Showing Compound Licocoumarone (FDB018169)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:33 UTC

Update date

2019-11-26 03:15:48 UTC

Primary ID

FDB018169

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Licocoumarone

Description

Licocoumarone belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, licocoumarone is considered to be a flavonoid. Licocoumarone has been detected, but not quantified in, herbs and spices. This could make licocoumarone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licocoumarone.

CAS Number

118524-14-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-(2',4'-Dihydroxyphenyl)-6-hydroxy-5-isopentenyl-4-methoxybenzofuran	ChEBI
2-(3,4-Dihydroxyphenyl)-6-hydroxy-4-methoxy-5-prenylbenzofuran	HMDB
4-[6-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)-2-benzofuranyl]-1,3-benzenediol, 9ci	HMDB
4-[6-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)-2-benzofuranyl]-1,3-benzenediol, 9CI	db_source
Benzyl(2-hydroxyethyl)dimethylammonium hydroxide	HMDB
Benzyl(2-hydroxyethyl)dimethylammonium Hydroxide	biospider
Benzyl(2-hydroxyethyl)dimethylammonium, hydroxide	HMDB
Licocoumarone	db_source

Showing 1 to 8 of 8 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.081 g/L	ALOGPS
logP	4.1	ALOGPS
logP	4.36	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.56 m³·mol⁻¹	ChemAxon
Polarizability	37.42 Å³	ChemAxon
Number of Rings	3	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

C20H20O5

IUPAC name

4-[6-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]benzene-1,3-diol

InChI Identifier

InChI=1S/C20H20O5/c1-11(2)4-6-14-17(23)10-19-15(20(14)24-3)9-18(25-19)13-7-5-12(21)8-16(13)22/h4-5,7-10,21-23H,6H2,1-3H3

InChI Key

CNPMAFLUEHEXRE-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(O2)C1=C(O)C=C(O)C=C1

Average Molecular Weight

340.3698

Monoisotopic Molecular Weight

340.13107375

Classification

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
2-phenylbenzofuran
Phenylbenzofuran
Benzofuran
Resorcinol
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:69098 )
1-benzofurans (CHEBI:69098 )
resorcinols (CHEBI:69098 )
Other Flavonoids (LMPK12160045 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

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 70.58%; H 5.92%; O 23.50%	DFC
Melting Point	Mp 183-185°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Licocoumarone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004m-3059000000-688c32ebe43ea76cf897	Spectrum
Predicted GC-MS	Licocoumarone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-1000390000-b4ea00a39182594312f9	Spectrum
Predicted GC-MS	Licocoumarone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-000i-0958000000-99f252fd7a8eaa4f7118	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000e-0956000000-590eda897b2930c2042d	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0029000000-a068dcf2e78877d3d832	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ko-4098000000-3107dca3fc1a784235dc	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-6290000000-1967f6e59e9faf6d8e1b	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-1dc3540c6ad04b9c34f6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0029000000-d066c3dd39217ce0a3d5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3893000000-38241922e6c8195688dc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-fd63e399cebf431bd289	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-0059000000-33c2bcc8160b1f5289d3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0397000000-7dab7e62d2cd0a2825cf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-0069000000-8eb83bb6b0434d4cd3fa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0091000000-847c3f386a48a6575631	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-0091000000-4757bed94e115d81f1f9	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

439849

ChEMBL ID

CHEMBL611368

KEGG Compound ID

Not Available

Pubchem Compound ID

503731

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38755

CRC / DFC (Dictionary of Food Compounds) ID

JVN94-B:LHF42-Y

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00010076

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

Not Available

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

Showing Compound Licocoumarone (FDB018169)

Structure for FDB018169 (Licocoumarone)