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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:14 UTC
Update Date2019-07-23 06:07:23 UTC
HMDB IDHMDB0030819
Secondary Accession Numbers
  • HMDB30819
Metabolite Identification
Common NameAesculetin
DescriptionAesculetin, also known as cichorigenin or cichoriin aglucon, belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively. Aesculetin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Aesculetin is found, on average, in the highest concentration within sherries. Aesculetin has also been detected, but not quantified in, several different foods, such as horseradish, carrots, dandelions, grape wines, and highbush blueberries. This could make aesculetin a potential biomarker for the consumption of these foods.
Structure
Data?1563862043
Synonyms
ValueSource
6,7-Dihydroxy-2H-1-benzopyran-2-oneChEBI
6,7-DihydroxycoumarinChEBI
CichorigeninChEBI
Cichoriin agluconChEBI
Cichoriin aglyconChEBI
Esculin agluconChEBI
Esculin aglyconChEBI
2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9ci)HMDB
6,7-Dihydroxy-2-benzopyroneHMDB
6,7-Dihydroxy-2H-chromen-2-oneHMDB
6,7-Dihydroxy-coumarinHMDB
6,7-Dihydroxycoumarin, 8ciHMDB
Aesculetin (cichorigeninHMDB
AsculetineHMDB
Coumarin, 6,7-dihydroxy- esculetinHMDB
EsculetinHMDB
EsculetolHMDB
Esculetol)HMDB
AesculetinChEBI
Chemical FormulaC9H6O4
Average Molecular Weight178.143
Monoisotopic Molecular Weight178.026608673
IUPAC Name6,7-dihydroxy-2H-chromen-2-one
Traditional Nameesculetin
CAS Registry Number305-01-1
SMILES
OC1=C(O)C=C2C=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
InChI KeyILEDWLMCKZNDJK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6,7-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at positions 6 and 7 of the coumarin skeleton, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent6,7-dihydroxycoumarins
Alternative Parents
Substituents
  • 6,7-dihydroxycoumarin
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.6 g/LALOGPS
logP1.38ALOGPS
logP1.18ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.51 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-22e400291639a7bbb33aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-22e400291639a7bbb33aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7k-0900000000-27f017ab7c2ce7d51594Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4091000000-75f069a0c45a2105bec7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-099787543429855740d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-7463290884843ecedfcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0561-0900000000-51a6f720320ed2c06badSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-293c319b48c0eef0fc1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-1900000000-c1c544e7e6908455b35aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-055r-9600000000-ab9e766b7e2e6ca68e24Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-55055a28076339d9e00cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-057i-0900000000-f1f7d3c5c646263fec5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-b32d205aa8377f348f32Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-c52a5a89a2694dc97b3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-84537a7c4f55946e6814Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-6fd1fa0c328428391896Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-01cff2483b03717e8be3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-df8ba2ed269c599a34fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fr-1900000000-27b50b8924af5378d7b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-6e66bee9ed2657fcd00aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-55cc4447de7427b3e5e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-1b218d16bdf44f9f7e04Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-0900000000-f445625d24b1436ba21eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-96b92caac30fde152f75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d2c3a55e9c5410dcf2c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-4900000000-3333d8cac0ad0cd849ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-584e96c31f961d05b6d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-5abbabd3e97d0592e369Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-bc43365ec40caf4ed6e9Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-6900000000-7b2a54b680eb0245558aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002775
KNApSAcK IDC00002471
Chemspider IDNot Available
KEGG Compound IDC09263
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAesculetin
METLIN IDNot Available
PubChem Compound5281416
PDB IDNot Available
ChEBI ID490095
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
Aesculetin → 3,4,5-trihydroxy-6-[(7-hydroxy-2-oxo-2H-chromen-6-yl)oxy]oxane-2-carboxylic aciddetails
Aesculetin → 3,4,5-trihydroxy-6-[(6-hydroxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails