General Information of MET (ID: META01221)
Name Naringin
Synonyms   Click to Show/Hide Synonyms of This Metabolite
naringin; 10236-47-2; Naringoside; Naringin hydrate; UNII-N7TD9J649B; Naringenin 7-O-neohesperidoside; Naringenine-7-rhamnosidoglucoside; 4'5-diOH-Flavone-7-rhgluc; CHEMBL451532; N7TD9J649B; CHEBI:28819; Naringenin 7-Rhamnoglucoside; C27H32O14; MFCD00148888; aurantiin; Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]; (S)-7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one; 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Source Aromatic heteropolycyclic compounds
Structure Type   Flavonoid glycosides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Phenylpropanoids and polyketides
Flavonoids
Flavonoid glycosides
PubChem CID
442428
HMDB ID
HMDB0002927
Formula
C27H32O14
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
C09789
ChEBI ID
28819
FooDB ID
FDB011866
ChemSpider ID
390868
METLIN ID
3604
Physicochemical Properties Molecular Weight 580.5 Topological Polar Surface Area 225
XlogP -0.5 Complexity 884
Heavy Atom Count 41 Rotatable Bond Count 6
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 14
Function
Naringin, also known as naringoside or naringin hydrate, belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. It is metabolized to the flavonone naringenin in humans. Naringin is an extremely weak basic (essentially neutral) compound (based on its pKa). Naringin is a bitter tasting compound. Outside of the human body, Naringin is found, on average, in the highest concentration within a few different foods, such as rosemaries, grapefruit/pummelo hybrids, and grapefruits and in a lower concentration in grape wines, pummelo, and beers. Naringin has also been detected, but not quantified in, several different foods, such as citrus, limes, herbs and spices, common oregano, and mandarin orange (clementine, tangerine). This could make naringin a potential biomarker for the consumption of these foods. Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro.
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 Naringin concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of naringin 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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