5-Aminosalicylic acid (CED0002522)

Record Information
Version1.0
Creation Date2016-05-22 03:50:20 UTC
Update Date2026-05-14 16:24:54 UTC
Accession NumberCHEM016980
Identification
Common Name5-Aminosalicylic acid
ClassSmall Molecule
Description
5-Aminosalicylic acid is an organic compound with the formula C7H7NO3 and an average molecular weight of 153.14 g/mol. 5-Aminosalicylic acid belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is utilized as an intestinal antiinflammatory agent within the category of healthcare, pharmaceuticals, and veterinary products. The compound is found in or released from 22 recorded sources. These include drinking water and water supply, ceilings in building and construction, and food, food processing and cookware, specifically in the preparation of malt, food preservation, and fermentation processes for beer. It is also associated with household cleaning and consumer products, such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is linked to electrical and electronic equipment, including electrodes, fixed capacitors and their manufacture, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices, among 4 other sources. Recorded exposure routes for the substance are rectal and oral. At the molecular level, 5-Aminosalicylic acid interacts with 7 recorded protein targets. It acts as an agonist or inhibitor of Prostaglandin G/H synthase 1 (PTGS1) and Prostaglandin G/H synthase 2 (PTGS2). Other protein targets include Peroxisome proliferator-activated receptor gamma (PPARG), Inhibitor of nuclear factor kappa-B kinase subunit alpha (CHUK), and 3 other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
3-Carboxy-4-hydroxyanilineChEBI
5-Aminosalicylic acidChEBI
5-ASAChEBI
AsacolChEBI
AsacolitinChEBI
CanasaChEBI
ClaversalChEBI
FisalamineChEBI
IialdaChEBI
LixacolChEBI
m-Aminosalicylic acidChEBI
MesalazinaChEBI
MesalazinumChEBI
MesasalChEBI
p-AminosalicylsaeureChEBI
PentasaChEBI
RowasaChEBI
SalofalkChEBI
AprisoKegg
DelzicolKegg
LialdaKegg
SfrowasaKegg
5-AminosalicylateGenerator
m-AminosalicylateGenerator
MesalamineHMDB
5 Aminosalicylic acidHMDB
Antigen brand OF mesalamineHMDB
Henning berlin brand OF mesalamineHMDB
Hydrochloride, mesalamineHMDB
Norgine brand OF mesalamineHMDB
Procter and gamble brand OF mesalamineHMDB
Sanofi synthelabo brand OF mesalamineHMDB
m Aminosalicylic acidHMDB
Meta aminosalicylic acidHMDB
Byk brand OF mesalamineHMDB
GlaxoSmithKline brand OF mesalamineHMDB
Mesalamine hydrochlorideHMDB
Monosodium salt, mesalamineHMDB
Novo 5 asaHMDB
Provalis brand OF mesalamineHMDB
Schering plough brand OF mesalamineHMDB
Yamanouchi brand OF mesalamineHMDB
5 AminosalicylateHMDB
AsacolonHMDB
AscolitinHMDB
Axcan brand OF mesalamineHMDB
Celltech brand OF mesalamineHMDB
Falk brand OF mesalamineHMDB
Ferring brand OF mesalamineHMDB
Merckle brand OF mesalamineHMDB
Novo5 asaHMDB
Novopharm brand OF mesalamineHMDB
Allphar brand OF mesalamineHMDB
Farmasa brand OF mesalamineHMDB
FivasaHMDB
Mesalamine monosodium saltHMDB
Novo-5 asaHMDB
Schering-plough brand OF mesalamineHMDB
SmithKline brand OF mesalamineHMDB
Solvay brand OF mesalamineHMDB
Meta-aminosalicylic acidHMDB
MesalazineChEBI
Chemical FormulaC7H7NO3
Average Molecular Mass153.135 g/mol
Monoisotopic Mass153.043 g/mol
CAS Registry Number89-57-6
IUPAC Name5-amino-2-hydroxybenzoic acid
Traditional Namemesalazine
SMILESNC1=CC(C(O)=O)=C(O)C=C1
InChI IdentifierInChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
InChI KeyKBOPZPXVLCULAV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • Salicylic acid
  • Benzoic acid
  • P-aminophenol
  • Aminophenol
  • Benzoyl
  • Aniline or substituted anilines
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.2 g/LALOGPS
logP0.75ALOGPS
logP-0.29ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.02ChemAxon
pKa (Strongest Basic)5.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0zg0-1900000000-8c59ef73371ab7058ab9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05fr-6290000000-8c65a0e3aa600dc402bbNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0900000000-db75ae2d436dd6156c91Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-31f47e60332bc9d52dc5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a59-4900000000-e694f0e584d434cd6c19Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a5i-5900000000-5e487b4d3f15751bc421Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0il0-9000000000-65d9d31a1ef145800998Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-afe56677019b761236caNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0900000000-e6285983e501467965c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-f9d037b61fba1f9bc003Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pbi-0900000000-8692528b7d752229a174Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-057i-9300000000-b6f08e642ac27344075cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-0900000000-ff6f4a59111a55871916Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-b2691ada23e4712099eeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-7900000000-cb7f7dfff58bf74b852aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-4d1e5c8d16c81a250fccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-875d8abd6f6773a40634Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-9700000000-b6a77be3dfe8ecfbaf8eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-e04ca92dcfe7d4857011Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-1900000000-34d228a18521111a48cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9200000000-b4371439ac0a5b3d574aNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2680.0Log mg/kg[1500:4800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
258Intestinal antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
5 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureHTH-type transcriptional regulator MgrAP0C1S0Staphylococcus aureusPredicted (SEA)0.0778492
Click to view 3D structure2-Hydroxyacid oxidase 1Q9WU19Mus musculusPredicted (SEA)0.0778492
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)15.8034
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)57.4527
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)52.4704
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)10.1204
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)59.399
Hepatocyte nuclear factor 4-gamma structureClick to view 3D structureHepatocyte nuclear factor 4-gammaQ14541HumansPredicted (SEA)0.311397
Thiosulfate sulfurtransferase structureClick to view 3D structureThiosulfate sulfurtransferaseQ16762HumansPredicted (SEA)0.0778492
Hepatocyte nuclear factor 4-alpha structureClick to view 3D structureHepatocyte nuclear factor 4-alphaP41235HumansPredicted (SEA)0.856341
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)114.905
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)37.7569
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)71.9327
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)51.8476
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)54.3388
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)489.282
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)29.6606
Lysine-specific demethylase 4E structureClick to view 3D structureLysine-specific demethylase 4EB2RXH2HumansPredicted (SEA)6.85073
Click to view 3D structureD-aspartate oxidaseQ922Z0Mus musculusPredicted (SEA)0.389246
Click to view 3D structureD-aspartate oxidaseD3ZDM7Rattus norvegicusPredicted (SEA)0.389246
3-hydroxyanthranilate 3,4-dioxygenase structureClick to view 3D structure3-hydroxyanthranilate 3,4-dioxygenaseP46952HumansPredicted (SEA)0.0778492
Click to view 3D structure3-hydroxyanthranilate 3,4-dioxygenaseP46953Rattus norvegicusPredicted (SEA)0.0778492
Nicotinate phosphoribosyltransferase structureClick to view 3D structureNicotinate phosphoribosyltransferaseQ6XQN6HumansPredicted (SEA)1.40129
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansPredicted (SEA)16.7376
Stromal cell-derived factor 1 structureClick to view 3D structureStromal cell-derived factor 1P48061HumansPredicted (SEA)6.85073
Concentrations
Not Available
External Links
DrugBank IDDB00244
HMDB IDHMDB0014389
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-12711
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMesalamine
Chemspider ID3933
ChEBI ID6775
PubChem Compound ID4075
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Wikipedia: http://en.wikipedia.org/wiki/Mesalamine
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10648473
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22304735
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22648999
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23137838
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23146664
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23302220
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217