriptor
HIS SMILES ACDLabs 10.04 O=C(O)C(N)Cc1cnc[nH+]1
HIS SMILES_CANONICAL CACTVS 3.341 N[C@@H](Cc1c[nH]c[nH+]1)C(O)=O
HIS SMILES CACTVS 3.341 N[CH](Cc1c[nH]c[nH+]1)C(O)=O
HIS SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1c([nH+]c[nH]1)C[C@@H](C(=O)O)N
HIS SMILES "OpenEye OEToolkits" 1.5.0 c1c([nH+]c[nH]1)CC(C(=O)O)N
HIS InChI InChI 1.03 InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/p+1/t5-/m0/s1
HIS InChIKey InChI 1.03 HNDVDQJCIGZPNO-YFKPBYRVSA-O
#
loop_
_pdbx_chem_comp_identifier.comp_id
_pdbx_chem_comp_identifier.type
_pdbx_chem_comp_identifier.program
_pdbx_chem_comp_identifier.program_version
_pdbx_chem_comp_identifier.identifier
HIS "SYSTEMATIC NAME" ACDLabs 10.04 3-(1H-imidazol-3-ium-4-yl)-L-alanine
HIS "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2S)-2-amino-3-(1H-imidazol-3-ium-4-yl)propanoic acid"
#
loop_
_pdbx_chem_comp_audit.comp_id
_pdbx_chem_comp_audit.action_type
_pdbx_chem_comp_audit.date
_pdbx_chem_comp_audit.processing_site
HIS 'Create component' 1999-07-08 EBI
HIS 'Modify descriptor' 2011-06-04 RCSB
HIS 'Modify backbone' 2023-11-03 PDBE
#
loop_
_software.name
_software.version
_software.description
rdkit 2023.09.6 'Core functionality.'
pdbeccdutils 0.8.6 'Wrapper to provide 2D templates and molecular fragments.'
#
loop_
_pdbe_chem_comp_atom_depiction.comp_id
_pdbe_chem_comp_atom_depiction.atom_id
_pdbe_chem_comp_atom_depiction.element
_pdbe_chem_comp_atom_depiction.model_Cartn_x
_pdbe_chem_comp_atom_depiction.model_Cartn_y
_pdbe_chem_comp_atom_depiction.pdbx_ordinal
HIS N N 3.884 -0.523 1
HIS CA C 5.311 -0.059 2
HIS C C 5.623 1.408 3
HIS O O 4.508 2.411 4
HIS CB C 6.426 -1.063 5
HIS CG C 7.852 -0.600 6
HIS ND1 N 9.066 -1.481 7
HIS CD2 C 8.316 0.827 8
HIS CE1 C 10.280 -0.600 9
HIS NE2 N 9.816 0.827 10
HIS OXT O 7.050 1.871 11
#
loop_
_pdbe_chem_comp_bond_depiction.comp_id
_pdbe_chem_comp_bond_depiction.atom_id_1
_pdbe_chem_comp_bond_depiction.atom_id_2
_pdbe_chem_comp_bond_depiction.value_order
_pdbe_chem_comp_bond_depiction.bond_dir
_pdbe_chem_comp_bond_depiction.pdbx_ordinal
HIS CA N SINGLE BEGINDASH 1
HIS CA C SINGLE NONE 2
HIS CA CB SINGLE NONE 3
HIS C O DOUBLE NONE 4
HIS C OXT SINGLE NONE 5
HIS CB CG SINGLE NONE 6
HIS CG ND1 SINGLE NONE 7
HIS CG CD2 DOUBLE NONE 8
HIS ND1 CE1 DOUBLE NONE 9
HIS CD2 NE2 SINGLE NONE 10
HIS CE1 NE2 SINGLE NONE 11
#
loop_
_pdbe_chem_comp_substructure.comp_id
_pdbe_chem_comp_substructure.substructure_name
_pdbe_chem_comp_substructure.id
_pdbe_chem_comp_substructure.substructure_type
_pdbe_chem_comp_substructure.substructure_smiles
_pdbe_chem_comp_substructure.substructure_inchis
_pdbe_chem_comp_substructure.substructure_inchikeys
HIS MurckoScaffold S1 scaffold 'c1c[nH+]c[nH]1' InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)/p+1 RAXXELZNTBOGNW-UHFFFAOYSA-O
HIS imidazole F1 fragment 'c1c[nH]cn1' InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) RAXXELZNTBOGNW-UHFFFAOYSA-N
HIS peptide F2 fragment NCC=O InChI=1S/C2H5NO/c3-1-2-4/h2H,1,3H2 LYIIBVSRGJSHAV-UHFFFAOYSA-N
#
loop_
_pdbe_chem_comp_substructure_mapping.comp_id
_pdbe_chem_comp_substructure_mapping.atom_id
_pdbe_chem_comp_substructure_mapping.substructure_id
_pdbe_chem_comp_substructure_mapping.substructure_ordinal
HIS CG S1 1
HIS ND1 S1 1
HIS CD2 S1 1
HIS CE1 S1 1
HIS NE2 S1 1
HIS CG F1 1
HIS CD2 F1 1
HIS NE2 F1 1
HIS CE1 F1 1
HIS ND1 F1 1
HIS O F2 1
HIS C F2 1
HIS CA F2 1
HIS N F2 1
#
_pdbe_chem_comp_rdkit_properties.comp_id HIS
_pdbe_chem_comp_rdkit_properties.exactmw 156.077
_pdbe_chem_comp_rdkit_properties.amw 156.165
_pdbe_chem_comp_rdkit_properties.lipinskiHBA 5
_pdbe_chem_comp_rdkit_properties.lipinskiHBD 5
_pdbe_chem_comp_rdkit_properties.NumRotatableBonds 4
_pdbe_chem_comp_rdkit_properties.NumHBD 3
_pdbe_chem_comp_rdkit_properties.NumHBA 3
_pdbe_chem_comp_rdkit_properties.NumHeavyAtoms 11
_pdbe_chem_comp_rdkit_properties.NumAtoms 21
_pdbe_chem_comp_rdkit_properties.NumHeteroatoms 5
_pdbe_chem_comp_rdkit_properties.NumAmideBonds 0
_pdbe_chem_comp_rdkit_properties.FractionCSP3 0.333
_pdbe_chem_comp_rdkit_properties.NumRings 1
_pdbe_chem_comp_rdkit_properties.NumAromaticRings 1
_pdbe_chem_comp_rdkit_properties.NumAliphaticRings 0
_pdbe_chem_comp_rdkit_properties.NumSaturatedRings 0
_pdbe_chem_comp_rdkit_properties.NumHeterocycles 1
_pdbe_chem_comp_rdkit_properties.NumAromaticHeterocycles 1
_pdbe_chem_comp_rdkit_properties.NumSaturatedHeterocycles 0
_pdbe_chem_comp_rdkit_properties.NumAliphaticHeterocycles 0
_pdbe_chem_comp_rdkit_properties.NumSpiroAtoms 0
_pdbe_chem_comp_rdkit_properties.NumBridgeheadAtoms 0
_pdbe_chem_comp_rdkit_properties.NumAtomStereoCenters 1
_pdbe_chem_comp_rdkit_properties.NumUnspecifiedAtomStereoCenters 0
_pdbe_chem_comp_rdkit_properties.labuteASA 77.619
_pdbe_chem_comp_rdkit_properties.tpsa 93.250
_pdbe_chem_comp_rdkit_properties.CrippenClogP -1.272
_pdbe_chem_comp_rdkit_properties.CrippenMR 36.398
_pdbe_chem_comp_rdkit_properties.chi0v 5.158
_pdbe_chem_comp_rdkit_properties.chi1v 2.526
_pdbe_chem_comp_rdkit_properties.chi2v 0.804
_pdbe_chem_comp_rdkit_properties.chi3v 0.804
_pdbe_chem_comp_rdkit_properties.chi4v 0.397
_pdbe_chem_comp_rdkit_properties.chi0n 15.158
_pdbe_chem_comp_rdkit_properties.chi1n 7.223
_pdbe_chem_comp_rdkit_properties.chi2n 0.804
_pdbe_chem_comp_rdkit_properties.chi3n 0.804
_pdbe_chem_comp_rdkit_properties.chi4n 0.397
_pdbe_chem_comp_rdkit_properties.hallKierAlpha -1.360
_pdbe_chem_comp_rdkit_properties.kappa1 1.866
_pdbe_chem_comp_rdkit_properties.kappa2 3.157
_pdbe_chem_comp_rdkit_properties.kappa3 2.047
_pdbe_chem_comp_rdkit_properties.Phi 0.535
#
loop_
_pdbe_chem_comp_external_mappings.comp_id
_pdbe_chem_comp_external_mappings.source
_pdbe_chem_comp_external_mappings.resource
_pdbe_chem_comp_external_mappings.resource_id
HIS UniChem ChEBI 32513
HIS UniChem PubChem 5288559
HIS UniChem PubChem 86580368
HIS UniChem Nikkaji J1.218.634G
HIS UniChem MetaboLights MTBLC32513
HIS UniChem CCDC BEZPIH
HIS UniChem Nikkaji J2.296.405D
HIS UniChem PubChem 5460943
HIS UniChem Nikkaji J1.918.540K
#
loop_
_pdbe_chem_comp_rdkit_conformer.comp_id
_pdbe_chem_comp_rdkit_conformer.atom_id
_pdbe_chem_comp_rdkit_conformer.Cartn_x_rdkit
_pdbe_chem_comp_rdkit_conformer.Cartn_y_rdkit
_pdbe_chem_comp_rdkit_conformer.Cartn_z_rdkit
_pdbe_chem_comp_rdkit_conformer.rdkit_method
_pdbe_chem_comp_rdkit_conformer.rdkit_ordinal
HIS N -1.160 -0.138 -1.484 ETKDGv3 1
HIS CA -1.247 -0.529 -0.074 ETKDGv3 2
HIS C -2.672 -0.459 0.408 ETKDGv3 3
HIS O -3.251 -1.502 0.815 ETKDGv3 4
HIS CB -0.347 0.368 0.792 ETKDGv3 5
HIS CG 1.095 0.226 0.405 ETKDGv3 6
HIS ND1 1.746 1.025 -0.577 ETKDGv3 7
HIS CD2 1.926 -0.710 0.841 ETKDGv3 8
HIS CE1 2.945 0.557 -0.688 ETKDGv3 9
HIS NE2 3.172 -0.551 0.176 ETKDGv3 10
HIS OXT -3.353 0.754 0.403 ETKDGv3 11
HIS H -1.749 -0.792 -2.050 ETKDGv3 12
HIS H2 -1.555 0.824 -1.606 ETKDGv3 13
HIS HA -0.889 -1.579 0.022 ETKDGv3 14
HIS HB2 -0.648 1.433 0.682 ETKDGv3 15
HIS HB3 -0.464 0.093 1.863 ETKDGv3 16
HIS HD1 1.345 1.826 -1.114 ETKDGv3 17
HIS HD2 1.700 -1.485 1.562 ETKDGv3 18
HIS HE1 3.684 0.957 -1.369 ETKDGv3 19
HIS HE2 4.034 -1.132 0.271 ETKDGv3 20
HIS HXT -4.312 0.813 0.725 ETKDGv3 21
#