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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:14 UTC
Update Date2020-04-28 17:43:34 UTC
HMDB IDHMDB0030820
Secondary Accession Numbers
  • HMDB30820
Metabolite Identification
Common NameAesculin
DescriptionEsculin, 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.
Structure
Data?1588095814
Synonyms
ValueSource
6,7-Dihydroxycoumarin 6-glucosideChEBI
6,7-Dihydroxycoumarin-6-O-glucosideChEBI
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-oneChEBI
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarinChEBI
7-Hydroxy-6-glucosyloxy-2H-chromeneChEBI
AesculinChEBI
Esculetin 6-beta-D-glucosideChEBI
Esculetin 6-O-glucosideChEBI
EsculosideChEBI
6-(b-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-oneGenerator
6-(Β-D-glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-oneGenerator
6-(b-D-Glucopyranosyloxy)-7-hydroxy-cumarinGenerator
6-(Β-D-glucopyranosyloxy)-7-hydroxy-cumarinGenerator
Esculetin 6-b-D-glucosideGenerator
Esculetin 6-β-D-glucosideGenerator
VenoplantMeSH
(-)-EsculinHMDB
6-(beta-D-Glucopyranosyloxy)-7-hydroxycoumarinHMDB
6-(β-D-Glucopyranosyloxy)-7-hydroxycoumarinHMDB
EsculinHMDB
EsculineHMDB
Chemical FormulaC15H16O9
Average Molecular Weight340.284
Monoisotopic Molecular Weight340.079432095
IUPAC Name7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
Traditional Name(-)-esculin
CAS Registry Number531-75-9
SMILES
OC[C@H]1O[C@@H](OC2=C(O)C=C3OC(=O)C=CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1
InChI KeyXHCADAYNFIFUHF-TVKJYDDYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassCoumarin glycosides
Direct ParentCoumarin glycosides
Alternative Parents
Substituents
  • Coumarin o-glycoside
  • Coumarin-6-o-glycoside
  • Phenolic glycoside
  • 7-hydroxycoumarin
  • Hydroxycoumarin
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.3 g/LALOGPS
logP-0.53ALOGPS
logP-1.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)8.12ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.65 m³·mol⁻¹ChemAxon
Polarizability31.58 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0901000000-4baa83a9d2df1615a0bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-4321100129-8dd728a7ffce4137b185Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-f430c535996e7a3911ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0900000000-6f75f8f80ff5ba44b19aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0906000000-fcca2dd08f7f4a0caf8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-5de325332ddb75bc13b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-ed52db233670cc2482ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1729000000-69d359de90e6b4362837Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-918f71b3f7d771af124fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-2900000000-d9826b19b62d974318cdSpectrum
MSMass Spectrum (Electron Ionization)splash10-0fb9-8900000000-f07e5f4d396dfa02a8ecSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13155
Phenol Explorer Compound IDNot Available
FooDB IDFDB002776
KNApSAcK IDC00002472
Chemspider ID4444765
KEGG Compound IDC09264
BioCyc ID14461
BiGG IDNot Available
Wikipedia LinkAesculin
METLIN IDNot Available
PubChem Compound5281417
PDB IDNot Available
ChEBI ID4853
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Aesculin → 3,4,5-trihydroxy-6-[(2-oxo-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails