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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 is found in barley. Aesculetin is a metabolite of infected sweet potat
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
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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-22e400291639a7bbb33aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-22e400291639a7bbb33aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7k-0900000000-27f017ab7c2ce7d51594JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4091000000-75f069a0c45a2105bec7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-099787543429855740d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-7463290884843ecedfcdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0561-0900000000-51a6f720320ed2c06badJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-293c319b48c0eef0fc1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-1900000000-c1c544e7e6908455b35aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-055r-9600000000-ab9e766b7e2e6ca68e24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-55055a28076339d9e00cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-057i-0900000000-f1f7d3c5c646263fec5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-b32d205aa8377f348f32JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-c52a5a89a2694dc97b3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-84537a7c4f55946e6814JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-6fd1fa0c328428391896JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-01cff2483b03717e8be3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-df8ba2ed269c599a34fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05fr-1900000000-27b50b8924af5378d7b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-6e66bee9ed2657fcd00aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-55cc4447de7427b3e5e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-1b218d16bdf44f9f7e04JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-0900000000-f445625d24b1436ba21eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-96b92caac30fde152f75JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d2c3a55e9c5410dcf2c6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-4900000000-3333d8cac0ad0cd849ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-584e96c31f961d05b6d7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-5abbabd3e97d0592e369JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-bc43365ec40caf4ed6e9JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-6900000000-7b2a54b680eb0245558aJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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 ID639
FoodDB IDFDB002775
KNApSAcK IDC00002471
Chemspider ID4444764
KEGG Compound IDC09263
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAesculetin
METLIN IDNot Available
PubChem Compound5281416
PDB IDNot Available
ChEBI ID490095
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