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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:14 UTC
Update Date2021-09-14 15:44:45 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?1600463426
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 Molecular Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Aesculin,1TMS,#13104.4324https://arxiv.org/abs/1905.12712
Aesculin,1TMS,#23211.0652https://arxiv.org/abs/1905.12712
Aesculin,1TMS,#33125.4136https://arxiv.org/abs/1905.12712
Aesculin,1TMS,#43112.4426https://arxiv.org/abs/1905.12712
Aesculin,1TMS,#53099.124https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#13052.037https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#23004.5337https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#33027.5908https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#43014.7568https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#53099.2725https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#63112.0645https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#73112.963https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#83052.4219https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#93049.411https://arxiv.org/abs/1905.12712
Aesculin,2TMS,#103045.7427https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#13018.2107https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#23032.7312https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#33026.6504https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#43016.5972https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#53048.402https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#63015.2983https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#73077.6157https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#83086.6306https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#93082.921https://arxiv.org/abs/1905.12712
Aesculin,3TMS,#103053.1426https://arxiv.org/abs/1905.12712
Aesculin,4TMS,#13053.1382https://arxiv.org/abs/1905.12712
Aesculin,4TMS,#23072.318https://arxiv.org/abs/1905.12712
Aesculin,4TMS,#33058.9155https://arxiv.org/abs/1905.12712
Aesculin,4TMS,#43065.3296https://arxiv.org/abs/1905.12712
Aesculin,4TMS,#53112.188https://arxiv.org/abs/1905.12712
Aesculin,5TMS,#13116.5603https://arxiv.org/abs/1905.12712
Aesculin,1TBDMS,#13371.5488https://arxiv.org/abs/1905.12712
Aesculin,1TBDMS,#23474.096https://arxiv.org/abs/1905.12712
Aesculin,1TBDMS,#33392.7532https://arxiv.org/abs/1905.12712
Aesculin,1TBDMS,#43381.007https://arxiv.org/abs/1905.12712
Aesculin,1TBDMS,#53365.3745https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#13625.1152https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#23602.6423https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#33581.912https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#43589.8508https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#53630.5247https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#63646.4302https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#73648.898https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#83583.1653https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#93581.605https://arxiv.org/abs/1905.12712
Aesculin,2TBDMS,#103564.465https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#13832.5095https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#23815.5725https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#33818.1682https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#43771.3335https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#53800.3926https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#63771.294https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#73817.3772https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#83830.3235https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#93836.6296https://arxiv.org/abs/1905.12712
Aesculin,3TBDMS,#103772.077https://arxiv.org/abs/1905.12712
Aesculin,4TBDMS,#13969.7598https://arxiv.org/abs/1905.12712
Aesculin,4TBDMS,#24003.1292https://arxiv.org/abs/1905.12712
Aesculin,4TBDMS,#33981.8652https://arxiv.org/abs/1905.12712
Aesculin,4TBDMS,#43962.9517https://arxiv.org/abs/1905.12712
Aesculin,4TBDMS,#53979.8633https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
MSMass Spectrum (Electron Ionization)splash10-0fb9-8900000000-f07e5f4d396dfa02a8ec2015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0901000000-4baa83a9d2df1615a0bb2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-4321100129-8dd728a7ffce4137b1852017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-f430c535996e7a3911ce2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0900000000-6f75f8f80ff5ba44b19a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-0c862135d78b959b4abe2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004r-0908000000-177773495a19980d69d02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-d70b32850e66c99a96d42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-837775bdf14ed0452f312021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-7c8f6419a5f9420de8ef2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004r-0908000000-d469bcf29ca978026b0e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-6b53852a3684b65f81d72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-2773ec1f085873c5d4f02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0920000000-d180ec16c9dce64bdcdb2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0906000000-fcca2dd08f7f4a0caf8f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-5de325332ddb75bc13b42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-ed52db233670cc2482ce2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1729000000-69d359de90e6b43628372016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-918f71b3f7d771af124f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-2900000000-d9826b19b62d974318cd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0509000000-43a22ceecb1b809212472021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1933000000-0f13e5e4afefacb9a7f62021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bi-2900000000-759fb491f32d54853de12021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0309000000-b68bdb38f4fa50a4ee6a2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1913000000-06b4c2a8c108978f5e932021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ba-1900000000-052735e33da6f9e2fdfb2021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2015-03-01View Spectrum
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 IDCPD-14461
BiGG IDNot Available
Wikipedia LinkAesculin
METLIN IDNot Available
PubChem Compound5281417
PDB IDNot Available
ChEBI ID4853
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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