AFCDB: Aesculetin (FDB002775)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:31 UTC

Update date

2020-02-24 19:10:37 UTC

Primary ID

FDB002775

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Aesculetin

Description

Aesculetin, 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 sherry. Aesculetin has also been detected, but not quantified in, several different foods, such as mugworts (Artemisia vulgaris), highbush blueberries (Vaccinium corymbosum), grape wine, beer, and opium poppies (Papaver somniferum). This could make aesculetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Aesculetin.

CAS Number

305-01-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.6 g/L	ALOGPS
logP	1.38	ALOGPS
logP	1.18	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.51 m³·mol⁻¹	ChemAxon
Polarizability	16.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H6O4

IUPAC name

6,7-dihydroxy-2H-chromen-2-one

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 Key

ILEDWLMCKZNDJK-UHFFFAOYSA-N

Isomeric SMILES

OC1=C(O)C=C2C=CC(=O)OC2=C1

Average Molecular Weight

178.143

Monoisotopic Molecular Weight

178.026608673

Classification

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

6,7-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:490095 )
coumarins (C09263 )
a coumarin (CPD-8097 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 60.68%; H 3.39%; O 35.92%	DFC
Melting Point	Mp 270°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	353 (e 12000) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004i-6900000000-7b2a54b680eb0245558a	2015-03-01	View Spectrum
GC-MS	Aesculetin, non-derivatized, GC-MS Spectrum	splash10-004i-7900000000-22e400291639a7bbb33a	Spectrum
GC-MS	Aesculetin, non-derivatized, GC-MS Spectrum	splash10-004i-7900000000-22e400291639a7bbb33a	Spectrum
Predicted GC-MS	Aesculetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f7k-0900000000-27f017ab7c2ce7d51594	Spectrum
Predicted GC-MS	Aesculetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-4091000000-75f069a0c45a2105bec7	Spectrum
Predicted GC-MS	Aesculetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-099787543429855740d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-7463290884843ecedfcd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0561-0900000000-51a6f720320ed2c06bad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-293c319b48c0eef0fc1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-1900000000-c1c544e7e6908455b35a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-055r-9600000000-ab9e766b7e2e6ca68e24	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-55055a28076339d9e00c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-057i-0900000000-f1f7d3c5c646263fec5a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0059-0900000000-b32d205aa8377f348f32	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0059-0900000000-c52a5a89a2694dc97b3f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-84537a7c4f55946e6814	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-6fd1fa0c328428391896	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-01cff2483b03717e8be3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-df8ba2ed269c599a34fd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05fr-1900000000-27b50b8924af5378d7b0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0900000000-6e66bee9ed2657fcd00a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-1900000000-55cc4447de7427b3e5e0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-1b218d16bdf44f9f7e04	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00e9-0900000000-f445625d24b1436ba21e	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-96b92caac30fde152f75	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-d2c3a55e9c5410dcf2c6	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-4900000000-3333d8cac0ad0cd849dd	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-584e96c31f961d05b6d7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-5abbabd3e97d0592e369	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-4900000000-bc43365ec40caf4ed6e9	2016-08-03	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

639

DrugBank ID

Not Available

HMDB ID

HMDB30819

CRC / DFC (Dictionary of Food Compounds) ID

CNP29-S:CNP29-S

EAFUS ID

Not Available

Dr. Duke ID

ESCULETIN|AESCULETIN

BIGG ID

Not Available

KNApSAcK ID

C00002471

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
5-lipoxygenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
aldose reductase inhibitor	48550	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
analgesic	35480	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 arrhythmic	38070	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
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti capillary-fragility			DUKE
anti dysenteric	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti escherichic			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti mutagenic			DUKE
anti pyretic	35493	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 septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cardiodepressant	38070	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
choleretic			DUKE
cosmetic	64857	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
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
dermatitigenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hypertensive			DUKE
lipoxygenase inhibitor	35856	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
musculotropic			DUKE
myorelaxant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
sunscreen	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
UV-screen	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	DUKE
antioxidant	22586	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.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.

Aesculetin (FDB002775)

Structure for FDB002775 (Aesculetin)