Showing Compound 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
6,7-Dihydroxy-2H-1-benzopyran-2-one	ChEBI
6,7-Dihydroxycoumarin	ChEBI
Cichorigenin	ChEBI
Cichoriin aglucon	ChEBI
Cichoriin aglycon	ChEBI
Esculin aglucon	ChEBI
Esculin aglycon	ChEBI
2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9ci)	HMDB
6,7-Dihydroxy-2-benzopyrone	HMDB
6,7-Dihydroxy-2H-chromen-2-one	HMDB
6,7-Dihydroxy-coumarin	HMDB
6,7-Dihydroxycoumarin, 8ci	HMDB
Aesculetin (cichorigenin	HMDB
Asculetine	HMDB
Coumarin, 6,7-dihydroxy- esculetin	HMDB
Esculetin	HMDB
Esculetol	HMDB
Esculetol)	HMDB
Aesculetin	ChEBI
2H-1-Benzopyran-2-one, 6,7-dihydroxy-	biospider
2H-1-Benzopyran-2-one, 6,7-dihydroxy- (9CI)	biospider
6,7-Dihydroxycoumarin, 8CI	db_source
CichorIIn aglucon	biospider
CichorIIn aglycon	biospider
Coumarin, 6, 7-dihydroxy-	biospider
Coumarin, 6,7-dihydroxy-	biospider
Coumarin, 6,7-dihydroxy- Esculetin	biospider
Esculatin	biospider
esculetol)	biospider

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	An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes.	DUKE
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Analgesic	35480	An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
Anti-arrhythmic	38070	An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.	DUKE
Anti-asthmatic	49167	An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti capillary-fragility		An agent that strengthens capillary walls to prevent rupture, reducing bruising and bleeding. It plays a biological role in maintaining vascular integrity, and has therapeutic applications in treating conditions like purpura and hemorrhoids, with key medical uses in preventing and managing microvascular damage.	DUKE
Anti dysenteric	52217	An agent that treats and prevents dysentery, reducing inflammation and diarrhea. It is used to manage bacterial, viral, or parasitic infections, and is commonly applied in treating gastrointestinal disorders, such as amoebic dysentery, and other intestinal infections.	DUKE
Anti-escherichic		An antibody binding to Escherichia-specific targets, playing a role in immune defense. Therapeutically, it is used to combat E. coli infections, with key medical applications in treating urinary tract infections, sepsis, and gastrointestinal diseases.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti pyretic	35493	An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-staphylococcic	33282	An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Cardiodepressant	38070	An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand.	DUKE
Choleretic		An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.	DUKE
Cosmetic	64857	A substance used to enhance physical appearance, with no therapeutic effect. It plays a social and psychological role, boosting self-esteem and confidence. Key uses include skincare, haircare, and makeup, with no direct medical applications, but can have indirect benefits such as improving mental well-being.	DUKE
Cytotoxic	52209	An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.	DUKE
Dermatitigenic		An agent that causes inflammation of the skin (dermatitis), triggering allergic reactions and immune responses. Its biological role involves activating immune cells, leading to skin irritation. Therapeutically, it is used to test skin sensitivity and develop treatments for dermatitis. Key medical uses include diagnosing skin allergies and researching dermatitis treatments.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Hepatoprotective	62868	An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.	DUKE
Hypertensive		An agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	DUKE
Musculotropic		An agent that acts on muscle tissue, stimulating muscle activity and contraction. It plays a biological role in regulating muscle tone and movement. Therapeutically, musculotropic agents are used to treat muscle weakness, paralysis, and atrophy, with key medical applications in neurology and physical medicine.	DUKE
Myorelaxant		An agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Prostaglandin synthesis inhibitor	35222	An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).	DUKE
Sunscreen	52217	A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders.	DUKE
UV-screen	52217	An agent that absorbs or blocks ultraviolet (UV) radiation, preventing skin damage and reducing risk of skin cancer. It plays a biological role in protecting skin from UV-induced harm. Therapeutically, UV-screens are used to prevent sunburn, photoaging, and skin cancer, with key medical applications in dermatology and preventive care.	DUKE
Xanthine oxidase inhibitor	35634	An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	CHEBI