CHEBI:17846 - (S)-naringenin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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
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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 Waiting for Citations Types Sources
11093936 PubMed citation Europe PMC
17664077 PubMed citation Europe PMC
Last Modified
19 August 2020