CHEBI:28794 - coumarin

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ChEBI Name coumarin
ChEBI ID CHEBI:28794
Definition A chromenone having the keto group located at the 2-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3906, CHEBI:41552, CHEBI:101256, CHEBI:23402
Supplier Information ChemicalBook:CB1191893, ChemicalBook:CB9854275, eMolecules:477343
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Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the formula NH3. A stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pungent smell. Biologically, it is a common nitrogenous waste, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to fertilisers. Around 70% of ammonia produced industrially is used to make fertilisers in various forms and composition, such as urea and diammonium phosphate. Ammonia in pure form is also applied directly into the soil. Ammonia, either directly or indirectly, is also a building block for the synthesis of many chemicals. Ammonia occurs in nature and has been detected in the interstellar medium. In many countries, it is classified as an extremely hazardous substance. Ammonia is produced biologically in a process called nitrogen fixation, but even more is generated industrially by the Haber process. The process helped revolutionize agriculture by providing cheap fertilizers. The global industrial production of ammonia in 2021 was 235 million tonnes. Industrial ammonia is transported by road in tankers, by rail in tank wagons, by sea in gas carriers, or in cylinders. Ammonia boils at −33.34 °C (−28.012 °F) at a pressure of one atmosphere, but the liquid can often be handled in the laboratory without external cooling. Household ammonia or ammonium hydroxide is a solution of ammonia in water.
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Formula C9H6O2
Net Charge 0
Average Mass 146.145
Monoisotopic Mass 146.03678
InChI InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
InChIKey ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
SMILES O=C1OC2=CC=CC=C2C=C1
Metabolite of Species Details
Eupatorium cannabinum subsp. asiaticum (NCBI:txid102770) Found in aerial part (BTO:0001658). MeOH extract of shade-dried, pulverized aerial parts See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): fluorescent dye

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ChEBI Ontology
Outgoing coumarin (CHEBI:28794) has role fluorescent dye (CHEBI:51121)
coumarin (CHEBI:28794) has role human metabolite (CHEBI:77746)
coumarin (CHEBI:28794) has role plant metabolite (CHEBI:76924)
coumarin (CHEBI:28794) is a coumarins (CHEBI:23403)
Incoming 3,4-dihydrocoumarin (CHEBI:16151) has functional parent coumarin (CHEBI:28794)
3-(4-chlorophenyl)-2H-1-benzopyran-2-one (CHEBI:79706) has functional parent coumarin (CHEBI:28794)
4-ethyl-7-hydroxy-3-(p-methoxyphenyl)coumarin (CHEBI:34403) has functional parent coumarin (CHEBI:28794)
5,6,7-trimethoxycoumarin (CHEBI:28126) has functional parent coumarin (CHEBI:28794)
6,8-difluoro-4-methylumbelliferyl phosphate (CHEBI:133848) has functional parent coumarin (CHEBI:28794)
6,8-difluoro-4-methylumbelliferyl phosphate (2−) (CHEBI:133849) has functional parent coumarin (CHEBI:28794)
7-hydroxy-3-(4-methoxyphenyl)-4-methylcoumarin (CHEBI:79572) has functional parent coumarin (CHEBI:28794)
7-hydroxy-3-(4-methoxyphenyl)-4-propyl-2H-1-benzopyran-2-one (CHEBI:79571) has functional parent coumarin (CHEBI:28794)
7-methoxycoumarin-4-acetic acid (CHEBI:51666) has functional parent coumarin (CHEBI:28794)
daphnoretin (CHEBI:4324) has functional parent coumarin (CHEBI:28794)
licoarylcoumarin (CHEBI:69100) has functional parent coumarin (CHEBI:28794)
7-[(6-hydroxy-2,5,5,8a-tetramethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydro-1-naphthalenyl)methoxy]-2H-chromen-2-one (CHEBI:141536) is a coumarin (CHEBI:28794)
IUPAC Name
2H-chromen-2-one
Synonyms Sources
1,2-Benzopyrone KEGG COMPOUND
2-Propenoic acid, 3-(2-hydroxyphenyl)-, d-lactone KEGG COMPOUND
2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone KEGG COMPOUND
2H-1-Benzopyran-2-one KEGG COMPOUND
2H-benzo[b]pyran-2-one NIST Chemistry WebBook
5,6-Benzo-2-pyrone KEGG COMPOUND
Benzo-a-pyrone KEGG COMPOUND
Benzo-alpha-pyrone KEGG COMPOUND
cis-o-Coumarinic acid lactone KEGG COMPOUND
Coumarine KEGG COMPOUND
Coumarine KEGG COMPOUND
Coumarinic anhydride KEGG COMPOUND
Cumarin KEGG COMPOUND
o-hydroxycinnamic acid δ-lactone NIST Chemistry WebBook
o-Hydroxycinnamic acid lactone KEGG COMPOUND
Rattex KEGG COMPOUND
Tonka bean camphor KEGG COMPOUND
Manual Xrefs Databases
738 DrugCentral
C00002460 KNApSAcK
C05851 KEGG COMPOUND
COU PDBeChem
Coumarin Wikipedia
COUMARIN MetaCyc
D07751 KEGG DRUG
DB04665 DrugBank
HMDB0001218 HMDB
LSM-2519 LINCS
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Registry Numbers Types Sources
165222 Gmelin Registry Number Gmelin
383644 Reaxys Registry Number Reaxys
91-64-5 CAS Registry Number NIST Chemistry WebBook
91-64-5 CAS Registry Number ChemIDplus
Citations Types Sources
16086027 PubMed citation Europe PMC
16822524 PubMed citation Europe PMC
17988284 PubMed citation Europe PMC
19025869 PubMed citation Europe PMC
20206186 PubMed citation Europe PMC
21046436 PubMed citation Europe PMC
21462332 PubMed citation Europe PMC
21798343 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
8735869 PubMed citation Europe PMC
Last Modified
28 May 2021