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Showing metabocard for Mesalazine (HMDB0014389)

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enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:09 UTC
HMDB IDHMDB0014389
Secondary Accession Numbers
  • HMDB14389
Metabolite Identification
Common NameMesalazine
DescriptionMesalazine is only found in individuals that have used or taken this drug. It is an anti-inflammatory agent, structurally related to the salicylates, which is active in inflammatory bowel disease. It is considered to be the active moiety of sulphasalazine. (From Martindale, The Extra Pharmacopoeia, 30th ed)Although the mechanism of action of mesalazine is not fully understood, it appears to be topical rather than systemic. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes and hydroxyeicosatetraenoic acids, is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalazine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin production in the colon.
Structure
Data?1676999889
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014389 (Mesalazine)

244
  Mrv0541 02231214322D          

 11 11  0  0  0  0            999 V2000
    2.0930    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for HMDB0014389 (Mesalazine)

HMDB0014389
     RDKit          3D
Mesalazine
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.5515    0.9674    1.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    0.2710    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565   -1.0773    0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895   -1.7369   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096   -1.1129   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.7991   -1.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8054    0.2187   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0407    0.9263   -0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028    0.3186   -0.8969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    2.2654   -0.0570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583    0.9003    0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907    1.0998    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3308    1.2955    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.5611    0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617   -2.7889   -0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389   -2.7638   -1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0616    2.6176    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    1.9593    0.6967 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
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
 10 17  1  0
 11 18  1  0
M  END
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3D SDF for HMDB0014389 (Mesalazine)

244
  Mrv0541 02231214322D          

 11 11  0  0  0  0            999 V2000
    2.0930    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014389

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
KBOPZPXVLCULAV-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.1354

> <EXACT_MASS>
153.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.263819873124916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
-0.28978240563320434

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.475226170274773

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.024188346479524

> <JCHEM_PKA_STRONGEST_BASIC>
5.871587939823654

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
39.9955

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mesalazine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0014389 (Mesalazine)

HMDB0014389
     RDKit          3D
Mesalazine
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.5515    0.9674    1.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    0.2710    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565   -1.0773    0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895   -1.7369   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096   -1.1129   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -1.7991   -1.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8054    0.2187   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0407    0.9263   -0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028    0.3186   -0.8969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    2.2654   -0.0570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583    0.9003    0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907    1.0998    2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3308    1.2955    0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.5611    0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617   -2.7889   -0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7389   -2.7638   -1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0616    2.6176    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    1.9593    0.6967 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
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
 10 17  1  0
 11 18  1  0
M  END
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PDB for HMDB0014389 (Mesalazine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 244                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.907   0.385   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.908   2.695   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.241   2.695   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.242  -2.695   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.908  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.908  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   1.925   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    6                                                            
CONECT    5    7    8   11                                                  
CONECT    6    4    7    9                                                  
CONECT    7    5    6                                                       
CONECT    8    1    5   10                                                  
CONECT    9    6   10                                                       
CONECT   10    8    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 HMDB0014389 (Mesalazine)

COMPND    HMDB0014389
HETATM    1  N1  UNL     1       2.551   0.967   1.300  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.449   0.271   0.706  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.556  -1.077   0.373  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.490  -1.737  -0.197  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.710  -1.113  -0.460  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.788  -1.799  -1.042  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.805   0.219  -0.127  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.041   0.926  -0.379  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.003   0.319  -0.897  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.173   2.265  -0.057  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.258   0.900   0.448  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.491   1.100   2.333  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.331   1.296   0.695  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.497  -1.561   0.580  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.562  -2.789  -0.462  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.739  -2.764  -1.291  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.062   2.618   0.310  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.136   1.959   0.697  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    7
CONECT    6   16
CONECT    7    8   11   11
CONECT    8    9    9   10
CONECT   10   17
CONECT   11   18
END
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SMILES for HMDB0014389 (Mesalazine)

NC1=CC(C(O)=O)=C(O)C=C1
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INCHI for HMDB0014389 (Mesalazine)

InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
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 Weight153.1354
Monoisotopic Molecular Weight153.042593095
IUPAC Name5-amino-2-hydroxybenzoic acid
Traditional Namemesalazine
CAS Registry Number89-57-6
SMILES
NC1=CC(C(O)=O)=C(O)C=C1
InChI Identifier
InChI=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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point283 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.2 g/LNot Available
LogP1.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available134.722http://allccs.zhulab.cn/database/detail?ID=AllCCS00000880
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.35631661259
DarkChem[M-H]-129.57631661259
DeepCCS[M+H]+131.64530932474
DeepCCS[M-H]-128.33230932474
DeepCCS[M-2H]-165.58430932474
DeepCCS[M+Na]+141.11730932474
AllCCS[M+H]+133.132859911
AllCCS[M+H-H2O]+128.632859911
AllCCS[M+NH4]+137.332859911
AllCCS[M+Na]+138.532859911
AllCCS[M-H]-126.832859911
AllCCS[M+Na-2H]-128.232859911
AllCCS[M+HCOO]-129.732859911

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, 2022.1.84 minutes32390414
Predicted by Siyang on May 30, 20229.6162 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.76 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid69.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid825.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid312.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid69.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid184.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid56.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid259.9 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 Acid302.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)118.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid637.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid98.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid823.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid210.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid258.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate570.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA280.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water236.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MesalazineNC1=CC(C(O)=O)=C(O)C=C13287.2Standard polar33892256
MesalazineNC1=CC(C(O)=O)=C(O)C=C11813.5Standard non polar33892256
MesalazineNC1=CC(C(O)=O)=C(O)C=C11620.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mesalazine,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O1750.5Semi standard non polar33892256
Mesalazine,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(N)C=C1C(=O)O1778.7Semi standard non polar33892256
Mesalazine,1TMS,isomer #3C[Si](C)(C)NC1=CC=C(O)C(C(=O)O)=C11898.1Semi standard non polar33892256
Mesalazine,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O[Si](C)(C)C1811.5Semi standard non polar33892256
Mesalazine,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(O)C(C(=O)O[Si](C)(C)C)=C11848.9Semi standard non polar33892256
Mesalazine,2TMS,isomer #3C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O)=C11925.1Semi standard non polar33892256
Mesalazine,2TMS,isomer #4C[Si](C)(C)N(C1=CC=C(O)C(C(=O)O)=C1)[Si](C)(C)C1946.5Semi standard non polar33892256
Mesalazine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C11939.7Semi standard non polar33892256
Mesalazine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C11951.3Standard non polar33892256
Mesalazine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C11966.6Standard polar33892256
Mesalazine,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O1860.0Semi standard non polar33892256
Mesalazine,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O1954.0Standard non polar33892256
Mesalazine,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O1977.7Standard polar33892256
Mesalazine,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O1945.6Semi standard non polar33892256
Mesalazine,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O2076.1Standard non polar33892256
Mesalazine,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O1977.7Standard polar33892256
Mesalazine,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C1975.9Semi standard non polar33892256
Mesalazine,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C1977.7Standard non polar33892256
Mesalazine,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C1870.5Standard polar33892256
Mesalazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O1998.3Semi standard non polar33892256
Mesalazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(N)C=C1C(=O)O2030.7Semi standard non polar33892256
Mesalazine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=C(O)C(C(=O)O)=C12198.1Semi standard non polar33892256
Mesalazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O[Si](C)(C)C(C)(C)C2288.8Semi standard non polar33892256
Mesalazine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C12335.0Semi standard non polar33892256
Mesalazine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C12472.1Semi standard non polar33892256
Mesalazine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C(C(=O)O)=C1)[Si](C)(C)C(C)(C)C2421.6Semi standard non polar33892256
Mesalazine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C12601.7Semi standard non polar33892256
Mesalazine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C12572.2Standard non polar33892256
Mesalazine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C12352.2Standard polar33892256
Mesalazine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2547.6Semi standard non polar33892256
Mesalazine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2550.1Standard non polar33892256
Mesalazine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2324.3Standard polar33892256
Mesalazine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O2636.7Semi standard non polar33892256
Mesalazine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O2667.7Standard non polar33892256
Mesalazine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1C(=O)O2321.5Standard polar33892256
Mesalazine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2793.9Semi standard non polar33892256
Mesalazine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2757.6Standard non polar33892256
Mesalazine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2358.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mesalazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zg0-1900000000-8c59ef73371ab7058ab92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesalazine GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-6290000000-8c65a0e3aa600dc402bb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesalazine 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 - Mesalazine LC-ESI-QFT , positive-QTOFsplash10-0f79-0900000000-db75ae2d436dd6156c912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesalazine 10V, Positive-QTOFsplash10-000i-0900000000-31f47e60332bc9d52dc52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesalazine 35V, Positive-QTOFsplash10-0a59-4900000000-e694f0e584d434cd6c192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesalazine 20V, Positive-QTOFsplash10-0a5i-5900000000-5e487b4d3f15751bc4212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesalazine 40V, Positive-QTOFsplash10-0il0-9000000000-65d9d31a1ef1458009982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesalazine 35V, Negative-QTOFsplash10-0a4i-0900000000-afe56677019b761236ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mesalazine 35V, Positive-QTOFsplash10-0f79-0900000000-e6285983e501467965c12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 10V, Positive-QTOFsplash10-0udi-0900000000-f9d037b61fba1f9bc0032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 20V, Positive-QTOFsplash10-0pbi-0900000000-8692528b7d752229a1742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 40V, Positive-QTOFsplash10-057i-9300000000-b6f08e642ac27344075c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 10V, Negative-QTOFsplash10-0zfr-0900000000-ff6f4a59111a558719162016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 20V, Negative-QTOFsplash10-0a4i-0900000000-b2691ada23e4712099ee2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 40V, Negative-QTOFsplash10-0a4i-7900000000-cb7f7dfff58bf74b852a2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 10V, Negative-QTOFsplash10-0udi-0900000000-4d1e5c8d16c81a250fcc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 20V, Negative-QTOFsplash10-0a4i-0900000000-875d8abd6f6773a406342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 40V, Negative-QTOFsplash10-0a6r-9700000000-b6a77be3dfe8ecfbaf8e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 10V, Positive-QTOFsplash10-000i-0900000000-e04ca92dcfe7d48570112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 20V, Positive-QTOFsplash10-052r-1900000000-34d228a18521111a48cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesalazine 40V, Positive-QTOFsplash10-001i-9200000000-b4371439ac0a5b3d574a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)2022-02-11FELIX 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+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
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00244 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00244 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  2. Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
Associated OMIM IDsNone
DrugBank IDDB00244
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3933
KEGG Compound IDNot Available
BioCyc IDCPD-12711
BiGG IDNot Available
Wikipedia LinkMesalamine
METLIN IDNot Available
PubChem Compound4075
PDB IDNot Available
ChEBI ID6775
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. Wikipedia [Link]

Enzymes

Enzyme Details
1. 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. Nandi J, Saud B, Zinkievich JM, Palma DT, Levine RA: 5-aminosalicylic acid improves indomethacin-induced enteropathy by inhibiting iNOS transcription in rats. Dig Dis Sci. 2008 Jan;53(1):123-32. Epub 2007 May 15. [PubMed:17503181 ]
Enzyme Details
2. 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
3. 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
4. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. 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 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Enzyme Details
5. Inhibitor of nuclear factor kappa-B kinase subunit beta
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. Also phosphorylates NCOA3
Gene Name:
IKBKB
Uniprot ID:
O14920
Molecular weight:
86563.2
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 ]
Enzyme Details
6. 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 ]
Enzyme Details
7. Peroxisome proliferator-activated receptor gamma
General function:
Involved in DNA binding
Specific function:
Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular weight:
57619.6
References
  1. Rousseaux C, Lefebvre B, Dubuquoy L, Lefebvre P, Romano O, Auwerx J, Metzger D, Wahli W, Desvergne B, Naccari GC, Chavatte P, Farce A, Bulois P, Cortot A, Colombel JF, Desreumaux P: Intestinal antiinflammatory effect of 5-aminosalicylic acid is dependent on peroxisome proliferator-activated receptor-gamma. J Exp Med. 2005 Apr 18;201(8):1205-15. Epub 2005 Apr 11. [PubMed:15824083 ]
  2. Schwab M, Reynders V, Loitsch S, Shastri YM, Steinhilber D, Schroder O, Stein J: PPARgamma is involved in mesalazine-mediated induction of apoptosis and inhibition of cell growth in colon cancer cells. Carcinogenesis. 2008 Jul;29(7):1407-14. doi: 10.1093/carcin/bgn118. Epub 2008 Jun 9. [PubMed:18544567 ]
  3. Linard C, Gremy O, Benderitter M: Reduction of peroxisome proliferation-activated receptor gamma expression by gamma-irradiation as a mechanism contributing to inflammatory response in rat colon: modulation by the 5-aminosalicylic acid agonist. J Pharmacol Exp Ther. 2008 Mar;324(3):911-20. Epub 2007 Dec 12. [PubMed:18077625 ]
  4. Desreumaux P, Ghosh S: Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. Aliment Pharmacol Ther. 2006 Sep;24 Suppl 1:2-9. [PubMed:16939423 ]