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Record Information
Version3.6
Creation Date2013-06-15 17:46:47 UTC
Update Date2016-02-11 08:09:07 UTC
HMDB IDHMDB60602
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-acetyl-5-aminosalicylic acid
DescriptionN-acetyl-5-aminosalicylic acid is a metabolite of mesalazine. Mesalazine, also known as mesalamine or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammatory bowel disease, such as ulcerative colitis and mild-to-moderate Crohn's disease. Mesalazine is a bowel-specific aminosalicylate drug that acts locally in the gut and has its predominant actions there, thereby having few systemic side effects. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC9H9NO4
Average Molecular Weight195.1721
Monoisotopic Molecular Weight195.053157781
IUPAC Name5-acetamido-2-hydroxybenzoic acid
Traditional Name5-acetamido-2-hydroxybenzoic acid
CAS Registry Number51-59-2
SMILES
CC(=O)NC1=CC=C(O)C(=C1)C(O)=O
InChI Identifier
InChI=1S/C9H9NO4/c1-5(11)10-6-2-3-8(12)7(4-6)9(13)14/h2-4,12H,1H3,(H,10,11)(H,13,14)
InChI KeyInChIKey=GEFDRROBUCULOD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-arylamide
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Acetanilide
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Phenol
  • Acetamide
  • Vinylogous acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.93 mg/mLALOGPS
logP1.4ALOGPS
logP1.21ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.62ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.16 m3·mol-1ChemAxon
Polarizability18.56 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00924
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60602
Metagene LinkHMDB60602
METLIN IDNot Available
PubChem Compound65512
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available