CHEBI:17846 - (S)-naringenin

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ChEBI Name (S)-naringenin
ChEBI ID CHEBI:17846
ChEBI ASCII Name (S)-naringenin
Definition The (S)-enantiomer of naringenin.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44288, CHEBI:7483, CHEBI:14640, CHEBI:25484, CHEBI:25488
Supplier Information eMolecules:1016027, Selleckchem:Naringenin, ZINC000000156701
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Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit. The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024. High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability. Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs. Similar to furanocoumarins present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications.
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Formula C15H12O5
Net Charge 0
Average Mass 272.25280
Monoisotopic Mass 272.06847
InChI InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
InChIKey FTVWIRXFELQLPI-ZDUSSCGKSA-N
SMILES Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O)cc(O)cc2O1
Metabolite of Species Details
Pittocaulon velatum (IPNI:238587-1) Found in root (BTO:0001188). Methanol extract of dried and ground stems and roots See: PubMed
Pittocaulon velatum (IPNI:238587-1) Found in stem (BTO:0001300). Methanol extract of dried and ground stems and roots See: PubMed
Roles Classification
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.
Application(s): expectorant
Compounds that are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing. Compare with mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration, and antitussives, which suppress the cough reflex.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-naringenin (CHEBI:17846) has role expectorant (CHEBI:77035)
(S)-naringenin (CHEBI:17846) has role plant metabolite (CHEBI:76924)
(S)-naringenin (CHEBI:17846) is a (2S)-flavan-4-one (CHEBI:140377)
(S)-naringenin (CHEBI:17846) is a naringenin (CHEBI:50202)
(S)-naringenin (CHEBI:17846) is conjugate acid of (S)-naringenin(1−) (CHEBI:58292)
(S)-naringenin (CHEBI:17846) is enantiomer of (R)-naringenin (CHEBI:50201)
Incoming (2S)-2-hydroxynaringenin (CHEBI:141994) has functional parent (S)-naringenin (CHEBI:17846)
(2S)-5-hydroxy-4',7-dimethoxyflavanone (CHEBI:192816) has functional parent (S)-naringenin (CHEBI:17846)
4'-methoxy-5,7-dihydroxyflavanone (CHEBI:27552) has functional parent (S)-naringenin (CHEBI:17846)
6,8-diprenylnaringenin (CHEBI:2156) has functional parent (S)-naringenin (CHEBI:17846)
6-prenylnaringenin (CHEBI:27566) has functional parent (S)-naringenin (CHEBI:17846)
8-C-α-L-arabinopyranosyl-7-O-β-D-glucopyranosylnaringenin (CHEBI:70200) has functional parent (S)-naringenin (CHEBI:17846)
carthamidin (CHEBI:80809) has functional parent (S)-naringenin (CHEBI:17846)
isohemiphloin (CHEBI:80529) has functional parent (S)-naringenin (CHEBI:17846)
leachianone G (CHEBI:50208) has functional parent (S)-naringenin (CHEBI:17846)
leufolin A (CHEBI:66575) has functional parent (S)-naringenin (CHEBI:17846)
naringenin 7-O-β-D-glucoside (CHEBI:28327) has functional parent (S)-naringenin (CHEBI:17846)
naringin (CHEBI:28819) has functional parent (S)-naringenin (CHEBI:17846)
narirutin (CHEBI:28705) has functional parent (S)-naringenin (CHEBI:17846)
sakuranetin (CHEBI:28927) has functional parent (S)-naringenin (CHEBI:17846)
selinone (CHEBI:66460) has functional parent (S)-naringenin (CHEBI:17846)
sophoraflavanone A (CHEBI:70023) has functional parent (S)-naringenin (CHEBI:17846)
sophoraflavanone B (CHEBI:50207) has functional parent (S)-naringenin (CHEBI:17846)
sophoraflavanone G (CHEBI:50209) has functional parent (S)-naringenin (CHEBI:17846)
(S)-naringenin(1−) (CHEBI:58292) is conjugate base of (S)-naringenin (CHEBI:17846)
(R)-naringenin (CHEBI:50201) is enantiomer of (S)-naringenin (CHEBI:17846)
IUPAC Name
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
Synonyms Sources
(−)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one IUBMB
(−)-(2S)-naringenin IUBMB
(-)-(2S)-Naringenin KEGG COMPOUND
(2S)-Naringenin KEGG COMPOUND
(2S)-naringenin UniProt
(S)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one IUBMB
4',5,7-trihydroxyflavanone ChEBI
4',5,7-Trihydroxyflavanone KEGG COMPOUND
Naringenin KEGG COMPOUND
NARINGENIN PDBeChem
naringetol HMDB
pelargidanon HMDB
salipurpol HMDB
Manual Xrefs Databases
C00000982 KNApSAcK
C00509 KEGG COMPOUND
DB03467 DrugBank
HMDB0002670 HMDB
LMPK12140001 LIPID MAPS
NAR PDBeChem
Naringenin Wikipedia
NARINGENIN-CMPD MetaCyc
View more database links
Registry Numbers Types Sources
480-41-1 CAS Registry Number ChemIDplus
90699 Reaxys Registry Number Reaxys
Citations
Lin BQ, Li PB, Wang YG, Peng W, Wu Z, Su WW, Ji H (2008)
The expectorant activity of naringenin.
Pulmonary pharmacology & therapeutics 21, 259-263 [PubMed:17664077]
[show Abstract]
Felgines C, Texier O, Morand C, Manach C, Scalbert A, Régerat F, Rémésy C (2000)
Bioavailability of the flavanone naringenin and its glycosides in rats.
American journal of physiology. Gastrointestinal and liver physiology 279, G1148-54 [PubMed:11093936]
[show Abstract]
Last Modified
19 August 2020