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CHEBI:17846 - (S)-naringenin
| Formula | C15H12O5 |
| Net Charge | 0 |
| Average Mass | 272.256 |
| Monoisotopic Mass | 272.06847 |
| SMILES | O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)cc(O)c21 |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| 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 |
|---|---|
| (−)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one | IUBMB |
| (−)-(2S)-naringenin | IUBMB |
| (-)-(2S)-Naringenin | KEGG COMPOUND |
| (2S)-Naringenin | KEGG COMPOUND |
| 4',5,7-trihydroxyflavanone | ChEBI |
| 4',5,7-Trihydroxyflavanone | KEGG COMPOUND |
| UniProt Name | Source |
|---|---|
| (2S)-naringenin | UniProt |
| Manual Xrefs | Databases |
|---|---|
| C00000982 | KNApSAcK |
| C00509 | KEGG COMPOUND |
| DB03467 | DrugBank |
| HMDB0002670 | HMDB |
| LMPK12140001 | LIPID MAPS |
| NAR | PDBeChem |
| Naringenin | Wikipedia |
| NARINGENIN-CMPD | MetaCyc |
| Registry Numbers | Sources |
|---|---|
| Reaxys:90699 | Reaxys |
| CAS:480-41-1 | KEGG COMPOUND |
| CAS:480-41-1 | ChemIDplus |
| Citations |
|---|