Details of Metabolite

General Information of MET (ID: META00833)
Name Isorhamnetin
Synonyms   Click to Show/Hide Synonyms of This Metabolite
3,5,7,4'-Tetrahydroxy-3'-methoxyflavone, '3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-benzopyran-4-one; 3-Methyl-quercetin; 3-Methylquercetin; Iso-rhamnetin; Isorhamnetine; Isorhamnetol', Quercetin 3'-methyl ether, 3'-Methoxy-3,4',5,7-tetrahydroxyflavone, 3'-Methoxyquercetin, 3'-Methylquercetin, 3'-O-Methylquercetin, 3,4',5,7-Tetrahydroxy-3'-methoxy-flavone, 3,4',5,7-Tetrahydroxy-3'-methoxyflavone, '3-Methylquercetine', 4'-Methoxyquercetin, 4'-Methylquercetin, 4'-O-Methylquercetin, '3-O-Methylquercetin
Source Food;Plant;Metabolite;Yeast Metabolite;Polyketides;Food;TCM Ingredients;Plant Metabolite; Microbial
Structure Type   Flavones  (Click to Show/Hide the Complete Structure Type Hierarchy)
Phenylpropanoids and polyketides
Flavonoids
Flavones
PubChem CID
5281654
HMDB ID
HMDB0002655
Formula
C16H12O7
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
C10084
ChEBI ID
6052
FooDB ID
FDB000604
ChemSpider ID
4444973
METLIN ID
3445
Physicochemical Properties Molecular Weight 316.26 Topological Polar Surface Area 116
XlogP 1.9 Complexity 503
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Function
Isorhamnetin is the methylated metabolite of quercetin. Quercetin is an important dietary flavonoid with in vitro antioxidant activity. However, it is found in human plasma as conjugates with glucuronic acid, sulfate or methyl groups, with no significant amounts of free quercetin present. Isorhamnetin prevents endothelial cell injuries from oxidized LDL via inhibition of lectin-like ox-LDL receptor-1 upregulation, interference of ox-LDL-mediated intracellular signaling pathway (p38MAPK activation, NF-kappaB nuclear translocation, eNOS expression) and the antioxidant activity of isorhamnetin. Isorhamnetin prevents endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II. Isorhamnetin appears to be a potent drug against esophageal cancer due to its in vitro potential to not only inhibit proliferation but also induce apoptosis of Eca-109 cells.
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 Isorhamnetin concentration: increase (FC = 44407.41)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of isorhamnetin 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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