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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:09 UTC

HMDB ID

HMDB0014378

Secondary Accession Numbers

HMDB14378

Metabolite Identification

Common Name

Aminosalicylic Acid

Description

Aminosalicylic 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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-HYDROXY-4-aminobenzoIC ACID	ChEBI
4-Aminosalicylate	ChEBI
p-Aminosalicylic acid	ChEBI
Para-amino salicylic acid	ChEBI
PAS	ChEBI
Paser	ChEBI
4-Aminosalicylic acid	Kegg
Pamisyl	Kegg
2-HYDROXY-4-aminobenzoate	Generator
p-Aminosalicylate	Generator
Para-amino salicylate	Generator
Aminosalicylate	Generator
4-ASA	HMDB
Amino-pas	HMDB
Aminosalicylate sodium	HMDB
APAS	HMDB
Para-aminosalicylic acid	HMDB
PASK	HMDB
4 Aminosalicylic acid	HMDB
Rezipas	HMDB
p-Aminosalicylic acid monolithium salt	HMDB
p-Aminosalicylic acid, monosodium salt, dihydrate	HMDB
Acid, aminosalicylic	HMDB
Alumino 4 aminosalicylic acid	HMDB
p Aminosalicylic acid monolithium salt	HMDB
p-Aminosalicylic acid monopotassium salt	HMDB
p Aminosalicylic acid	HMDB
p Aminosalicylic acid monopotassium salt	HMDB
p Aminosalicylic acid monosodium salt	HMDB
p-Aminosalicylic acid, aluminum (2:1) salt	HMDB
Para aminosalicylic acid	HMDB
Alumino-4-aminosalicylic acid	HMDB
p-Aminosalicylic acid monosodium salt	HMDB
p-Aminosalicylic acid, calcium (2:1) salt	HMDB
Aminosalicylic acid	ChEBI

Chemical Formula

C₇H₇NO₃

Average Molecular Weight

153.1354

Monoisotopic Molecular Weight

153.042593095

IUPAC Name

4-amino-2-hydroxybenzoic acid

Traditional Name

aminosalicylic acid

CAS Registry Number

65-49-6

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 Key

WUBBRNOQWQTFEX-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminosalicylic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:27565 )
aminobenzoic acid (CHEBI:27565 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0014378)
Membrane (HMDB: HMDB0014378)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.8 g/L	Not Available
LogP	1.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.8 g/L	ALOGPS
logP	0.62	ALOGPS
logP	0.83	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	2.19	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	14.29 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]+	133.264	31661259
DarkChem	[M-H]-	129.63	31661259
DeepCCS	[M+H]+	129.023	30932474
DeepCCS	[M-H]-	125.193	30932474
DeepCCS	[M-2H]-	162.559	30932474
DeepCCS	[M+Na]+	138.034	30932474
AllCCS	[M+H]+	133.3	32859911
AllCCS	[M+H-H2O]+	128.8	32859911
AllCCS	[M+NH4]+	137.5	32859911
AllCCS	[M+Na]+	138.7	32859911
AllCCS	[M-H]-	128.1	32859911
AllCCS	[M+Na-2H]-	129.5	32859911
AllCCS	[M+HCOO]-	131.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aminosalicylic Acid	NC1=CC(O)=C(C=C1)C(O)=O	3248.8	Standard polar	33892256
Aminosalicylic Acid	NC1=CC(O)=C(C=C1)C(O)=O	1844.6	Standard non polar	33892256
Aminosalicylic Acid	NC1=CC(O)=C(C=C1)C(O)=O	1655.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aminosalicylic Acid,1TMS,isomer #1	C[Si](C)(C)OC1=CC(N)=CC=C1C(=O)O	1807.5	Semi standard non polar	33892256
Aminosalicylic Acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O	1781.6	Semi standard non polar	33892256
Aminosalicylic Acid,1TMS,isomer #3	C[Si](C)(C)NC1=CC=C(C(=O)O)C(O)=C1	1943.5	Semi standard non polar	33892256
Aminosalicylic Acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O[Si](C)(C)C	1836.3	Semi standard non polar	33892256
Aminosalicylic Acid,2TMS,isomer #2	C[Si](C)(C)NC1=CC=C(C(=O)O)C(O[Si](C)(C)C)=C1	1965.4	Semi standard non polar	33892256
Aminosalicylic Acid,2TMS,isomer #3	C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O)=C1	1890.3	Semi standard non polar	33892256
Aminosalicylic Acid,2TMS,isomer #4	C[Si](C)(C)N(C1=CC=C(C(=O)O)C(O)=C1)[Si](C)(C)C	1968.4	Semi standard non polar	33892256
Aminosalicylic Acid,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1955.5	Semi standard non polar	33892256
Aminosalicylic Acid,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1979.7	Standard non polar	33892256
Aminosalicylic Acid,3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1975.0	Standard polar	33892256
Aminosalicylic Acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C(=O)O	1950.4	Semi standard non polar	33892256
Aminosalicylic Acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C(=O)O	2087.1	Standard non polar	33892256
Aminosalicylic Acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C(=O)O	1982.3	Standard polar	33892256
Aminosalicylic Acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O	1881.8	Semi standard non polar	33892256
Aminosalicylic Acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O	1976.3	Standard non polar	33892256
Aminosalicylic Acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O	1984.3	Standard polar	33892256
Aminosalicylic Acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	1962.3	Semi standard non polar	33892256
Aminosalicylic Acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	1983.2	Standard non polar	33892256
Aminosalicylic Acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	1876.3	Standard polar	33892256
Aminosalicylic Acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(N)=CC=C1C(=O)O	2064.3	Semi standard non polar	33892256
Aminosalicylic Acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O	2028.7	Semi standard non polar	33892256
Aminosalicylic Acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O)C(O)=C1	2242.5	Semi standard non polar	33892256
Aminosalicylic Acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N)C=C1O[Si](C)(C)C(C)(C)C	2316.6	Semi standard non polar	33892256
Aminosalicylic Acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C1	2518.6	Semi standard non polar	33892256
Aminosalicylic Acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=C1	2409.6	Semi standard non polar	33892256
Aminosalicylic Acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC=C(C(=O)O)C(O)=C1)[Si](C)(C)C(C)(C)C	2468.1	Semi standard non polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #1	CC(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)=C1	2616.4	Semi standard non polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #1	CC(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)=C1	2588.4	Standard non polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #1	CC(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)=C1	2359.5	Standard polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #2	CC(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)O	2636.2	Semi standard non polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #2	CC(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)O	2676.6	Standard non polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #2	CC(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)O	2321.7	Standard polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #3	CC(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	2598.4	Semi standard non polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #3	CC(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	2569.8	Standard non polar	33892256
Aminosalicylic Acid,3TBDMS,isomer #3	CC(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	2328.4	Standard polar	33892256
Aminosalicylic Acid,4TBDMS,isomer #1	CC(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)C	2794.4	Semi standard non polar	33892256
Aminosalicylic Acid,4TBDMS,isomer #1	CC(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)C	2775.0	Standard non polar	33892256
Aminosalicylic Acid,4TBDMS,isomer #1	CC(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)C	2364.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aminosalicylic Acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-2900000000-f96d42a6d732787e860e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminosalicylic Acid GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-2190000000-77c54a0901141e0c25cc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminosalicylic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminosalicylic Acid 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 - Aminosalicylic Acid LC-ESI-qTof , Positive-QTOF	splash10-0002-3962000000-2dfafa7266e72ac813b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0900000000-9edb9b6028f854f76708	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-1900000000-e893f1439cefbeef271a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-5900000000-09273d1390d26a8def2d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOF	splash10-066r-9200000000-e029b385a8c32e95b6b7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid LC-ESI-QQ , negative-QTOF	splash10-00ku-9000000000-58cccd83d40f8fade4dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid , positive-QTOF	splash10-06dr-2900200000-832b5b02326d8b11bac4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Positive-QTOF	splash10-000i-4900000000-8f56b41d56d984600d2e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Positive-QTOF	splash10-0f89-9000000000-de31b7181a8ba3e3c60b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Positive-QTOF	splash10-000i-0900000000-77b21d59e31f1fe41a28	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Positive-QTOF	splash10-0udr-0900000000-a497dd61e37afd19159f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Positive-QTOF	splash10-000i-0900000000-771daa6ebfd132e803a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Positive-QTOF	splash10-00ku-9400000000-a2c0beef5eb5e0f96f27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Negative-QTOF	splash10-0zfr-1900000000-f74138cc6d19303f955c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Negative-QTOF	splash10-0a4i-2900000000-82ef8276edc66459ee1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Negative-QTOF	splash10-0a4l-9500000000-347557516c4726a8670d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Positive-QTOF	splash10-0udr-0900000000-7bc1a9fe6d66a88b37d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Positive-QTOF	splash10-000i-0900000000-ae2965ede5d26e091cdb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Positive-QTOF	splash10-014i-9100000000-5a68b4449891b42a477d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 10V, Negative-QTOF	splash10-0udi-0900000000-ffca2fee4deb986a1b34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 20V, Negative-QTOF	splash10-0pb9-1900000000-ca3768868cf936ca2311	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminosalicylic Acid 40V, Negative-QTOF	splash10-00kf-9000000000-e1a89b3e2a6ece9b67b4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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
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 DB00233	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00233	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00233

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4488

KEGG Compound ID

C02518

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aminosalicylic_Acid

METLIN ID

Not Available

PubChem Compound

4649

PDB ID

BHA

ChEBI ID

27565

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

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 ]
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 ]
Iyawoo K: Tuberculosis in Malaysia: problems and prospect of treatment and control. Tuberculosis (Edinb). 2004;84(1-2):4-7. [PubMed:14670340 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
MILLER FF, GREEN RA: Loeffler's syndrome due to paraaminosalicylic acid. Dis Chest. 1962 Jul;42:100-3. [PubMed:14473996 ]
Miroshnichenko II, Sokolova GB, Mokhireva LV: [Clinical pharmacokinetics of para-aminosalicylic acid tablets]. Antibiot Khimioter. 2009;54(1-2):20-4. [PubMed:19499713 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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

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

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 ]
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

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

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

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

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

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 ]

Showing metabocard for Aminosalicylic Acid (HMDB0014378)

MOL for HMDB0014378 (Aminosalicylic Acid)

3D MOL for HMDB0014378 (Aminosalicylic Acid)

3D SDF for HMDB0014378 (Aminosalicylic Acid)

3D-SDF for HMDB0014378 (Aminosalicylic Acid)

PDB for HMDB0014378 (Aminosalicylic Acid)

3D PDB for HMDB0014378 (Aminosalicylic Acid)

SMILES for HMDB0014378 (Aminosalicylic Acid)

INCHI for HMDB0014378 (Aminosalicylic Acid)

Structure for HMDB0014378 (Aminosalicylic Acid)

3D Structure for HMDB0014378 (Aminosalicylic Acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

References

References

References