Showing Compound Licochalcone B (FDB016340)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:22 UTC

Update date

2019-11-26 03:13:04 UTC

Primary ID

FDB016340

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Licochalcone B

Description

Licochalcone B belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, licochalcone b is considered to be a flavonoid. Licochalcone B has been detected, but not quantified in, several different foods, such as herbal tea, teas (Camellia sinensis), green tea, black tea, and herbs and spices. This could make licochalcone b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licochalcone B.

CAS Number

58749-23-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 3 of 3 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	3.17	ALOGPS
logP	2.82	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.28 m³·mol⁻¹	ChemAxon
Polarizability	29.52 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

C16H14O5

IUPAC name

(2E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

InChI Identifier

InChI=1S/C16H14O5/c1-21-16-11(5-9-14(19)15(16)20)4-8-13(18)10-2-6-12(17)7-3-10/h2-9,17,19-20H,1H3/b8-4+

InChI Key

DRDRYGIIYOPBBZ-XBXARRHUSA-N

Isomeric SMILES

COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

Classification

Description

Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retrochalcones

Alternative Parents

Substituents

Retrochalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Anisole
Benzoyl
Catechol
Methoxybenzene
Phenol ether
Aryl ketone
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Ether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120434 )

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 67.13%; H 4.93%; O 27.94%	DFC
Melting Point	Mp 195-197°	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	Licochalcone B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xr-2690000000-358dcbfa3ef3c89c6b8d	Spectrum
Predicted GC-MS	Licochalcone B, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-0001900000-dcef9c9a4d3d7beda21a	Spectrum
Predicted GC-MS	Licochalcone B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0930000000-e66ffb2c5d7bf56f571b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0930000000-db3da56b339271a7bace	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0uka-0900000000-ecea7b5e35d6a0033c7a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-f64407be17876dad151f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0190000000-1717e8fef49c860a66fc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0910000000-38b594f6092ab3d6cade	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0490000000-cd3ab1dc17d4a17a97df	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-5af3dba7415fbbef4e66	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ri-0970000000-1c965c89876c67e3c3cc	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-4900000000-1b3b1aeda1e725cdd1d9	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-c2652c467cc82725fd20	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0490000000-f6e00598644f89e80774	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01bc-5950000000-be797e2f0744297850f5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-47410b095ae44693234e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-1390000000-62e6742a1fbf9f08a234	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-4920000000-cb245567146abdcd29a3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-d30f02e34f4320b2aa52	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0076-2930000000-de7b822b51d0d1e215ba	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fu-5910000000-3943a7ba7c64e061b6d7	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4477423

ChEMBL ID

CHEMBL2437372

KEGG Compound ID

Not Available

Pubchem Compound ID

5318999

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB37320

CRC / DFC (Dictionary of Food Compounds) ID

BFK28-D:KQQ60-F

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00006938

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

Black tea	Expected but not quantified	Not Available	DFC CODES
Green tea	Expected but not quantified	Not Available	DFC CODES
Herbal tea	Expected but not quantified	Not Available	DFC CODES
Red tea	Expected but not quantified	Not Available	DFC CODES