4-aminosalicylic acid (CHEBI:27565)

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CHEBI:27565 - 4-aminosalicylic acid

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ChEBI Name	4-aminosalicylic acid

ChEBI ID	CHEBI:27565

Definition	An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41152, CHEBI:1789, CHEBI:20320

Supplier Information	ChemicalBook:CB9679687, eMolecules:477205, ZINC000000000922

Download	Molfile XML SDF

more structures >>

Molfile

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18 18 0 0 0 0 999 V2000

0.8194 2.6603 -0.5620 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0002 3.4714 -0.9445 O 0 0 0 0 0 0 0 0 0 0 0 0

2.1272 2.9849 -0.5366 O 0 0 0 0 0 0 0 0 0 0 0 0

0.3845 1.3249 -0.1261 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9771 0.9842 -0.1521 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3766 -0.2725 0.2656 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4289 -1.1930 0.6966 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9224 -0.8505 0.7188 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3258 0.3886 0.3142 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8970 1.8848 -0.5786 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8306 -2.4579 1.1105 N 0 0 0 0 0 0 0 0 0 0 0 0

2.4137 3.8621 -0.8233 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4226 -0.5413 0.2492 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6524 -1.5695 1.0584 H 0 0 0 0 0 0 0 0 0 0 0 0

2.3746 0.6459 0.3349 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1813 2.3836 0.1984 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1700 -3.1006 1.4139 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7685 -2.6995 1.0908 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

3 12 1 0 0 0 0

4 5 4 0 0 0 0

4 9 4 0 0 0 0

5 6 4 0 0 0 0

5 10 1 0 0 0 0

6 7 4 0 0 0 0

6 13 1 0 0 0 0

7 8 4 0 0 0 0

7 11 1 0 0 0 0

8 9 4 0 0 0 0

8 14 1 0 0 0 0

9 15 1 0 0 0 0

10 16 1 0 0 0 0

11 17 1 0 0 0 0

11 18 1 0 0 0 0

M END): 15 ms

reading 18 atoms

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Wikipedia	License
Aspirin () is the genericized trademark for acetylsalicylic acid (ASA), a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and inflammation, and as an antithrombotic. Specific inflammatory conditions that aspirin is used to treat include Kawasaki disease, pericarditis, and rheumatic fever. Aspirin is also used long-term to help prevent further heart attacks, ischaemic strokes, and blood clots in people at high risk. For pain or fever, effects typically begin within 30 minutes. Aspirin works similarly to other NSAIDs but also suppresses the normal functioning of platelets. One common adverse effect is an upset stomach. More significant side effects include stomach ulcers, stomach bleeding, and worsening asthma. Bleeding risk is greater among those who are older, drink alcohol, take other NSAIDs, or are on other blood thinners. Aspirin is not recommended in the last part of pregnancy. It is not generally recommended in children with infections because of the risk of Reye syndrome. High doses may result in ringing in the ears. A precursor to aspirin found in the bark of the willow tree (genus Salix) has been used for its health effects for at least 2,400 years. In 1853, chemist Charles Frédéric Gerhardt treated the medicine sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first time. Over the next 50 years, other chemists, mostly of the German company Bayer, established the chemical structure and devised more efficient production methods.: 69–75 Felix Hoffmann (or Arthur Eichengrün) of Bayer was the first to produce acetylsalicylic acid in a pure, stable form in 1897. By 1899, Bayer had dubbed this drug Aspirin and was selling it globally.: 27 Aspirin is available without medical prescription as a proprietary or generic medication in most jurisdictions. It is one of the most widely used medications globally, with an estimated 40,000 tonnes (44,000 tons) (50 to 120 billion pills) consumed each year, and is on the World Health Organization's List of Essential Medicines. In 2022, it was the 36th most commonly prescribed medication in the United States, with more than 16 million prescriptions.
Read full article at Wikipedia

Formula

C7H7NO3

Net Charge

Average Mass

153.13540

Monoisotopic Mass

153.04259

InChI

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

InChIKey

WUBBRNOQWQTFEX-UHFFFAOYSA-N

SMILES

Nc1ccc(C(O)=O)c(O)c1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.

Application(s):	antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	4-aminosalicylic acid (CHEBI:27565) has functional parent salicylic acid (CHEBI:16914) 4-aminosalicylic acid (CHEBI:27565) has role antitubercular agent (CHEBI:33231) 4-aminosalicylic acid (CHEBI:27565) is a aminobenzoic acid (CHEBI:22495) 4-aminosalicylic acid (CHEBI:27565) is a phenols (CHEBI:33853) 4-aminosalicylic acid (CHEBI:27565) is conjugate acid of 4-aminosalicylate(1−) (CHEBI:137598)

Incoming	4-aminosalicylate(1−) (CHEBI:137598) is conjugate base of 4-aminosalicylic acid (CHEBI:27565)

IUPAC Name

4-amino-2-hydroxybenzoic acid

Synonyms	Sources
2-HYDROXY-4-AMINOBENZOIC ACID	PDBeChem
4-Aminosalicylate	KEGG COMPOUND
4-Aminosalicylic acid	KEGG COMPOUND
Aminosalicylic acid	ChemIDplus
p-aminosalicylic acid	NIST Chemistry WebBook
Para-amino salicylic acid	ChemIDplus
PAS	ChemIDplus

Brand Name	Source
Paser	DrugBank

Manual Xrefs	Databases
2050	DrugCentral
Aminosalicylic_Acid	Wikipedia
BHA	PDBeChem
C02518	KEGG COMPOUND
D00162	KEGG DRUG
DB00233	DrugBank
DE50835	Patent
HMDB0014378	HMDB
LSM-5862	LINCS
US2844625	Patent
US427564	Patent
View more database links

Registry Numbers	Types	Sources
306153	Gmelin Registry Number	Gmelin
473071	Reaxys Registry Number	Reaxys
65-49-6	CAS Registry Number	ChemIDplus
65-49-6	CAS Registry Number	NIST Chemistry WebBook

Citations	Types	Sources
11621575	PubMed citation	Europe PMC
1650428	PubMed citation	Europe PMC
23118010	PubMed citation	Europe PMC
24663015	PubMed citation	Europe PMC
25050392	PubMed citation	Europe PMC
25421465	PubMed citation	Europe PMC
25605031	PubMed citation	Europe PMC
25963985	PubMed citation	Europe PMC
26004847	PubMed citation	Europe PMC
26033719	PubMed citation	Europe PMC
26277036	PubMed citation	Europe PMC
26596566	PubMed citation	Europe PMC
26848874	PubMed citation	Europe PMC
27021327	PubMed citation	Europe PMC
27491492	PubMed citation	Europe PMC
27617928	PubMed citation	Europe PMC
27671064	PubMed citation	Europe PMC
28011126	PubMed citation	Europe PMC
28223391	PubMed citation	Europe PMC
28394286	PubMed citation	Europe PMC
28408267	PubMed citation	Europe PMC
28567674	PubMed citation	Europe PMC
28651968	PubMed citation	Europe PMC
28717039	PubMed citation	Europe PMC
28812999	PubMed citation	Europe PMC

Last Modified

17 August 2017

General Comment
2014-05-06	It is found in samples of blood and urine of individuals who have used this drug.

CHEBI:27565 - 4-aminosalicylic acid

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