General Information of MET (ID: META00834)
Name Naringenin
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(-)-(2S)-Naringenin; (-)-Naringenin; (2S)-Naringenin; (S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one', 4',5,7-Trihydroxyflavanone, 'Naringetol; Asahina; Naringenine; Pelargidanon; Salipurol; Salipurpol
Source Food;Drug;Polyketides;Food;Drug;TCM Ingredients;Naringin;Plant Metabolite; Herbal Ingredients In-Vivo Metabolism
Structure Type   Flavans  (Click to Show/Hide the Complete Structure Type Hierarchy)
Phenylpropanoids and polyketides
Flavonoids
Flavans
PubChem CID
439246
HMDB ID
HMDB0002670
Formula
C15H12O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00509
DrugBank ID
DB03467
ChEBI ID
17846
FooDB ID
FDB000678
ChemSpider ID
388383
METLIN ID
3401
Physicochemical Properties Molecular Weight 272.25 Topological Polar Surface Area 87
XlogP 2.4 Complexity 363
Heavy Atom Count 20 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
Naringenin (not to be confused with naringin) is a flavanone that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater. This substance has also been shown to repair DNA. Scientists exposed cells to 80 micomoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24 percent in that very short period of time. Unfortunately, this bioflavonoid is difficult to absorb on oral ingestion. Only 15% of ingested naringenin will get absorbed, in the human gastrointestinal tract, in the best case scenario. A full glass of orange juice will supply about enough naringenin to achieve a concentration of about 0.5 micromoles per liter. But, one has to wonder, if given more time than 24 hours, would lower concentrations have similar effects. Wikipedia. Naringenin is a biomarker for the consumption of citrus fruits.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of AN2
                      Induced Change Naringenin concentration: increase (FC = 8.33)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of naringenin levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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