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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:09 UTC

HMDB ID

HMDB0014389

Secondary Accession Numbers

HMDB14389

Metabolite Identification

Common Name

Mesalazine

Description

Mesalazine 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Carboxy-4-hydroxyaniline	ChEBI
5-Aminosalicylic acid	ChEBI
5-ASA	ChEBI
Asacol	ChEBI
Asacolitin	ChEBI
Canasa	ChEBI
Claversal	ChEBI
Fisalamine	ChEBI
Iialda	ChEBI
Lixacol	ChEBI
m-Aminosalicylic acid	ChEBI
Mesalazina	ChEBI
Mesalazinum	ChEBI
Mesasal	ChEBI
p-Aminosalicylsaeure	ChEBI
Pentasa	ChEBI
Rowasa	ChEBI
Salofalk	ChEBI
Apriso	Kegg
Delzicol	Kegg
Lialda	Kegg
Sfrowasa	Kegg
5-Aminosalicylate	Generator
m-Aminosalicylate	Generator
Mesalamine	HMDB
5 Aminosalicylic acid	HMDB
Antigen brand OF mesalamine	HMDB
Henning berlin brand OF mesalamine	HMDB
Hydrochloride, mesalamine	HMDB
Norgine brand OF mesalamine	HMDB
Procter and gamble brand OF mesalamine	HMDB
Sanofi synthelabo brand OF mesalamine	HMDB
m Aminosalicylic acid	HMDB
Meta aminosalicylic acid	HMDB
Byk brand OF mesalamine	HMDB
GlaxoSmithKline brand OF mesalamine	HMDB
Mesalamine hydrochloride	HMDB
Monosodium salt, mesalamine	HMDB
Novo 5 asa	HMDB
Provalis brand OF mesalamine	HMDB
Schering plough brand OF mesalamine	HMDB
Yamanouchi brand OF mesalamine	HMDB
5 Aminosalicylate	HMDB
Asacolon	HMDB
Ascolitin	HMDB
Axcan brand OF mesalamine	HMDB
Celltech brand OF mesalamine	HMDB
Falk brand OF mesalamine	HMDB
Ferring brand OF mesalamine	HMDB
Merckle brand OF mesalamine	HMDB
Novo5 asa	HMDB
Novopharm brand OF mesalamine	HMDB
Allphar brand OF mesalamine	HMDB
Farmasa brand OF mesalamine	HMDB
Fivasa	HMDB
Mesalamine monosodium salt	HMDB
Novo-5 asa	HMDB
Schering-plough brand OF mesalamine	HMDB
SmithKline brand OF mesalamine	HMDB
Solvay brand OF mesalamine	HMDB
Meta-aminosalicylic acid	HMDB
Mesalazine	ChEBI

Chemical Formula

C₇H₇NO₃

Average Molecular Weight

153.1354

Monoisotopic Molecular Weight

153.042593095

IUPAC Name

5-amino-2-hydroxybenzoic acid

Traditional Name

mesalazine

CAS Registry Number

89-57-6

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 Key

KBOPZPXVLCULAV-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:6775 )
phenols (CHEBI:6775 )
aromatic amine (CHEBI:6775 )
amino acid (CHEBI:6775 )
monohydroxybenzoic acid (CHEBI:6775 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0014389)
Membrane (HMDB: HMDB0014389)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)
Feces (PMID: 21761941)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	283 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	12.2 g/L	Not Available
LogP	1.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	134.722	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000880

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.2 g/L	ALOGPS
logP	0.75	ALOGPS
logP	-0.29	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.02	ChemAxon
pKa (Strongest Basic)	5.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40 m³·mol⁻¹	ChemAxon
Polarizability	14.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.356	31661259
DarkChem	[M-H]-	129.576	31661259
DeepCCS	[M+H]+	131.645	30932474
DeepCCS	[M-H]-	128.332	30932474
DeepCCS	[M-2H]-	165.584	30932474
DeepCCS	[M+Na]+	141.117	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.5	32859911
AllCCS	[M-H]-	126.8	32859911
AllCCS	[M+Na-2H]-	128.2	32859911
AllCCS	[M+HCOO]-	129.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mesalazine	NC1=CC(C(O)=O)=C(O)C=C1	3287.2	Standard polar	33892256
Mesalazine	NC1=CC(C(O)=O)=C(O)C=C1	1813.5	Standard non polar	33892256
Mesalazine	NC1=CC(C(O)=O)=C(O)C=C1	1620.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mesalazine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O	1750.5	Semi standard non polar	33892256
Mesalazine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(N)C=C1C(=O)O	1778.7	Semi standard non polar	33892256
Mesalazine,1TMS,isomer #3	C[Si](C)(C)NC1=CC=C(O)C(C(=O)O)=C1	1898.1	Semi standard non polar	33892256
Mesalazine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O[Si](C)(C)C	1811.5	Semi standard non polar	33892256
Mesalazine,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(O)C(C(=O)O[Si](C)(C)C)=C1	1848.9	Semi standard non polar	33892256
Mesalazine,2TMS,isomer #3	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O)=C1	1925.1	Semi standard non polar	33892256
Mesalazine,2TMS,isomer #4	C[Si](C)(C)N(C1=CC=C(O)C(C(=O)O)=C1)[Si](C)(C)C	1946.5	Semi standard non polar	33892256
Mesalazine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	1939.7	Semi standard non polar	33892256
Mesalazine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	1951.3	Standard non polar	33892256
Mesalazine,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C1	1966.6	Standard polar	33892256
Mesalazine,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	1860.0	Semi standard non polar	33892256
Mesalazine,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	1954.0	Standard non polar	33892256
Mesalazine,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	1977.7	Standard polar	33892256
Mesalazine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O	1945.6	Semi standard non polar	33892256
Mesalazine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O	2076.1	Standard non polar	33892256
Mesalazine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1C(=O)O	1977.7	Standard polar	33892256
Mesalazine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1975.9	Semi standard non polar	33892256
Mesalazine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1977.7	Standard non polar	33892256
Mesalazine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1870.5	Standard polar	33892256
Mesalazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O	1998.3	Semi standard non polar	33892256
Mesalazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(N)C=C1C(=O)O	2030.7	Semi standard non polar	33892256
Mesalazine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=C(O)C(C(=O)O)=C1	2198.1	Semi standard non polar	33892256
Mesalazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N)=CC=C1O[Si](C)(C)C(C)(C)C	2288.8	Semi standard non polar	33892256
Mesalazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2335.0	Semi standard non polar	33892256
Mesalazine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C1	2472.1	Semi standard non polar	33892256
Mesalazine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C(C(=O)O)=C1)[Si](C)(C)C(C)(C)C	2421.6	Semi standard non polar	33892256
Mesalazine,3TBDMS,isomer #1	CC(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)=C1	2601.7	Semi standard non polar	33892256
Mesalazine,3TBDMS,isomer #1	CC(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)=C1	2572.2	Standard non polar	33892256
Mesalazine,3TBDMS,isomer #1	CC(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)=C1	2352.2	Standard polar	33892256
Mesalazine,3TBDMS,isomer #2	CC(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	2547.6	Semi standard non polar	33892256
Mesalazine,3TBDMS,isomer #2	CC(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	2550.1	Standard non polar	33892256
Mesalazine,3TBDMS,isomer #2	CC(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	2324.3	Standard polar	33892256
Mesalazine,3TBDMS,isomer #3	CC(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)O	2636.7	Semi standard non polar	33892256
Mesalazine,3TBDMS,isomer #3	CC(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)O	2667.7	Standard non polar	33892256
Mesalazine,3TBDMS,isomer #3	CC(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)O	2321.5	Standard polar	33892256
Mesalazine,4TBDMS,isomer #1	CC(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)C	2793.9	Semi standard non polar	33892256
Mesalazine,4TBDMS,isomer #1	CC(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)C	2757.6	Standard non polar	33892256
Mesalazine,4TBDMS,isomer #1	CC(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)C	2358.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mesalazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg0-1900000000-8c59ef73371ab7058ab9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesalazine GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-6290000000-8c65a0e3aa600dc402bb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesalazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesalazine 35V, Negative-QTOF	splash10-0a4i-0900000000-afe56677019b761236ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesalazine LC-ESI-QFT , positive-QTOF	splash10-0f79-0900000000-db75ae2d436dd6156c91	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesalazine 10V, Positive-QTOF	splash10-000i-0900000000-31f47e60332bc9d52dc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesalazine 35V, Positive-QTOF	splash10-0a59-4900000000-e694f0e584d434cd6c19	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesalazine 20V, Positive-QTOF	splash10-0a5i-5900000000-5e487b4d3f15751bc421	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesalazine 40V, Positive-QTOF	splash10-0il0-9000000000-65d9d31a1ef145800998	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mesalazine 35V, Positive-QTOF	splash10-0f79-0900000000-e6285983e501467965c1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 10V, Negative-QTOF	splash10-0zfr-0900000000-ff6f4a59111a55871916	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 20V, Negative-QTOF	splash10-0a4i-0900000000-b2691ada23e4712099ee	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 40V, Negative-QTOF	splash10-0a4i-7900000000-cb7f7dfff58bf74b852a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 10V, Negative-QTOF	splash10-0udi-0900000000-4d1e5c8d16c81a250fcc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 20V, Negative-QTOF	splash10-0a4i-0900000000-875d8abd6f6773a40634	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 40V, Negative-QTOF	splash10-0a6r-9700000000-b6a77be3dfe8ecfbaf8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 10V, Positive-QTOF	splash10-0udi-0900000000-f9d037b61fba1f9bc003	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 20V, Positive-QTOF	splash10-0pbi-0900000000-8692528b7d752229a174	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 40V, Positive-QTOF	splash10-057i-9300000000-b6f08e642ac27344075c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 10V, Positive-QTOF	splash10-000i-0900000000-e04ca92dcfe7d4857011	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 20V, Positive-QTOF	splash10-052r-1900000000-34d228a18521111a48cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesalazine 40V, Positive-QTOF	splash10-001i-9200000000-b4371439ac0a5b3d574a	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00244	21059682	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21761941	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00244	21059682	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	17269711	details

Associated Disorders and Diseases

Disease References

Irritable bowel syndrome
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
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 ] 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 IDs

None

External Links

DrugBank ID

DB00244

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3933

KEGG Compound ID

Not Available

BioCyc ID

CPD-12711

BiGG ID

Not Available

Wikipedia Link

Mesalamine

METLIN ID

Not Available

PubChem Compound

4075

PDB ID

Not Available

ChEBI ID

6775

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

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

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 ]
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 ]
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

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 ]
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 ]
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 ]
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 ]
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

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 ]
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

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 ]
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 ]
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

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 ]
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 ]
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

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 ]
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 ]
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 ]
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 ]

Showing metabocard for Mesalazine (HMDB0014389)

MOL for HMDB0014389 (Mesalazine)

3D MOL for HMDB0014389 (Mesalazine)

3D SDF for HMDB0014389 (Mesalazine)

3D-SDF for HMDB0014389 (Mesalazine)

PDB for HMDB0014389 (Mesalazine)

3D PDB for HMDB0014389 (Mesalazine)

SMILES for HMDB0014389 (Mesalazine)

INCHI for HMDB0014389 (Mesalazine)

Structure for HMDB0014389 (Mesalazine)

3D Structure for HMDB0014389 (Mesalazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

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