You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2017-12-07 01:46:47 UTC
HMDB IDHMDB0001972
Secondary Accession Numbers
  • HMDB01972
Metabolite Identification
Common Name3-Aminosalicylic acid
Description3-aminosalicylic acid, also known as 3-amino-2-hydroxy-benzoate or desacetyleupaserrin, is a member of the class of compounds known as aminosalicylic acids. Aminosalicylic acids are salicylic acids carrying an amino group on the benzene ring. 3-aminosalicylic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 3-aminosalicylic acid can be found primarily in blood and urine. Aminosalicylic acid can refer to any amino derivative of salicylic acid, such as: 3-Aminosalicylic acid 4-Aminosalicylic acid (para-aminosalicylic acid, PAS) 5-Aminosalicylic acid (mesalazine) 6-Aminosalicylic acid (Wikipedia). 3-Aminosalicylic acid is a derivative of salicylic acid, a common anti-inflammatory drug..
Structure
Thumb
Synonyms
ValueSource
3-amino SalicylateHMDB
3-amino Salicylic acidHMDB
3-amino-(8CI)salicylateHMDB
3-amino-(8CI)salicylic acidHMDB
3-amino-2-Hydroxy-(9ci)benzoateHMDB
3-amino-2-Hydroxy-(9ci)benzoic acidHMDB
3-amino-2-Hydroxy-benzoateHMDB
3-amino-2-Hydroxy-benzoic acidHMDB
3-amino-2-HydroxybenzoateHMDB
3-amino-2-Hydroxybenzoic acidHMDB
3-amino-SalicylateHMDB
3-amino-Salicylic acidHMDB
3-AminosalicylateHMDB
DesacetyleupaserrinHMDB
ParasalHMDB
PaserHMDB
Chemical FormulaC7H7NO3
Average Molecular Weight153.1354
Monoisotopic Molecular Weight153.042593095
IUPAC Name3-amino-2-hydroxybenzoic acid
Traditional Name3-aminosalicylic acid
CAS Registry Number570-23-0
SMILES
NC1=CC=CC(C(O)=O)=C1O
InChI Identifier
InChI=1S/C7H7NO3/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,9H,8H2,(H,10,11)
InChI KeyIQGMRVWUTCYCST-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aminosalicylic acids. These are salicylic acids carrying an amino group on the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAminosalicylic acids
Alternative Parents
Substituents
  • 3-aminosalicylic acid
  • Aminosalicylic acid
  • Salicylic acid
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Aniline or substituted anilines
  • O-aminophenol
  • Aminophenol
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Primary aromatic amine
  • Vinylogous acid
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP0.84ALOGPS
logP0.27ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)4.17ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-3900000000-4d7141e8d15281687d8aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-5090000000-cda2ecb81897c8c26786View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-d5138de5f78a38530939View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053u-9500000000-9f53b1a2a70325e64659View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03e9-9000000000-429051a65e5f48060734View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-8425e1c663c71cc511d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-172aee9b7359303e10c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4r-9100000000-950800697f9bff7289f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-aa836fb2fc67f63db233View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-58071ddcf3a0740544caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-17de825134e6f524833bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.032 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022771
    KNApSAcK IDNot Available
    Chemspider ID61723
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6409
    PubChem Compound68443
    PDB ID1CW
    ChEBI ID1162549
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General ReferencesNot Available

    Only showing the first 10 proteins. There are 41 proteins in total.

    Enzymes

    General function:
    Involved in acetyltransferase activity
    Specific function:
    Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
    Gene Name:
    NAT1
    Uniprot ID:
    P18440
    Molecular weight:
    33898.445
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
    Gene Name:
    NAT2
    Uniprot ID:
    P11245
    Molecular weight:
    33570.245
    General function:
    Involved in hydrolase activity
    Specific function:
    Arylacetamide deacetylation is an important enzyme activity in the metabolic activation of arylamine substrates to ultimate carcinogens. Displays major serine hydrolase activity in liver microsomes. Hydrolyzes also flutamide, which is an antiandrogen drug used for the treatment of prostate cancer that occasionally causes severe hepatotoxicity. Displays cellular triglyceride lipase activity in liver. Increases intracellular fatty acids derived from hydrolysis of newly formed triglyceride stores.
    Gene Name:
    AADAC
    Uniprot ID:
    P22760
    Molecular weight:
    45733.28
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6T7
    Molecular weight:
    33570.2
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6T8
    Molecular weight:
    33572.3
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6T9
    Molecular weight:
    33542.2
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6U4
    Molecular weight:
    33542.2
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6U6
    Molecular weight:
    33574.3
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6U7
    Molecular weight:
    33528.2
    General function:
    Involved in acetyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    NAT2
    Uniprot ID:
    A4Z6U9
    Molecular weight:
    33530.2

    Only showing the first 10 proteins. There are 41 proteins in total.