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Showing metabocard for Aminosalicylic Acid (HMDB0014378)

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enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:09 UTC
HMDB IDHMDB0014378
Secondary Accession Numbers
  • HMDB14378
Metabolite Identification
Common NameAminosalicylic Acid
DescriptionAminosalicylic Acid is only found in individuals that have used or taken this drug. It is an antitubercular agent often administered in association with isoniazid. The sodium salt of the drug is better tolerated than the free acid. [PubChem]There are two mechanisms responsible for aminosalicylic acid's bacteriostatic action against Mycobacterium tuberculosis. Firstly, aminosalicylic acid inhibits folic acid synthesis (without potentiation with antifolic compounds). The binding of para-aminobenzoic acid to pteridine synthetase acts as the first step in folic acid synthesis. Aminosalicylic acid binds pteridine synthetase with greater affinity than para-aminobenzoic acid, effectively inhibiting the synthesis of folic acid. As bacteria are unable to use external sources of folic acid, cell growth and multiplication slows. Secondly, aminosalicylic acid may inhibit the synthesis of the cell wall component, mycobactin, thus reducing iron uptake by M. tuberculosis.
Structure
Data?1676999889
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014378 (Aminosalicylic Acid)

233
  Mrv0541 02231214322D          

 11 11  0  0  0  0            999 V2000
    2.0930    0.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for HMDB0014378 (Aminosalicylic Acid)

HMDB0014378
     RDKit          3D
Aminosalicylic Acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.0762   -0.2424    0.0300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715   -0.1872    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352   -1.3501    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4414   -1.2531    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0800   -0.0525    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5349    0.0192    0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559    1.1120   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -1.1662    0.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214    1.1094   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9891    2.3480   -0.0875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    1.0567   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5847   -0.3406    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5837   -0.1839   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -2.3323    0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863   -2.2112    0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453   -1.5029   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    3.1932   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6048    1.9841   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  8 16  1  0
 10 17  1  0
 11 18  1  0
M  END
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3D SDF for HMDB0014378 (Aminosalicylic Acid)

233
  Mrv0541 02231214322D          

 11 11  0  0  0  0            999 V2000
    2.0930    0.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014378

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC(O)=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)

> <INCHI_KEY>
WUBBRNOQWQTFEX-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.1354

> <EXACT_MASS>
153.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.29465219368035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-2-hydroxybenzoic acid

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
0.82507511626819

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.223689649295505

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.675350131493757

> <JCHEM_PKA_STRONGEST_BASIC>
2.1883174763812283

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
39.9955

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminosalicylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0014378 (Aminosalicylic Acid)

HMDB0014378
     RDKit          3D
Aminosalicylic Acid
 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.0762   -0.2424    0.0300 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715   -0.1872    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352   -1.3501    0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4414   -1.2531    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0800   -0.0525    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5349    0.0192    0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1559    1.1120   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -1.1662    0.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214    1.1094   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9891    2.3480   -0.0875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0556    1.0567   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5847   -0.3406    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5837   -0.1839   -0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -2.3323    0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863   -2.2112    0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453   -1.5029   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4442    3.1932   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6048    1.9841   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  8 16  1  0
 10 17  1  0
 11 18  1  0
M  END
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PDB for HMDB0014378 (Aminosalicylic Acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 233                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.907   0.916   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.908   3.226   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.241   3.226   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.574  -3.704   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574   0.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.241   0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -2.164   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -1.394   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908   0.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.908  -1.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   2.456   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    7                                                            
CONECT    5    6    9   11                                                  
CONECT    6    1    5    8                                                  
CONECT    7    4    8   10                                                  
CONECT    8    6    7                                                       
CONECT    9    5   10                                                       
CONECT   10    7    9                                                       
CONECT   11    2    3    5                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0014378 (Aminosalicylic Acid)

COMPND    HMDB0014378
HETATM    1  N1  UNL     1      -3.076  -0.242   0.030  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.671  -0.187   0.031  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.935  -1.350   0.089  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.441  -1.253   0.088  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.080  -0.053   0.030  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.535   0.019   0.030  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.156   1.112  -0.022  1.00  0.00           O  
HETATM    8  O2  UNL     1       3.247  -1.166   0.090  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.321   1.109  -0.028  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.989   2.348  -0.088  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.056   1.057  -0.029  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.585  -0.341   0.916  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.584  -0.184  -0.860  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.434  -2.332   0.136  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.986  -2.211   0.136  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.745  -1.503  -0.711  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.444   3.193  -0.130  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.605   1.984  -0.076  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3   11
CONECT    3    4   14
CONECT    4    5    5   15
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   16
CONECT    9   10   11   11
CONECT   10   17
CONECT   11   18
END
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SMILES for HMDB0014378 (Aminosalicylic Acid)

NC1=CC(O)=C(C=C1)C(O)=O
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INCHI for HMDB0014378 (Aminosalicylic Acid)

InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
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 Weight153.1354
Monoisotopic Molecular Weight153.042593095
IUPAC Name4-amino-2-hydroxybenzoic acid
Traditional Nameaminosalicylic acid
CAS Registry Number65-49-6
SMILES
NC1=CC(O)=C(C=C1)C(O)=O
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.8 g/LNot Available
LogP1.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.26431661259
DarkChem[M-H]-129.6331661259
DeepCCS[M+H]+129.02330932474
DeepCCS[M-H]-125.19330932474
DeepCCS[M-2H]-162.55930932474
DeepCCS[M+Na]+138.03430932474
AllCCS[M+H]+133.332859911
AllCCS[M+H-H2O]+128.832859911
AllCCS[M+NH4]+137.532859911
AllCCS[M+Na]+138.732859911
AllCCS[M-H]-128.132859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-131.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.45 minutes32390414
Predicted by Siyang on May 30, 20229.6318 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.59 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid64.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid798.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid314.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid71.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid186.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid62.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid261.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid320.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)116.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid638.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid95.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid817.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid214.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid262.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate572.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA258.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water227.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Aminosalicylic AcidNC1=CC(O)=C(C=C1)C(O)=O3248.8Standard polar33892256
Aminosalicylic AcidNC1=CC(O)=C(C=C1)C(O)=O1844.6Standard non polar33892256
Aminosalicylic AcidNC1=CC(O)=C(C=C1)C(O)=O1655.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aminosalicylic Acid,1TMS,isomer #1C[Si](C)(C)OC1=CC(N)=CC=C1C(=O)O1807.5Semi standard non polar33892256
Aminosalicylic Acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O1781.6Semi standard non polar33892256
Aminosalicylic Acid,1TMS,isomer #3C[Si](C)(C)NC1=CC=C(C(=O)O)C(O)=C11943.5Semi standard non polar33892256
Aminosalicylic Acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O[Si](C)(C)C1836.3Semi standard non polar33892256
Aminosalicylic Acid,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(C(=O)O)C(O[Si](C)(C)C)=C11965.4Semi standard non polar33892256
Aminosalicylic Acid,2TMS,isomer #3C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O)=C11890.3Semi standard non polar33892256
Aminosalicylic Acid,2TMS,isomer #4C[Si](C)(C)N(C1=CC=C(C(=O)O)C(O)=C1)[Si](C)(C)C1968.4Semi standard non polar33892256
Aminosalicylic Acid,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C11955.5Semi standard non polar33892256
Aminosalicylic Acid,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C11979.7Standard non polar33892256
Aminosalicylic Acid,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C11975.0Standard polar33892256
Aminosalicylic Acid,3TMS,isomer #2C[Si](C)(C)OC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C(=O)O1950.4Semi standard non polar33892256
Aminosalicylic Acid,3TMS,isomer #2C[Si](C)(C)OC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C(=O)O2087.1Standard non polar33892256
Aminosalicylic Acid,3TMS,isomer #2C[Si](C)(C)OC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C(=O)O1982.3Standard polar33892256
Aminosalicylic Acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O1881.8Semi standard non polar33892256
Aminosalicylic Acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O1976.3Standard non polar33892256
Aminosalicylic Acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O1984.3Standard polar33892256
Aminosalicylic Acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C1962.3Semi standard non polar33892256
Aminosalicylic Acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C1983.2Standard non polar33892256
Aminosalicylic Acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C1876.3Standard polar33892256
Aminosalicylic Acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(N)=CC=C1C(=O)O2064.3Semi standard non polar33892256
Aminosalicylic Acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O2028.7Semi standard non polar33892256
Aminosalicylic Acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O)C(O)=C12242.5Semi standard non polar33892256
Aminosalicylic Acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O[Si](C)(C)C(C)(C)C2316.6Semi standard non polar33892256
Aminosalicylic Acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C12518.6Semi standard non polar33892256
Aminosalicylic Acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=C12409.6Semi standard non polar33892256
Aminosalicylic Acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C1=CC=C(C(=O)O)C(O)=C1)[Si](C)(C)C(C)(C)C2468.1Semi standard non polar33892256
Aminosalicylic Acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12616.4Semi standard non polar33892256
Aminosalicylic Acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12588.4Standard non polar33892256
Aminosalicylic Acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12359.5Standard polar33892256
Aminosalicylic Acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1C(=O)O2636.2Semi standard non polar33892256
Aminosalicylic Acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1C(=O)O2676.6Standard non polar33892256
Aminosalicylic Acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1C(=O)O2321.7Standard polar33892256
Aminosalicylic Acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2598.4Semi standard non polar33892256
Aminosalicylic Acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2569.8Standard non polar33892256
Aminosalicylic Acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O2328.4Standard polar33892256
Aminosalicylic Acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2794.4Semi standard non polar33892256
Aminosalicylic Acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2775.0Standard non polar33892256
Aminosalicylic Acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2364.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aminosalicylic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-2900000000-f96d42a6d732787e860e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminosalicylic Acid GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-2190000000-77c54a0901141e0c25cc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminosalicylic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aminosalicylic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-qTof , Positive-QTOFsplash10-0002-3962000000-2dfafa7266e72ac813b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0900000000-9edb9b6028f854f767082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-1900000000-e893f1439cefbeef271a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOFsplash10-0a4i-5900000000-09273d1390d26a8def2d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOFsplash10-066r-9200000000-e029b385a8c32e95b6b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOFsplash10-00ku-9000000000-58cccd83d40f8fade4dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid , positive-QTOFsplash10-06dr-2900200000-832b5b02326d8b11bac42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid 20V, Positive-QTOFsplash10-000i-4900000000-8f56b41d56d984600d2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid 40V, Positive-QTOFsplash10-0f89-9000000000-de31b7181a8ba3e3c60b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aminosalicylic Acid 10V, Positive-QTOFsplash10-000i-0900000000-77b21d59e31f1fe41a282021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Positive-QTOFsplash10-0udr-0900000000-a497dd61e37afd19159f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Positive-QTOFsplash10-000i-0900000000-771daa6ebfd132e803a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Positive-QTOFsplash10-00ku-9400000000-a2c0beef5eb5e0f96f272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Negative-QTOFsplash10-0zfr-1900000000-f74138cc6d19303f955c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Negative-QTOFsplash10-0a4i-2900000000-82ef8276edc66459ee1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Negative-QTOFsplash10-0a4l-9500000000-347557516c4726a8670d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Positive-QTOFsplash10-0udr-0900000000-7bc1a9fe6d66a88b37d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Positive-QTOFsplash10-000i-0900000000-ae2965ede5d26e091cdb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Positive-QTOFsplash10-014i-9100000000-5a68b4449891b42a477d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Negative-QTOFsplash10-0udi-0900000000-ffca2fee4deb986a1b342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Negative-QTOFsplash10-0pb9-1900000000-ca3768868cf936ca23112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Negative-QTOFsplash10-00kf-9000000000-e1a89b3e2a6ece9b67b42021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00233 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00233 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00233
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4488
KEGG Compound IDC02518
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminosalicylic_Acid
METLIN IDNot Available
PubChem Compound4649
PDB IDBHA
ChEBI ID27565
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:13684569 ]
  2. JUHASZ P, GALAMBOS G: [A simple paper-indicator method for the demonstration of paraaminosalicylic acid (PAS) in urine]. Tuberkulozis. 1961 Jun;14:186-7. [PubMed:13790963 ]
  3. Iyawoo K: Tuberculosis in Malaysia: problems and prospect of treatment and control. Tuberculosis (Edinb). 2004;84(1-2):4-7. [PubMed:14670340 ]
  4. Authors unspecified: Controlled trial of short-course regimens of chemotherapy in the ambulatory treatment of spinal tuberculosis. Results at three years of a study in Korea. Twelfth report of the Medical Research Council Working Party on Tuberculosis of the Spine. J Bone Joint Surg Br. 1993 Mar;75(2):240-8. [PubMed:8444944 ]
  5. Tiitinen H, Mattila MJ: Modification of the serum isoniazid levels by different preparations of paraaminosalicylic acid. Arzneimittelforschung. 1968 May;18(5):623-5. [PubMed:5755895 ]
  6. 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. [PubMed:5560983 ]
  7. 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. [PubMed:15494824 ]
  8. 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. [PubMed:14478036 ]
  9. 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. [PubMed:14408481 ]
  10. 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. [PubMed:7428368 ]
  11. 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. [PubMed:14423031 ]
  12. MILLER FF, GREEN RA: Loeffler's syndrome due to paraaminosalicylic acid. Dis Chest. 1962 Jul;42:100-3. [PubMed:14473996 ]
  13. Miroshnichenko II, Sokolova GB, Mokhireva LV: [Clinical pharmacokinetics of para-aminosalicylic acid tablets]. Antibiot Khimioter. 2009;54(1-2):20-4. [PubMed:19499713 ]
  14. 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. [PubMed:14443158 ]
  15. 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. [PubMed:7137163 ]
  16. 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. [PubMed:6767427 ]
  17. 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. [PubMed:14233801 ]
  18. 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. [PubMed:658363 ]
  19. 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. [PubMed:5799611 ]

Enzymes

Enzyme Details
1. Group IIE secretory phospholipase A2
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Enzyme Details
2. Myeloperoxidase
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. von Ritter C, Grisham MB, Granger DN: Sulfasalazine metabolites and dapsone attenuate formyl-methionyl-leucyl-phenylalanine-induced mucosal injury in rat ileum. Gastroenterology. 1989 Mar;96(3):811-6. [PubMed:2563347 ]
  2. Gorgulu S, Yagci G, Kaymakcioglu N, Ozkara M, Kurt B, Ozcan A, Kaya O, Sadir S, Tufan T: Hyperbaric oxygen enhances the efficiency of 5-aminosalicylic acid in acetic acid-induced colitis in rats. Dig Dis Sci. 2006 Mar;51(3):480-7. [PubMed:16614956 ]
Enzyme Details
3. Arachidonate 5-lipoxygenase
General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
References
  1. Nielsen OH, Bukhave K, Elmgreen J, Ahnfelt-Ronne I: Inhibition of 5-lipoxygenase pathway of arachidonic acid metabolism in human neutrophils by sulfasalazine and 5-aminosalicylic acid. Dig Dis Sci. 1987 Jun;32(6):577-82. [PubMed:2882965 ]
  2. Allgayer H, Eisenburg J, Paumgartner G: Soybean lipoxygenase inhibition: studies with the sulphasalazine metabolites N-acetylaminosalicylic acid, 5-aminosalicylic acid and sulphapyridine. Eur J Clin Pharmacol. 1984;26(4):449-51. [PubMed:6428914 ]
  3. Sircar JC, Schwender CF, Carethers ME: Inhibition of soybean lipoxygenase by sulfasalazine and 5-aminosalicylic acid: a possible mode of action in ulcerative colitis. Biochem Pharmacol. 1983 Jan 1;32(1):170-2. [PubMed:6131674 ]
Enzyme Details
4. Prostaglandin G/H synthase 2
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Mifflin RC, Saada JI, Di Mari JF, Valentich JD, Adegboyega PA, Powell DW: Aspirin-mediated COX-2 transcript stabilization via sustained p38 activation in human intestinal myofibroblasts. Mol Pharmacol. 2004 Feb;65(2):470-8. [PubMed:14742690 ]
  2. Generini S, Fiori G, Matucci Cerinic M: Therapy of spondylarthropathy in inflammatory bowel disease. Clin Exp Rheumatol. 2002 Nov-Dec;20(6 Suppl 28):S88-94. [PubMed:12463455 ]
  3. Distrutti E, Sediari L, Mencarelli A, Renga B, Orlandi S, Russo G, Caliendo G, Santagada V, Cirino G, Wallace JL, Fiorucci S: 5-Amino-2-hydroxybenzoic acid 4-(5-thioxo-5H-[1,2]dithiol-3yl)-phenyl ester (ATB-429), a hydrogen sulfide-releasing derivative of mesalamine, exerts antinociceptive effects in a model of postinflammatory hypersensitivity. J Pharmacol Exp Ther. 2006 Oct;319(1):447-58. Epub 2006 Jul 19. [PubMed:16855178 ]
  4. Cipolla G, Crema F, Sacco S, Moro E, de Ponti F, Frigo G: Nonsteroidal anti-inflammatory drugs and inflammatory bowel disease: current perspectives. Pharmacol Res. 2002 Jul;46(1):1-6. [PubMed:12208114 ]
  5. Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS: Inhibition of extracellular release of proinflammatory secretory phospholipase A2 (sPLA2) by sulfasalazine: a novel mechanism of anti-inflammatory activity. Biochem Pharmacol. 1997 Jun 15;53(12):1901-7. [PubMed:9256165 ]
Enzyme Details
5. Inhibitor of nuclear factor kappa-B kinase subunit alpha
General function:
Involved in protein kinase activity
Specific function:
Acts as part of the IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF- kappa-B complex and ultimately the degradation of the inhibitor. As part of the non-canonical pathway of NF-kappa-B activation, the MAP3K14-activated CHUK/IKKA homodimer phosphorylates NFKB2/p100 associated with RelB, inducing its proteolytic processing to NFKB2/p52 and the formation of NF-kappa-B RelB-p52 complexes. Also phosphorylates NCOA3. Phosphorylates 'Ser-10' of histone H3 at NF- kappa-B-regulated promoters during inflammatory responses triggered by cytokines
Gene Name:
CHUK
Uniprot ID:
O15111
Molecular weight:
84652.9
References
  1. Bantel H, Berg C, Vieth M, Stolte M, Kruis W, Schulze-Osthoff K: Mesalazine inhibits activation of transcription factor NF-kappaB in inflamed mucosa of patients with ulcerative colitis. Am J Gastroenterol. 2000 Dec;95(12):3452-7. [PubMed:11151876 ]
  2. Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [PubMed:12950415 ]
  3. Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [PubMed:11054378 ]