General Information of MET (ID: META01230)
Name Esculin
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Esculin; aesculin; 531-75-9; Esculoside; Esculin hydrate; (-)-Esculin; Polychrome; 6,7-Dihydroxycoumarin-6-O-glucoside; Bicolorin; Crataegin; Esculine; Esculetin 6-O-glucoside; 6,7-Dihydroxycoumarin 6-glucoside; UNII-1Y1L18LQAF; Vitamin C2; Esculetin 6-beta-D-glucoside; 6-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarin; CHEBI:4853; 7-Hydroxy-6-cumarinyl-glucosid; 6-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one; 1Y1L18LQAF; Polychrom
Source Aromatic heteropolycyclic compounds
Structure Type   Coumarin glycosides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Phenylpropanoids and polyketides
Coumarins and derivatives
Coumarin glycosides
PubChem CID
5281417
HMDB ID
HMDB0030820
Formula
C15H16O9
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
C09264
DrugBank ID
DB13155
ChEBI ID
4853
FooDB ID
FDB002776
ChemSpider ID
4444765
Physicochemical Properties Molecular Weight 340.28 Topological Polar Surface Area 146
XlogP -0.6 Complexity 495
Heavy Atom Count 24 Rotatable Bond Count 3
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 9
Function
Esculin, also known as esculoside, belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. As a result, a total of 19 metabolites (10 phase I metabolites and 9 phase II metabolites) were found and identified. Esculin is an extremely weak basic (essentially neutral) compound (based on its pKa). The main activities of Esculine focus on capillary protection, as it improves capillary permeability and fragility. The antioxidant property might as well explain some of the anti-inflammatory activity of the product, making it a suitable product for after sun treatments, for example. After oral administration of esculin (100 mg/kg) for rats, plasma, urine, feces and bile samples were collected to screen metabolites. Esculine also showed good antioxidant properties, protecting triglycerides against auto-oxidation at high temperatures . Topically applied Esculine increases the capillary density (the number of capillaries open to flow per surface unit) and improves the morphological aspect of the smallest blood vessels. It was also found that after oral administration of esculin, the esculin could be metabolized to esculetin in vivo via deglycosylation, and esculetin was found in all biological samples. It is reported to inhibit catabolic enzymes such as hyaluronidase and collagenase, thus preserving the integrity of the perivascular connective tissue.
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 Esculin concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of esculin 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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