Aminosalicylic Acid (CHEM022075)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:19:13 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022075
Identification
Common NameAminosalicylic Acid
ClassSmall Molecule
DescriptionAn aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-HYDROXY-4-aminobenzoIC ACIDChEBI
4-AminosalicylateChEBI
p-Aminosalicylic acidChEBI
Para-amino salicylic acidChEBI
PASChEBI
PaserChEBI
4-Aminosalicylic acidKegg
PamisylKegg
2-HYDROXY-4-aminobenzoateGenerator
p-AminosalicylateGenerator
Para-amino salicylateGenerator
AminosalicylateGenerator
4-ASAHMDB
Amino-pasHMDB
Aminosalicylate sodiumHMDB
APASHMDB
Para-aminosalicylic acidHMDB
PASKHMDB
4 Aminosalicylic acidHMDB
RezipasHMDB
p-Aminosalicylic acid monolithium saltHMDB
p-Aminosalicylic acid, monosodium salt, dihydrateHMDB
Acid, aminosalicylicHMDB
Alumino 4 aminosalicylic acidHMDB
p Aminosalicylic acid monolithium saltHMDB
p-Aminosalicylic acid monopotassium saltHMDB
p Aminosalicylic acidHMDB
p Aminosalicylic acid monopotassium saltHMDB
p Aminosalicylic acid monosodium saltHMDB
p-Aminosalicylic acid, aluminum (2:1) saltHMDB
Para aminosalicylic acidHMDB
Alumino-4-aminosalicylic acidHMDB
p-Aminosalicylic acid monosodium saltHMDB
p-Aminosalicylic acid, calcium (2:1) saltHMDB
Aminosalicylic acidChEBI
Chemical FormulaC7H7NO3
Average Molecular Mass153.135 g/mol
Monoisotopic Mass153.043 g/mol
CAS Registry Number65-49-6
IUPAC Name4-amino-2-hydroxybenzoic acid
Traditional Nameaminosalicylic acid
SMILESNC1=CC(O)=C(C=C1)C(O)=O
InChI IdentifierInChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
InChI KeyWUBBRNOQWQTFEX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminosalicylic acids. These are salicylic acids carrying an amino group on the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminosalicylic acids
Alternative Parents
Substituents
  • 4-aminosalicylic acid
  • Aminosalicylic acid
  • Salicylic acid
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Aniline or substituted anilines
  • M-aminophenol
  • Aminophenol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.8 g/LALOGPS
logP0.62ALOGPS
logP0.83ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-2900000000-f96d42a6d732787e860eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-2190000000-77c54a0901141e0c25ccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-3962000000-2dfafa7266e72ac813b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-9edb9b6028f854f76708Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-e893f1439cefbeef271aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-5900000000-09273d1390d26a8def2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-066r-9200000000-e029b385a8c32e95b6b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00ku-9000000000-58cccd83d40f8fade4dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-06dr-2900200000-832b5b02326d8b11bac4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-4900000000-8f56b41d56d984600d2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9000000000-de31b7181a8ba3e3c60bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-77b21d59e31f1fe41a28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-a497dd61e37afd19159fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-771daa6ebfd132e803a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9400000000-a2c0beef5eb5e0f96f27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-1900000000-f74138cc6d19303f955cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-82ef8276edc66459ee1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9500000000-347557516c4726a8670dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-7bc1a9fe6d66a88b37d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-ae2965ede5d26e091cdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-5a68b4449891b42a477dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-ffca2fee4deb986a1b34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-1900000000-ca3768868cf936ca2311Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-e1a89b3e2a6ece9b67b4Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00233
HMDB IDHMDB0014378
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDBHA
Wikipedia LinkAminosalicylic_Acid
Chemspider ID4488
ChEBI ID27565
PubChem Compound ID4649
Kegg Compound IDC02518
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11621575
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23118010
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6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25421465
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25605031
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25963985
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26004847
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26033719
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26277036
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26596566
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26848874
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27021327
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27491492
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27617928
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27671064
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=28011126
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28223391
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=28394286
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=28408267
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=28567674
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=28651968
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=28717039
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=28812999
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29. Tiitinen H, Mattila MJ: Modification of the serum isoniazid levels by different preparations of paraaminosalicylic acid. Arzneimittelforschung. 1968 May;18(5):623-5.
30. ARTIS RD, JOHNSON PK, FREE AH: A simplified test for the detection of paraaminosalicylic acid and acetylsalicylic acid metabolites in urine. Am Rev Respir Dis. 1961 Sep;84:435-9.
31. Ojo OA, Onifade A, Akande EO, Bannerman RH: The pattern of female genital tuberculosis in Ibadan. Isr J Med Sci. 1971 Feb;7(2):280-7.
32. Shah A, Panjabi C, Maurya V, Khanna P: Multidrug resistant miliary tuberculosis and Pott's disease in an immunocompetent patient. Saudi Med J. 2004 Oct;25(10):1468-70.
33. NAITO M: [Combined therapy of massive doses of isoniazid, pyrazinamide, and sulfisoxazole for patients with pulmonary tuberculosis resistant to streptomycin, paraaminosalicylic acid, and isoniazid]. Kyoto Daigaku Kekkaku Kenkyusho Kiyo. 1961 Mar;9:136-41.
34. KENDIG EL Jr, HUDGENS RO: The effect of rubeola on tuberculosis under antimicrobial therapy. II. Tuberculous meningitis treated with isoniazid, streptomycin and paraaminosalicylic acid. Pediatrics. 1959 Oct;24:619-22.
35. Joshi JV, Joshi UM, Sankolli GM, Gupta K, Rao AP, Hazari K, Sheth UK, Saxena BN: A study of interaction of a low-dose combination oral contraceptive with anti-tubercular drugs. Contraception. 1980 Jun;21(6):617-29.
36. MITROIU O, POPA M, NEGREANU W, BILCU M, POPPER M, KAUFMANN S, NICULESCU V, VANCOV Z: [The differential diagnosis of jaundices appearing during treatment with paraaminosalicylic acid (PAS) by means of serum aldolase determination]. Stud Cercet Inframicrobiol. 1960;11:125-31.
37. MILLER FF, GREEN RA: Loeffler's syndrome due to paraaminosalicylic acid. Dis Chest. 1962 Jul;42:100-3.
38. Miroshnichenko II, Sokolova GB, Mokhireva LV: [Clinical pharmacokinetics of para-aminosalicylic acid tablets]. Antibiot Khimioter. 2009;54(1-2):20-4.
39. SCHMITTOVA M, ENGELBERTH O, SRAMKOVA J: [Effect of aminopyrine, paraaminobenzoic acid and paraaminosalicylic acid on experimental carditis in mice]. Cas Lek Cesk. 1959 Oct 30;98:1365-9.
40. Wong SC, Ali MA: Hemoglobin E diseases: hematological, analytical, and biosynthetic studies in homozygotes and double heterozygotes for alpha-thalassemia. Am J Hematol. 1982 Aug;13(1):15-21.
41. Costello HD, Caras GJ, Snider DE Jr: Drug resistance among previously treated tuberculosis patients, a brief report. Am Rev Respir Dis. 1980 Feb;121(2):313-6.
42. LEHMANN J: TWENTY YEARS AFTERWARD HISTORICAL NOTES ON THE DISCOVERY OF THE ANTITUBERCULOSIS EFFECT OF PARAAMINOSALICYLIC ACID (PAS) AND THE FIRST CLINICAL TRIALS. Am Rev Respir Dis. 1964 Dec;90:953-6.
43. Vachova-Fribova M, Elis J: [Effect of theophylline and isoprenaline on N-acetylation activity in the rat liver]. Farmakol Toksikol. 1978 Mar-Apr;41(2):191-3.
44. Bader G: [Electron microscopic studies on pathological liver regeneration under the influence of thioacetamide, paraaminosalicylic acid and barbiturate]. Acta Hepatosplenol. 1969 May-Jun;16(3):160-73.