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CHEBI:17846 - (S)-naringenin

ChEBI IDCHEBI:17846
ChEBI Name(S)-naringenin
Stars
ASCII Name(S)-naringenin
DefinitionThe (S)-enantiomer of naringenin.
Secondary ChEBI IDsCHEBI:7483, CHEBI:14640, CHEBI:25484, CHEBI:25488, CHEBI:44288
Last Modified19 August 2020
DownloadsMolfile
FormulaC15H12O5
Net Charge0
Average Mass272.256
Monoisotopic Mass272.06847
SMILESO=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)cc(O)c21
InChIInChI=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
InChIKeyFTVWIRXFELQLPI-ZDUSSCGKSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Pittocaulon velatum (IPNI:238587-1)
root (BTO:0001188) PubMed (21661732) Methanol extract of dried and ground stems and roots
stem (BTO:0001300) PubMed (21661732) Methanol extract of dried and ground stems and roots
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
(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 Relation(s)
(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-prenylnaringenin (CHEBI:27566) has functional parent (S)-naringenin (CHEBI:17846)
6,8-diprenylnaringenin (CHEBI:2156) 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  Source
NaringeninKEGG COMPOUND
4',5,7-TrihydroxyflavanoneKEGG COMPOUND
4',5,7-trihydroxyflavanoneChEBI
(S)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneIUBMB
NARINGENINPDBeChem
(−)-(2S)-naringeninIUBMB
UniProt Name  Source
(2S)-naringeninUniProt
Manual XrefsDatabases
C00509KEGG COMPOUND
NARPDBeChem
LMPK12140001LIPID MAPS
DB03467DrugBank
NARINGENIN-CMPDMetaCyc
NaringeninWikipedia
HMDB0002670HMDB
C00000982KNApSAcK
Registry NumbersSources
Reaxys:90699Reaxys
CAS:480-41-1KEGG COMPOUND
CAS:480-41-1ChemIDplus
Citations