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Aesculin (FDB002776)

Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:10:37 UTC
Primary IDFDB002776
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAesculin
DescriptionAesculin 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. Aesculin is an extremely weak basic (essentially neutral) compound (based on its pKa). Aesculin is found, on average, in the highest concentration within beers. Aesculin has also been detected, but not quantified in, several different foods, such as lentils, sweet basils, mugworts, common beans, and chicories. This could make aesculin a potential biomarker for the consumption of these foods.
CAS Number531-75-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
Polarizability31.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H16O9
IUPAC name7-hydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
InChI IdentifierInChI=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
InChI KeyXHCADAYNFIFUHF-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(O)C=C3OC(=O)C=CC3=C2)C(O)C(O)C1O
Average Molecular Weight340.2821
Monoisotopic Molecular Weight340.07943211
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.95%; H 4.74%; O 42.32%DFC
Melting PointMp 205°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -77.5 (c, 3 in aq. dioxan)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAesculin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6947000000-19895b8b387f11d9179dSpectrum
Predicted GC-MSAesculin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2353029000-f90429c99944a173ba08Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002r-0809000000-a156a991511f00b65a772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-900b94103dde5ea786f42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-dead96eade01b822e1022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-d1089ced80e3aad1409b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-fd6b0737193a9669d0eb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00c0-0900000000-80c75412526e8c4c38392017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1729000000-b928bdec44f5d1346b352015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1911000000-16d7b3b8f15dd797da5c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-2900000000-46bb89536fc947bc66302015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0906000000-68762b523b2407ebaa2f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9a0d97a2a3f118d39d432015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1900000000-81ab23ab5df41a41c8da2015-04-24View Spectrum
NMRNot Available
ChemSpider ID4508522
ChEMBL IDNot Available
KEGG Compound IDC09264
Pubchem Compound ID5351506
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID640
DrugBank IDNot Available
HMDB IDHMDB30820
CRC / DFC (Dictionary of Food Compounds) IDCNP29-S:CNP31-N
EAFUS IDNot Available
Dr. Duke IDESCULIN|AESCULOSIDE|AESCULIN
BIGG IDNot Available
KNApSAcK IDC00002472
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAesculin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti acrocyanotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti aging52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti capillary-fragilityDUKE
anti cellulitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti CVSDUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti erythemic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti hemorrhoidal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti panniculopathicDUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti Raynaud's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti seborrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cholereticDUKE
cosmetic64857 The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hypertensiveDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
microvasculokineticDUKE
paralyticDUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
vasoprotectiveDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.