salicylic acid (CHEBI:16914)

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CHEBI:16914 - salicylic acid

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ChEBI Name	salicylic acid

ChEBI ID	CHEBI:16914

Definition	A monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves.

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

Secondary ChEBI IDs	CHEBI:45521, CHEBI:9006, CHEBI:26597

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

Molfile

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16 16 0 0 0 0 999 V2000

-0.2657 -2.1792 -0.2069 C 0 0 0 0 0 0 0 0 0 4 0 0

0.8778 -1.4464 -0.5633 C 0 0 0 0 0 0 0 0 0 3 0 0

-1.3851 -1.5156 0.3195 C 0 0 0 0 0 0 0 0 0 5 0 0

-0.2130 0.6482 0.1414 C 0 0 0 0 0 0 0 0 0 1 0 0

0.9085 -0.0462 -0.3915 C 0 0 0 0 0 0 0 0 0 2 0 0

-1.3564 -0.1180 0.4859 C 0 0 0 0 0 0 0 0 0 6 0 0

-1.2386 2.6967 0.3147 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2130 2.0295 0.3335 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8202 2.6595 0.5399 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9612 0.5509 -0.7437 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2830 -3.1944 -0.3309 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6844 -1.9438 -0.9499 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2164 -2.0501 0.5822 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1933 0.3231 0.8781 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8126 3.5305 0.6698 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6481 0.1138 -1.0786 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 4 0 0 0 0

1 3 4 0 0 0 0

4 8 1 0 0 0 0

4 5 4 0 0 0 0

2 5 4 0 0 0 0

5 10 1 0 0 0 0

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8 7 2 0 0 0 0

8 9 1 0 0 0 0

1 11 1 0 0 0 0

2 12 1 0 0 0 0

3 13 1 0 0 0 0

6 14 1 0 0 0 0

9 15 1 0 0 0 0

10 16 1 0 0 0 0

M END): 18 ms

reading 16 atoms

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Wikipedia	License
Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless (or white), bitter-tasting solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.
Read full article at Wikipedia

Formula

C7H6O3

Net Charge

Average Mass

138.12070

Monoisotopic Mass

138.03169

InChI

InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)

InChIKey

YGSDEFSMJLZEOE-UHFFFAOYSA-N

SMILES

OC(=O)c1ccccc1O

Metabolite of Species	Details
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Cordyceps sinensis (NCBI:txid72228)	Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed

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

Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor An EC 1.11.1.* (peroxidases) inhibitor that inhibits the action of L-ascorbate peroxidase (EC 1.11.1.11). antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. plant hormone A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.

Application(s):	antiinfective agent A substance used in the prophylaxis or therapy of infectious diseases. keratolytic drug A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	salicylic acid (CHEBI:16914) has role algal metabolite (CHEBI:84735) salicylic acid (CHEBI:16914) has role antifungal agent (CHEBI:35718) salicylic acid (CHEBI:16914) has role antiinfective agent (CHEBI:35441) salicylic acid (CHEBI:16914) has role EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor (CHEBI:73181) salicylic acid (CHEBI:16914) has role keratolytic drug (CHEBI:50176) salicylic acid (CHEBI:16914) has role plant hormone (CHEBI:37848) salicylic acid (CHEBI:16914) has role plant metabolite (CHEBI:76924) salicylic acid (CHEBI:16914) is a monohydroxybenzoic acid (CHEBI:25389) salicylic acid (CHEBI:16914) is conjugate acid of salicylate (CHEBI:30762)

Incoming	1-salicylate glucuronide (CHEBI:73961) has functional parent salicylic acid (CHEBI:16914) 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl]benzoic acid (CHEBI:213766) has functional parent salicylic acid (CHEBI:16914) 2-(D-glucosyloxy)benzoic acid (CHEBI:87766) has functional parent salicylic acid (CHEBI:16914) 2-[[2-[(2-hydroxyphenyl)-oxomethoxy]-1-oxoethyl]amino]-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid methyl ester (CHEBI:121777) has functional parent salicylic acid (CHEBI:16914) 2-hydroxy-3-methylbenzoic acid (3-cyano-4-imino-2-oxopentyl) ester (CHEBI:112747) has functional parent salicylic acid (CHEBI:16914) 2-hydroxy-4-methylbenzoic acid [2-(2-chloroanilino)-2-oxoethyl] ester (CHEBI:116485) has functional parent salicylic acid (CHEBI:16914) 2-Hydroxy-4-trifluoromethyl benzoic acid (CHEBI:174020) has functional parent salicylic acid (CHEBI:16914) 2-hydroxy-5-[(4-methoxyphenyl)sulfamoyl]benzoic acid [2-[1-(3-bicyclo[2.2.1]heptanyl)ethylamino]-2-oxoethyl] ester (CHEBI:121984) has functional parent salicylic acid (CHEBI:16914) 2-hydroxy-6-(12-oxoheptadecyl)benzoic acid (CHEBI:211672) has functional parent salicylic acid (CHEBI:16914) 2-hydroxy-6-(12-oxopentadecyl)benzoic acid (CHEBI:211679) has functional parent salicylic acid (CHEBI:16914) 2-Hydroxy-6-(8,11,14-pentadecatrienyl)benzoic acid (CHEBI:174627) has functional parent salicylic acid (CHEBI:16914) 2-Hydroxy-6-(8-tridecenyl)benzoic acid (CHEBI:192876) has functional parent salicylic acid (CHEBI:16914) 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trien-1-yl]benzoic acid (CHEBI:183726) has functional parent salicylic acid (CHEBI:16914) 2-Hydroxy-6-pentadeca-8,11,14-trienyl benzoic acid (CHEBI:181219) has functional parent salicylic acid (CHEBI:16914) 2-Hydroxy-6-tridecylbenzoic acid (CHEBI:175101) has functional parent salicylic acid (CHEBI:16914) 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester (CHEBI:91642) has functional parent salicylic acid (CHEBI:16914) 2-hydroxybenzoic acid [2-(2-ethoxyanilino)-2-oxo-1-phenylethyl] ester (CHEBI:114677) has functional parent salicylic acid (CHEBI:16914) 2-hydroxybenzoic acid [2-[[(1-methyl-2-pyrrolyl)-oxomethyl]amino]-2-oxoethyl] ester (CHEBI:108199) has functional parent salicylic acid (CHEBI:16914) 2-hydroxybenzoyl-AMP (CHEBI:86457) has functional parent salicylic acid (CHEBI:16914) 2-hydroxybenzoyl-CoA (CHEBI:32587) has functional parent salicylic acid (CHEBI:16914) 2-hydroxyethyl salicylate (CHEBI:86541) has functional parent salicylic acid (CHEBI:16914) 3,5-dinitrosalicylic acid (CHEBI:53648) has functional parent salicylic acid (CHEBI:16914) 3,6-dimethylsalicylic acid (CHEBI:70733) has functional parent salicylic acid (CHEBI:16914) 3-allyl-2-hydroxybenzoic acid (CHEBI:167783) has functional parent salicylic acid (CHEBI:16914) 3-formylsalicylic acid (CHEBI:34334) has functional parent salicylic acid (CHEBI:16914) 3-Hydroxyphthalic acid (CHEBI:204117) has functional parent salicylic acid (CHEBI:16914) 3-methylsalicylic acid (CHEBI:20141) has functional parent salicylic acid (CHEBI:16914) 4-[amino(carboxy)methyl]-2-hydroxybenzoic acid (CHEBI:93904) has functional parent salicylic acid (CHEBI:16914) 4-acetamidosalicylic acid (CHEBI:63816) has functional parent salicylic acid (CHEBI:16914) 4-aminosalicylic acid (CHEBI:27565) has functional parent salicylic acid (CHEBI:16914) 4-formylsalicylic acid (CHEBI:20367) has functional parent salicylic acid (CHEBI:16914) 4-hydroxymethylsalicylic acid (CHEBI:20415) has functional parent salicylic acid (CHEBI:16914) 4-methylsalicylic acid (CHEBI:20450) has functional parent salicylic acid (CHEBI:16914) 4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate) (CHEBI:174940) has functional parent salicylic acid (CHEBI:16914) 5-(diethylsulfamoyl)-2-hydroxybenzoic acid [2-oxo-2-[4-(trifluoromethoxy)anilino]ethyl] ester (CHEBI:123403) has functional parent salicylic acid (CHEBI:16914) 5-[amino(carboxy)methyl]-2-hydroxybenzoic acid (CHEBI:93840) has functional parent salicylic acid (CHEBI:16914) 5-formylsalicylic acid (CHEBI:137371) has functional parent salicylic acid (CHEBI:16914) 5-nitrososalicylic acid (CHEBI:143303) has functional parent salicylic acid (CHEBI:16914) 6-((8Z,11Z,14Z)-heptadeca-8,11,14-trien-1-yl)salicylic acid (CHEBI:186627) has functional parent salicylic acid (CHEBI:16914) 6-((Z)-pentadec-10-en-1-yl)salicylic acid (CHEBI:186923) has functional parent salicylic acid (CHEBI:16914) 6-((Z)-pentadec-8-en-1-yl)salicylic acid (CHEBI:193466) has functional parent salicylic acid (CHEBI:16914) 6-formylsalicylic acid (CHEBI:208549) has functional parent salicylic acid (CHEBI:16914) 6-hydroxy platensimycin A1 methyl ester (CHEBI:68270) has functional parent salicylic acid (CHEBI:16914) 6-methylsalicylic acid (CHEBI:17637) has functional parent salicylic acid (CHEBI:16914) O-(S-2-hydroxybenzoylpantetheine-4'-phosphoryl)-L-serine residue (CHEBI:86462) has functional parent salicylic acid (CHEBI:16914) D-glucosyl salicylate (CHEBI:133564) has functional parent salicylic acid (CHEBI:16914) acetylsalicylic acid (CHEBI:15365) has functional parent salicylic acid (CHEBI:16914) Ampelomin G (CHEBI:223031) has functional parent salicylic acid (CHEBI:16914) anacardic acid (CHEBI:2696) has functional parent salicylic acid (CHEBI:16914) Antibiotic SB 202742 (CHEBI:174937) has functional parent salicylic acid (CHEBI:16914) Benzyl salicylate (CHEBI:165211) has functional parent salicylic acid (CHEBI:16914) Butyl salicylate (CHEBI:173949) has functional parent salicylic acid (CHEBI:16914) Chloropupukeananin (CHEBI:216291) has functional parent salicylic acid (CHEBI:16914) Chloropupukeanone A (CHEBI:207995) has functional parent salicylic acid (CHEBI:16914) Choline salicylate (CHEBI:3668) has functional parent salicylic acid (CHEBI:16914) diflunisal (CHEBI:39669) has functional parent salicylic acid (CHEBI:16914) Ethyl 4-ethoxy-2-hydroxy-3,6-dimethylbenzoate (CHEBI:214582) has functional parent salicylic acid (CHEBI:16914) Ethylhexyl salicylate (CHEBI:88639) has functional parent salicylic acid (CHEBI:16914) Gentisic acid sodium (CHEBI:189437) has functional parent salicylic acid (CHEBI:16914) Gibbestatin B (CHEBI:220560) has functional parent salicylic acid (CHEBI:16914) Ginkgoic acid (CHEBI:5354) has functional parent salicylic acid (CHEBI:16914) Ginkgolic Acid C17-1 (CHEBI:228873) has functional parent salicylic acid (CHEBI:16914) Glycerol 1-hydroxy-2,5-dimethyl benzoate (CHEBI:227951) has functional parent salicylic acid (CHEBI:16914) hydroxytetracaine (CHEBI:135162) has functional parent salicylic acid (CHEBI:16914) Isoamyl salicylate (CHEBI:173601) has functional parent salicylic acid (CHEBI:16914) Isobutyl salicylate (CHEBI:173947) has functional parent salicylic acid (CHEBI:16914) isopropyl salicylate (CHEBI:38703) has functional parent salicylic acid (CHEBI:16914) menthyl salicylate (CHEBI:135976) has functional parent salicylic acid (CHEBI:16914) mesalamine (CHEBI:6775) has functional parent salicylic acid (CHEBI:16914) Methyl 2,6-dihydroxybenzoate (CHEBI:192874) has functional parent salicylic acid (CHEBI:16914) Methyl 2-(10-heptadecenyl)-6-hydroxybenzoate (CHEBI:169431) has functional parent salicylic acid (CHEBI:16914) Methyl 4-(4,6-dihydroxy-5-methoxy-2,5-dimethyl-3-oxocyclohexen-1-yl)oxy-2-hydroxy-3,6-dimethylbenzoate (CHEBI:181274) has functional parent salicylic acid (CHEBI:16914) Methyl 5-chloro-2-hydroxybenzoate (CHEBI:194865) has functional parent salicylic acid (CHEBI:16914) methyl salicylate (CHEBI:31832) has functional parent salicylic acid (CHEBI:16914) Nabscebetain A (CHEBI:206787) has functional parent salicylic acid (CHEBI:16914) Nabscebetain B (CHEBI:206794) has functional parent salicylic acid (CHEBI:16914) olsalazine (CHEBI:7770) has functional parent salicylic acid (CHEBI:16914) Phenethyl salicylate (CHEBI:173744) has functional parent salicylic acid (CHEBI:16914) phenyl salicylate (CHEBI:34918) has functional parent salicylic acid (CHEBI:16914) Phomone A (CHEBI:205846) has functional parent salicylic acid (CHEBI:16914) Pleoniol C (CHEBI:214724) has functional parent salicylic acid (CHEBI:16914) promysalin (CHEBI:171658) has functional parent salicylic acid (CHEBI:16914) Roccellatol (CHEBI:220613) has functional parent salicylic acid (CHEBI:16914) Salaceyin A (CHEBI:224587) has functional parent salicylic acid (CHEBI:16914) Salaceyin B (CHEBI:220151) has functional parent salicylic acid (CHEBI:16914) salicylamides (CHEBI:53443) has functional parent salicylic acid (CHEBI:16914) salicylic acid-d4 (CHEBI:178057) has functional parent salicylic acid (CHEBI:16914) salsalate (CHEBI:9014) has functional parent salicylic acid (CHEBI:16914) valerylsalicylic acid (CHEBI:78250) has functional parent salicylic acid (CHEBI:16914) salicylate (CHEBI:30762) is conjugate base of salicylic acid (CHEBI:16914) 2-hydroxybenzoyl group (CHEBI:60335) is substituent group from salicylic acid (CHEBI:16914)

IUPAC Name

2-hydroxybenzoic acid

Synonyms	Sources
2-carboxyphenol	NIST Chemistry WebBook
2-HYDROXYBENZOIC ACID	PDBeChem
o-carboxyphenol	NIST Chemistry WebBook
o-Hydroxybenzoic acid	KEGG COMPOUND
o-hydroxybenzoic acid	NIST Chemistry WebBook
Salicylic acid	KEGG COMPOUND

Manual Xrefs	Databases
2416	DrugCentral
C00000206	KNApSAcK
C00805	KEGG COMPOUND
CPD-110	MetaCyc
D00097	KEGG DRUG
DB00936	DrugBank
HMDB0001895	HMDB
LSM-4763	LINCS
SAL	PDBeChem
Salicylic_Acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
3418	Gmelin Registry Number	Gmelin
69-72-7	CAS Registry Number	KEGG COMPOUND
69-72-7	CAS Registry Number	NIST Chemistry WebBook
69-72-7	CAS Registry Number	ChemIDplus
774890	Reaxys Registry Number	Reaxys

Citations	Types	Sources
11016405	PubMed citation	Europe PMC
12865403	PubMed citation	Europe PMC
1650428	PubMed citation	Europe PMC
19400653	PubMed citation	Europe PMC
19816125	PubMed citation	Europe PMC
22770225	PubMed citation	Europe PMC
29079364	PubMed citation	Europe PMC
32807953	PubMed citation	Europe PMC
3425858	PubMed citation	Europe PMC

Last Modified

25 November 2020

CHEBI:16914 - salicylic acid

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