AFCDB: Scopoletin (FDB012705)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:19 UTC

Update date

2020-09-17 15:39:57 UTC

Primary ID

FDB012705

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Scopoletin

Description

Scopoletin, also known as 6-methylesculetin or acid, gelseminic, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Scopoletin is an extremely weak basic (essentially neutral) compound (based on its pKa). Scopoletin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Scopoletin is found, on average, in the highest concentration within a few different foods, such as anises, oats, and sherries. Scopoletin has also been detected, but not quantified in, several different foods, such as barley, tarragons, mung beans, figs, and pepper (c. annuum). This could make scopoletin a potential biomarker for the consumption of these foods. A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6.

CAS Number

92-61-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	2.35 g/L	ALOGPS
logP	1.65	ALOGPS
logP	1.32	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.26	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.99 m³·mol⁻¹	ChemAxon
Polarizability	18.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H8O4

IUPAC name

7-hydroxy-6-methoxy-2H-chromen-2-one

InChI Identifier

InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3

InChI Key

RODXRVNMMDRFIK-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=C2OC(=O)C=CC2=C1

Average Molecular Weight

192.17

Monoisotopic Molecular Weight

192.042258738

Classification

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:17488 )
coumarins (C01752 )
a small molecule (SCOPOLETIN )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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 62.50%; H 4.20%; O 33.30%	DFC
Melting Point	Mp 204°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-002f-4900000000-b5bdf737b69c5cd7c5aa	2015-03-01	View Spectrum
GC-MS	Scopoletin, 1 TMS, GC-MS Spectrum	splash10-053r-2490000000-c200887014ff29ef3a8f	Spectrum
GC-MS	Scopoletin, non-derivatized, GC-MS Spectrum	splash10-053r-2490000000-c200887014ff29ef3a8f	Spectrum
GC-MS	Scopoletin, non-derivatized, GC-MS Spectrum	splash10-053r-1490000000-2146bc4f0afceba80b06	Spectrum
Predicted GC-MS	Scopoletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dj-0900000000-46efa588a7f66072d294	Spectrum
Predicted GC-MS	Scopoletin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-2290000000-2215044fdc455cf39861	Spectrum
Predicted GC-MS	Scopoletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-004i-0000092000-fe08120bacfe47df17f2	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0903000010-279e9ecfac68f75b37fd	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0903000010-279e9ecfac68f75b37fd	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0903000010-279e9ecfac68f75b37fd	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0006-0901000000-f56262960dba956afd50	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0uk9-0900000000-37644bdb4253d408730b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0903000010-279e9ecfac68f75b37fd	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004l-0900000000-0725f844ed58b7b3db24	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0900000000-f55cc5686f36a2c31bdf	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0092-0900000000-2371c5d87e204b2f3187	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0006-0901000000-f56262960dba956afd50	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0fh9-0900000000-9ee871d32b4eb22529b8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-94eacbe24073498f4dcc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-18a42b21822b016c32ce	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-1dd9600ca8db6c98239b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-c13de07771b151ebed9e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0uk9-0900000000-37644bdb4253d408730b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004l-0900000000-0725f844ed58b7b3db24	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0900000000-f55cc5686f36a2c31bdf	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-ce78be779b8108ca1e10	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-5364ea5b64704765d3f4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-1900000000-d4ccdf4b37aff5a77377	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-bd8785dd1cd0807268bd	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-8521e4d80e5fe256bb81	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o1-1900000000-aa4c65b1940903b4e3e6	2015-04-25	View Spectrum

NMR

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

17488

Phenol-Explorer ID

638

DrugBank ID

Not Available

HMDB ID

HMDB34344

CRC / DFC (Dictionary of Food Compounds) ID

HJZ66-A:HJZ66-A

EAFUS ID

Not Available

Dr. Duke ID

SCOPOLETOL|SCOPOLETIN

BIGG ID

Not Available

KNApSAcK ID

C00002499

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

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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
allelochemic			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
anesthetic			DUKE
anti adrenergic	37962	Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.	DUKE
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	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 bronchoconstrictor	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Showing 1 to 10 of 43 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

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.

Scopoletin (FDB012705)

Structure for FDB012705 (Scopoletin)