Showing Compound Aesculin (FDB002776)

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

FDB002776

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Aesculin

Description

Aesculin belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Aesculin is an extremely weak basic (essentially neutral) compound (based on its pKa). Aesculin is found, on average, in the highest concentration within beers. Aesculin has also been detected, but not quantified in, several different foods, such as lentils, sweet basils, mugworts, common beans, and chicories. This could make aesculin a potential biomarker for the consumption of these foods.

CAS Number

531-75-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
6,7-Dihydroxycoumarin 6-glucoside	HMDB
Aesculin	db_source
Bicolorin	HMDB
Crataegin	HMDB
Enallachrome	HMDB
Escosyl	HMDB
Esculetin 6-b-D-glucoside	HMDB
Esculetin 6-beta-D-glucoside	HMDB
Esculetin 6-O-glucoside	HMDB
Esculetin 6-β-D-glucoside	biospider

Showing 1 to 10 of 16 entries

Predicted Properties

Property	Value	Source
Water Solubility	10.3 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-1.1	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.65 m³·mol⁻¹	ChemAxon
Polarizability	31.59 Å³	ChemAxon
Number of Rings	3	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

C15H16O9

IUPAC name

7-hydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

InChI Identifier

InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2

InChI Key

XHCADAYNFIFUHF-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(OC2=C(O)C=C3OC(=O)C=CC3=C2)C(O)C(O)C1O

Average Molecular Weight

340.2821

Monoisotopic Molecular Weight

340.07943211

Classification

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin o-glycoside
Coumarin-6-o-glycoside
Phenolic glycoside
7-hydroxycoumarin
Hydroxycoumarin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Oxane
Benzenoid
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-11682 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 52.95%; H 4.74%; O 42.32%	DFC
Melting Point	Mp 205°	DFC
Optical Rotation	[a]D -77.5 (c, 3 in aq. dioxan)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Aesculin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6947000000-19895b8b387f11d9179d	Spectrum
Predicted GC-MS	Aesculin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-2353029000-f90429c99944a173ba08	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002r-0809000000-a156a991511f00b65a77	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-900b94103dde5ea786f4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-dead96eade01b822e102	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0900000000-d1089ced80e3aad1409b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-fd6b0737193a9669d0eb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00c0-0900000000-80c75412526e8c4c3839	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-1729000000-b928bdec44f5d1346b35	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1911000000-16d7b3b8f15dd797da5c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-2900000000-46bb89536fc947bc6630	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0906000000-68762b523b2407ebaa2f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-9a0d97a2a3f118d39d43	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1900000000-81ab23ab5df41a41c8da	2015-04-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4508522

ChEMBL ID

Not Available

KEGG Compound ID

C09264

Pubchem Compound ID

5351506

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

640

DrugBank ID

Not Available

HMDB ID

HMDB30820

CRC / DFC (Dictionary of Food Compounds) ID

CNP29-S:CNP31-N

EAFUS ID

Not Available

Dr. Duke ID

ESCULIN|AESCULOSIDE|AESCULIN

BIGG ID

Not Available

KNApSAcK ID

C00002472

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

Aesculin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
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 acrocyanotic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti aging	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti alopecic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti capillary-fragility			DUKE
anti cellulitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti CVS			DUKE
anti dermatitic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE