Compound
(2S)-naringenin
The (S)-enantiomer of naringenin.
Definition from ChEBI (CHEBI:17846), read 2026-09-23. CC BY 4.0.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C15H12O5
- Mass
- 272.256 g/mol
- Charge
- 0
- InChIKey
- FTVWIRXFELQLPI-ZDUSSCGKSA-N
- SMILES
- O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O)cc(O)c21
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
1 entity
1 entities reached.
0 reported hops1 assembled from the scaffold
What the reference databases state
Chemical structure
- (2S)-naringenin 7-O-beta-D-glucoside has the functional parent (2S)-naringeninCompoundChEBI CHEBI:28327Inferred only
Statements
1 statement
1 statement · 1 reference database · Subject: (2S)-naringenin · Sources: Rhea
- (2S)-naringenin is a substrate of LCTProteinRhea RHEA:69671Inferred only
Reactions
12 reactions
(2S)-naringenin+CHEBI:57623CHEBI:50207+diphosphate(3-)
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:15433CC BY 4.0Reference data
(2S)-naringenin+S-adenosyl-L-methionineCHEBI:28927+S-adenosyl-L-homocysteine+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:31539CC BY 4.0Reference data
(2S)-naringenin+2-oxoglutarate(2-)+dioxygenapigenin+succinate(2-)+carbon dioxide+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:32755CC BY 4.0Reference data
(2S)-naringenin+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:31080+oxidized [NADPH--hemoprotein reductase]+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:35487CC BY 4.0Reference data
(2S)-naringenin+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:141994+oxidized [NADPH--hemoprotein reductase]+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:57588CC BY 4.0Reference data
(2S)-naringenin+2-oxoglutarate(2-)+dioxygenCHEBI:15401+succinate(2-)+carbon dioxide
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:61084CC BY 4.0Reference data
(2S)-naringenin+reduced [NADPH--hemoprotein reductase]+dioxygen(S)-eriodictyol+oxidized [NADPH--hemoprotein reductase]+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:61096CC BY 4.0Reference data
(2S)-naringenin+2reduced [NADPH--hemoprotein reductase]+2dioxygenCHEBI:48026+2oxidized [NADPH--hemoprotein reductase]+2water+2hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:61104CC BY 4.0Reference data
(2S)-naringenin+UDP-alpha-D-glucose(2S)-naringenin 7-O-beta-D-glucoside+UDP+hydron
Catalysed by UGT3A2
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:65152CC BY 4.0Reference data
(2S)-naringenin 7-O-beta-D-glucoside+water(2S)-naringenin+beta-D-glucose
Catalysed by LCT
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:69671CC BY 4.0Reference data
(2S)-naringenin+S-adenosyl-L-methionineCHEBI:27552+S-adenosyl-L-homocysteine+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:73287CC BY 4.0Reference data
CHEBI:15413(2S)-naringenin
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:79891CC BY 4.0Reference data
On the label
Labelled products
6 products
Source: NIH DSLD · Ingredient: (2S)-naringenin · 6 products · Declared amount per serving: 36–300 mg (5 products)
6 labels state an amount0 do not
- BioGenesis NutraceuticalsAdrenal Support Plus36 mgper 2 Capsule(s)DSLD:20760
- Centurion LabzOut of Rage XXX50 mgper 11.7 Gram(s)DSLD:201411
- Designs for HealthThermo-EFx300 mgper 1 Capsule(s)DSLD:23265
- i-Prevail SupplementsA.M.P.'D UP200 mgper 1 Capsule(s)DSLD:228497
- Redcon1Total War Pineapple JuiceNaringin Note: 98%0.17 Gram(s)per 6.45 Gram(s)DSLD:237008
- SuperSmartNatural Anti Aromatase SupportGrapefruit extract · standardized to 99% naringin200 mgper 2 Tablet(s)DSLD:332400
Label record: NIH Office of Dietary Supplements · CC0
Other names
11 names
Resolves to: (2S)-naringenin
- Also called
- (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one(-)-(2S)-Naringenin(−)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one(−)-(2S)-naringenin(S)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one4',5,7-trihydroxyflavanoneNARINGENINnaringetolpelargidanonsalipurpol
- Systematic name
- (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one