data_SAL
#
_chem_comp.id SAL
_chem_comp.name '2-HYDROXYBENZOIC ACID'
_chem_comp.type NON-POLYMER
_chem_comp.pdbx_type HETAIN
_chem_comp.formula 'C7 H6 O3'
_chem_comp.mon_nstd_parent_comp_id ?
_chem_comp.pdbx_synonyms 'SALICYLIC ACID'
_chem_comp.pdbx_formal_charge 0
_chem_comp.pdbx_initial_date 1999-07-08
_chem_comp.pdbx_modified_date 2024-09-27
_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 138.121
_chem_comp.one_letter_code ?
_chem_comp.three_letter_code SAL
_chem_comp.pdbx_model_coordinates_details ?
_chem_comp.pdbx_model_coordinates_missing_flag N
_chem_comp.pdbx_ideal_coordinates_details ?
_chem_comp.pdbx_ideal_coordinates_missing_flag N
_chem_comp.pdbx_model_coordinates_db_code 1FO4
_chem_comp.pdbx_subcomponent_list ?
_chem_comp.pdbx_processing_site PDBJ
_chem_comp.pdbx_pcm Y
#
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
SAL "C1'" "C1'" C 0 1 N N N N N N 73.041 -6.580 39.637 0.226 0.006 1.635 "C1'" SAL 1
SAL "O1'" "O1'" O 0 1 N N N N N N 74.080 -7.031 39.173 -0.837 0.018 2.222 "O1'" SAL 2
SAL "O2'" "O2'" O 0 1 N N N N N N 72.831 -6.884 40.805 1.379 -0.007 2.332 "O2'" SAL 3
SAL C1 C1 C 0 1 Y N N N N N 72.138 -5.766 38.890 0.255 0.005 0.161 C1 SAL 4
SAL C2 C2 C 0 1 Y N N N N N 72.341 -5.396 37.534 -0.941 0.012 -0.567 C2 SAL 5
SAL C3 C3 C 0 1 Y N N N N N 71.427 -4.584 36.794 -0.902 0.018 -1.953 C3 SAL 6
SAL C4 C4 C 0 1 Y N N N N N 70.267 -4.132 37.444 0.311 0.003 -2.611 C4 SAL 7
SAL C5 C5 C 0 1 Y N N N N N 69.995 -4.459 38.795 1.497 -0.010 -1.894 C5 SAL 8
SAL C6 C6 C 0 1 Y N N N N N 70.939 -5.277 39.504 1.477 -0.009 -0.517 C6 SAL 9
SAL O2 O2 O 0 1 N N N N N N 73.433 -5.793 36.840 -2.133 0.027 0.080 O2 SAL 10
SAL "HO2'" "'HO2" H 0 0 N N N N N N 72.024 -6.534 41.165 1.360 -0.006 3.299 "HO2'" SAL 11
SAL H3 H3 H 0 1 N N N N N N 71.613 -4.311 35.741 -1.821 0.029 -2.519 H3 SAL 12
SAL H4 H4 H 0 1 N N N N N N 69.553 -3.506 36.881 0.337 0.002 -3.691 H4 SAL 13
SAL H5 H5 H 0 1 N N N N N N 69.076 -4.088 39.280 2.442 -0.021 -2.418 H5 SAL 14
SAL H6 H6 H 0 1 N N N N N N 70.736 -5.538 40.556 2.404 -0.019 0.037 H6 SAL 15
SAL HO2 HO2 H 0 1 N N N N N N 73.568 -5.545 35.932 -2.392 -0.895 0.209 HO2 SAL 16
#
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
SAL "C1'" "O1'" DOUB N N 1
SAL "C1'" "O2'" SING N N 2
SAL "C1'" C1 SING N N 3
SAL "O2'" "HO2'" SING N N 4
SAL C1 C2 SING Y N 5
SAL C1 C6 DOUB Y N 6
SAL C2 C3 DOUB Y N 7
SAL C2 O2 SING N N 8
SAL C3 C4 SING Y N 9
SAL C3 H3 SING N N 10
SAL C4 C5 DOUB Y N 11
SAL C4 H4 SING N N 12
SAL C5 C6 SING Y N 13
SAL C5 H5 SING N N 14
SAL C6 H6 SING N N 15
SAL O2 HO2 SING N N 16
#
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
SAL SMILES ACDLabs 10.04 'O=C(O)c1ccccc1O'
SAL SMILES_CANONICAL CACTVS 3.341 'OC(=O)c1ccccc1O'
SAL SMILES CACTVS 3.341 'OC(=O)c1ccccc1O'
SAL SMILES_CANONICAL 'OpenEye OEToolkits' 1.5.0 'c1ccc(c(c1)C(=O)O)O'
SAL SMILES 'OpenEye OEToolkits' 1.5.0 'c1ccc(c(c1)C(=O)O)O'
SAL InChI InChI 1.03 'InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)'
SAL InChIKey InChI 1.03 YGSDEFSMJLZEOE-UHFFFAOYSA-N
#
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
SAL 'SYSTEMATIC NAME' ACDLabs 10.04 '2-hydroxybenzoic acid'
SAL 'SYSTEMATIC NAME' 'OpenEye OEToolkits' 1.5.0 '2-hydroxybenzoic 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
SAL 'Create component' 1999-07-08 PDBJ
SAL 'Modify descriptor' 2011-06-04 RCSB
SAL 'Modify synonyms' 2021-03-01 PDBE
SAL 'Modify PCM' 2024-09-27 PDBE
#
_pdbx_chem_comp_synonyms.ordinal 1
_pdbx_chem_comp_synonyms.comp_id SAL
_pdbx_chem_comp_synonyms.name 'SALICYLIC ACID'
_pdbx_chem_comp_synonyms.provenance ?
_pdbx_chem_comp_synonyms.type ?
#
_pdbx_chem_comp_pcm.pcm_id 1
_pdbx_chem_comp_pcm.comp_id SAL
_pdbx_chem_comp_pcm.modified_residue_id 4HH
_pdbx_chem_comp_pcm.type None
_pdbx_chem_comp_pcm.category 'Covalent chemical modification'
_pdbx_chem_comp_pcm.position 'Amino-acid side chain'
_pdbx_chem_comp_pcm.polypeptide_position 'Any position'
_pdbx_chem_comp_pcm.comp_id_linking_atom "C1'"
_pdbx_chem_comp_pcm.modified_residue_id_linking_atom SU
_pdbx_chem_comp_pcm.uniprot_specific_ptm_accession ?
_pdbx_chem_comp_pcm.uniprot_generic_ptm_accession ?
#
_pdbe_chem_comp_drugbank_details.comp_id SAL
_pdbe_chem_comp_drugbank_details.drugbank_id DB00936
_pdbe_chem_comp_drugbank_details.type 'small molecule'
_pdbe_chem_comp_drugbank_details.name 'Salicylic acid'
_pdbe_chem_comp_drugbank_details.description
'A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics.'
_pdbe_chem_comp_drugbank_details.cas_number 69-72-7
_pdbe_chem_comp_drugbank_details.mechanism_of_action
"Salicylic acid directly irreversibly inhibits COX-1 and COX-2 to decrease conversion of arachidonic acid to precursors of prostaglandins and thromboxanes. Salicylate's use in rheumatic diseases is due to it's analgesic and anti-inflammatory activity. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. Salicylic acid allows cells of the epidermis to more readily slough off. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid competitively inhibits oxidation of uridine-5-diphosphoglucose (UDPG) with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of the glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to a phenolic acceptor. Inhibition of mucopoly saccharide synthesis is likely responsible for the slowing of wound healing with salicylates."
#
loop_
_pdbe_chem_comp_synonyms.comp_id
_pdbe_chem_comp_synonyms.name
_pdbe_chem_comp_synonyms.provenance
_pdbe_chem_comp_synonyms.type
SAL 'SALICYLIC ACID' wwPDB ?
SAL 2-Carboxyphenol DrugBank ?
SAL '2-Hydroxybenzoic acid' DrugBank ?
SAL 'Acidum salicylicum' DrugBank ?
SAL O-carboxyphenol DrugBank ?
SAL 'O-hydroxybenzoic acid' DrugBank ?
SAL 'Salicylic acid' DrugBank ?
SAL "Dr. Scholl's Callus Removers" DrugBank 'International brand'
SAL "Dr. Scholl's Corn Removers" DrugBank 'International brand'
SAL "Dr. Scholl's Wart Remover Kit" DrugBank 'International brand'
SAL 'Duofil Wart Remover' DrugBank 'International brand'
SAL Duoplant DrugBank 'International brand'
SAL 'Ionil Plus shampoo' DrugBank 'International brand'
SAL Salonil DrugBank 'International brand'
SAL Salsonin DrugBank 'International brand'
SAL Stridex DrugBank 'International brand'
#
_pdbe_chem_comp_drugbank_classification.comp_id SAL
_pdbe_chem_comp_drugbank_classification.drugbank_id DB00936
_pdbe_chem_comp_drugbank_classification.parent 'Salicylic acids'
_pdbe_chem_comp_drugbank_classification.kingdom 'Organic compounds'
_pdbe_chem_comp_drugbank_classification.class 'Benzene and substituted derivatives'
_pdbe_chem_comp_drugbank_classification.superclass Benzenoids
_pdbe_chem_comp_drugbank_classification.description
'This compound belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.'
#
loop_
_pdbe_chem_comp_drugbank_targets.comp_id
_pdbe_chem_comp_drugbank_targets.drugbank_id
_pdbe_chem_comp_drugbank_targets.name
_pdbe_chem_comp_drugbank_targets.organism
_pdbe_chem_comp_drugbank_targets.uniprot_id
_pdbe_chem_comp_drugbank_targets.pharmacologically_active
_pdbe_chem_comp_drugbank_targets.ordinal
SAL DB00936 'Carbonic anhydrase 6' Humans P23280 yes 1
SAL DB00936 'Carbonic anhydrase 12' Humans O43570 yes 2
SAL DB00936 'Carbonic anhydrase 2' Humans P00918 yes 3
SAL DB00936 'Carbonic anhydrase 4' Humans P22748 yes 4
SAL DB00936 'Carbonic anhydrase 1' Humans P00915 yes 5
SAL DB00936 'Prostaglandin G/H synthase 1' Humans P23219 yes 6
SAL DB00936 'Prostaglandin G/H synthase 2' Humans P35354 yes 7
SAL DB00936 'Aldo-keto reductase family 1 member C1' Humans Q04828 unknown 8
#
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
SAL "C1'" C -1.430 -1.124 1
SAL "O1'" O -2.728 -0.373 2
SAL "O2'" O -1.431 -2.624 3
SAL C1 C -0.130 -0.375 4
SAL C2 C -0.129 1.125 5
SAL C3 C 1.171 1.874 6
SAL C4 C 2.469 1.123 7
SAL C5 C 2.468 -0.377 8
SAL C6 C 1.168 -1.126 9
SAL O2 O -1.427 1.876 10
#
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
SAL "C1'" "O1'" DOUBLE NONE 1
SAL "C1'" "O2'" SINGLE NONE 2
SAL "C1'" C1 SINGLE NONE 3
SAL C1 C2 DOUBLE NONE 4
SAL C1 C6 SINGLE NONE 5
SAL C2 C3 SINGLE NONE 6
SAL C2 O2 SINGLE NONE 7
SAL C3 C4 DOUBLE NONE 8
SAL C4 C5 SINGLE NONE 9
SAL C5 C6 DOUBLE NONE 10
#
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
SAL MurckoScaffold S1 scaffold c1ccccc1 InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H UHOVQNZJYSORNB-UHFFFAOYSA-N
SAL phenyl F1 fragment c1ccccc1 InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H UHOVQNZJYSORNB-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
SAL C1 S1 1
SAL C2 S1 1
SAL C3 S1 1
SAL C4 S1 1
SAL C5 S1 1
SAL C6 S1 1
SAL C1 F1 1
SAL C2 F1 1
SAL C3 F1 1
SAL C4 F1 1
SAL C5 F1 1
SAL C6 F1 1
#
_pdbe_chem_comp_rdkit_properties.comp_id SAL
_pdbe_chem_comp_rdkit_properties.exactmw 138.032
_pdbe_chem_comp_rdkit_properties.amw 138.122
_pdbe_chem_comp_rdkit_properties.lipinskiHBA 3
_pdbe_chem_comp_rdkit_properties.lipinskiHBD 2
_pdbe_chem_comp_rdkit_properties.NumRotatableBonds 2
_pdbe_chem_comp_rdkit_properties.NumHBD 2
_pdbe_chem_comp_rdkit_properties.NumHBA 3
_pdbe_chem_comp_rdkit_properties.NumHeavyAtoms 10
_pdbe_chem_comp_rdkit_properties.NumAtoms 16
_pdbe_chem_comp_rdkit_properties.NumHeteroatoms 3
_pdbe_chem_comp_rdkit_properties.NumAmideBonds 0
_pdbe_chem_comp_rdkit_properties.FractionCSP3 0
_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 0
_pdbe_chem_comp_rdkit_properties.NumAromaticHeterocycles 0
_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 0
_pdbe_chem_comp_rdkit_properties.NumUnspecifiedAtomStereoCenters 0
_pdbe_chem_comp_rdkit_properties.labuteASA 66.149
_pdbe_chem_comp_rdkit_properties.tpsa 57.530
_pdbe_chem_comp_rdkit_properties.CrippenClogP 0.573
_pdbe_chem_comp_rdkit_properties.CrippenMR 34.190
_pdbe_chem_comp_rdkit_properties.chi0v 4.725
_pdbe_chem_comp_rdkit_properties.chi1v 2.362
_pdbe_chem_comp_rdkit_properties.chi2v 0.857
_pdbe_chem_comp_rdkit_properties.chi3v 0.857
_pdbe_chem_comp_rdkit_properties.chi4v 0.445
_pdbe_chem_comp_rdkit_properties.chi0n 10.725
_pdbe_chem_comp_rdkit_properties.chi1n 5.179
_pdbe_chem_comp_rdkit_properties.chi2n 0.857
_pdbe_chem_comp_rdkit_properties.chi3n 0.857
_pdbe_chem_comp_rdkit_properties.chi4n 0.445
_pdbe_chem_comp_rdkit_properties.hallKierAlpha -1.510
_pdbe_chem_comp_rdkit_properties.kappa1 2.268
_pdbe_chem_comp_rdkit_properties.kappa2 2.390
_pdbe_chem_comp_rdkit_properties.kappa3 1.075
_pdbe_chem_comp_rdkit_properties.Phi 0.542
#
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
SAL UniChem ChEMBL CHEMBL424
SAL UniChem DrugBank DB00936
SAL UniChem 'Guide to Pharmacology' 4306
SAL UniChem 'KEGG LIGAND' C00805
SAL UniChem ChEBI 16914
SAL UniChem ZINC ZINC000000001554
SAL UniChem eMolecules 478035
SAL UniChem atlas 'salicylic acid'
SAL UniChem fdasrs O414PZ4LPZ
SAL UniChem SureChEMBL SCHEMBL16880297
SAL UniChem PharmGKB PA451299
SAL UniChem HMDB HMDB0001895
SAL UniChem NMRShiftDB 10008793
SAL UniChem LINCS LSM-4763
SAL UniChem BindingDb 26193
SAL UniChem 'EPA CompTox Dashboard' DTXSID7026368
SAL UniChem DrugCentral 2416
SAL UniChem MetaboLights MTBLC16914
SAL UniChem BRENDA 145569
SAL UniChem BRENDA 21658
SAL UniChem BRENDA 24601
SAL UniChem BRENDA 47420
SAL UniChem BRENDA 5097
SAL UniChem BRENDA 617
SAL UniChem BRENDA 765
SAL UniChem BRENDA 90999
SAL UniChem ChemicalBook CB1680010
SAL UniChem DailyMed 'SALICYLIC ACID'
SAL UniChem ClinicalTrials 'COMPOUND W'
SAL UniChem ClinicalTrials 'SALICYLIC ACID'
SAL UniChem rxnorm DUOFILM
SAL UniChem rxnorm DUOPLANT
SAL UniChem rxnorm FREEZONE
SAL UniChem rxnorm KERALYT
SAL UniChem rxnorm SALICYLATE
SAL UniChem rxnorm 'SALICYLIC ACID'
SAL UniChem rxnorm STRI-DEX
SAL UniChem MedChemExpress HY-B0167
SAL UniChem 'Probes And Drugs' PD001758
SAL UniChem CCDC SALIAC
SAL UniChem Nikkaji J2.370A
SAL UniChem SureChEMBL SCHEMBL1967
SAL UniChem 'PubChem TPHARMA' 14747739
SAL UniChem PubChem 118212070
SAL UniChem PubChem 338
SAL UniChem Mcule MCULE-8407868694
SAL UniChem ACTor 69-72-7
#
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
SAL "C1'" 1.858 0.751 0.068 ETKDGv3 1
SAL "O1'" 2.173 1.846 0.606 ETKDGv3 2
SAL "O2'" 2.836 0.001 -0.579 ETKDGv3 3
SAL C1 0.446 0.312 0.068 ETKDGv3 4
SAL C2 0.078 -0.994 0.127 ETKDGv3 5
SAL C3 -1.354 -1.357 0.018 ETKDGv3 6
SAL C4 -2.290 -0.410 -0.094 ETKDGv3 7
SAL C5 -1.901 1.011 -0.113 ETKDGv3 8
SAL C6 -0.611 1.354 -0.035 ETKDGv3 9
SAL O2 0.992 -2.032 0.323 ETKDGv3 10
SAL "HO2'" 3.801 0.311 -0.599 ETKDGv3 11
SAL H3 -1.645 -2.400 0.041 ETKDGv3 12
SAL H4 -3.335 -0.684 -0.166 ETKDGv3 13
SAL H5 -2.663 1.776 -0.196 ETKDGv3 14
SAL H6 -0.341 2.402 -0.064 ETKDGv3 15
SAL HO2 1.956 -1.886 0.593 ETKDGv3 16
#