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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:14 UTC
Update Date2022-03-07 02:52:42 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 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?1600446268
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling Point469.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility72130 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.980 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available129.461http://allccs.zhulab.cn/database/detail?ID=AllCCS00001458
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.68631661259
DarkChem[M-H]-136.66231661259
DeepCCS[M+H]+134.12930932474
DeepCCS[M-H]-131.73330932474
DeepCCS[M-2H]-167.18130932474
DeepCCS[M+Na]+142.30930932474
AllCCS[M+H]+136.432859911
AllCCS[M+H-H2O]+131.932859911
AllCCS[M+NH4]+140.732859911
AllCCS[M+Na]+141.932859911
AllCCS[M-H]-133.732859911
AllCCS[M+Na-2H]-134.032859911
AllCCS[M+HCOO]-134.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AesculetinOC1=C(O)C=C2C=CC(=O)OC2=C13099.2Standard polar33892256
AesculetinOC1=C(O)C=C2C=CC(=O)OC2=C11856.8Standard non polar33892256
AesculetinOC1=C(O)C=C2C=CC(=O)OC2=C12061.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aesculetin,1TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=CC(=O)O2)C=C1O2083.7Semi standard non polar33892256
Aesculetin,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)OC(=O)C=C22075.3Semi standard non polar33892256
Aesculetin,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)OC(=O)C=C22128.1Semi standard non polar33892256
Aesculetin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CC(=O)O2)C=C1O2343.2Semi standard non polar33892256
Aesculetin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC(=O)C=C22323.4Semi standard non polar33892256
Aesculetin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(=O)C=C22603.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Aesculetin EI-B (Non-derivatized)splash10-004i-7900000000-22e400291639a7bbb33a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aesculetin EI-B (Non-derivatized)splash10-004i-7900000000-22e400291639a7bbb33a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aesculetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7k-0900000000-27f017ab7c2ce7d515942017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aesculetin GC-MS (2 TMS) - 70eV, Positivesplash10-00di-4091000000-75f069a0c45a2105bec72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aesculetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-6900000000-7b2a54b680eb0245558a2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-099787543429855740d52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-7463290884843ecedfcd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , negative-QTOFsplash10-0561-0900000000-51a6f720320ed2c06bad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-293c319b48c0eef0fc1f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , negative-QTOFsplash10-004i-1900000000-c1c544e7e6908455b35a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , negative-QTOFsplash10-055r-9600000000-ab9e766b7e2e6ca68e242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-55055a28076339d9e00c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , negative-QTOFsplash10-057i-0900000000-f1f7d3c5c646263fec5a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin Linear Ion Trap , negative-QTOFsplash10-0059-0900000000-b32d205aa8377f348f322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin Linear Ion Trap , negative-QTOFsplash10-0059-0900000000-c52a5a89a2694dc97b3f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-004i-0900000000-84537a7c4f55946e68142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-004i-0900000000-6fd1fa0c3284283918962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-01cff2483b03717e8be32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-df8ba2ed269c599a34fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-05fr-1900000000-27b50b8924af5378d7b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-6e66bee9ed2657fcd00a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-004i-1900000000-55cc4447de7427b3e5e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-004i-0900000000-1b218d16bdf44f9f7e042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aesculetin LC-ESI-QTOF , positive-QTOFsplash10-00e9-0900000000-f445625d24b1436ba21e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aesculetin 10V, Positive-QTOFsplash10-004i-0900000000-96b92caac30fde152f752016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aesculetin 20V, Positive-QTOFsplash10-004i-0900000000-d2c3a55e9c5410dcf2c62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aesculetin 40V, Positive-QTOFsplash10-0a4r-4900000000-3333d8cac0ad0cd849dd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aesculetin 10V, Negative-QTOFsplash10-004i-0900000000-584e96c31f961d05b6d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aesculetin 20V, Negative-QTOFsplash10-004i-0900000000-5abbabd3e97d0592e3692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aesculetin 40V, Negative-QTOFsplash10-001i-4900000000-bc43365ec40caf4ed6e92016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002775
KNApSAcK IDC00002471
Chemspider ID4444764
KEGG Compound IDC09263
BioCyc IDCPD-8097
BiGG IDNot Available
Wikipedia LinkAesculetin
METLIN IDNot Available
PubChem Compound5281416
PDB IDNot Available
ChEBI ID490095
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1242861
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