AFCDB: Liquiritigenin (FDB000655)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:39 UTC

Update date

2019-11-26 02:55:09 UTC

Primary ID

FDB000655

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Liquiritigenin

Description

Liquiritigenin belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, liquiritigenin is considered to be a flavonoid. Liquiritigenin is a bitter tasting compound. Liquiritigenin has been detected, but not quantified in, several different foods, such as nuts, winged beans (Psophocarpus tetragonolobus), brussel sprouts (Brassica oleracea var. gemmifera), green vegetables, and prairie turnips (Pediomelum esculentum). This could make liquiritigenin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Liquiritigenin.

CAS Number

578-86-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.49	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.79	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.31 m³·mol⁻¹	ChemAxon
Polarizability	26.41 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

C15H12O4

IUPAC name

(2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2

InChI Key

FURUXTVZLHCCNA-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2

Average Molecular Weight

256.257

Monoisotopic Molecular Weight

256.073558866

Classification

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Chromone
Chromane
1-benzopyran
Benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavanone (CHEBI:28777 )
flavanones (C09762 )
Flavanones (LMPK12140061 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 70.31%; H 4.72%; O 24.97%	DFC
Melting Point	Mp 203-205°	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	[a]25D -36.2 (c, 0.09 in MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06vr-1290000000-473372a9cbd8aa299c8c	Spectrum
Predicted GC-MS	, 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 20V, Negative	splash10-014r-0900000000-8829ca13726fa5ef2894	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0090010000-4f0e0e7c69cd0563f154	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014r-0900000000-8829ca13726fa5ef2894	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QIT 4V, positive	splash10-0a4i-0090000000-e0ef2b922828538142d6	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QIT 15V, positive	splash10-01pa-0990000000-b55ccc74a2ff9f8ee58a	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4r-0690000000-e4eb8456793483d7e47b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-000i-0910000000-1b26412c239d13150a16	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQQ , positive	splash10-0a4i-0090000000-5a6df4ef73b17801c15b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 17V, positive	splash10-0a4r-0390000000-030c074282d57f882ea6	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 17V, positive	splash10-000j-0970000000-cc482ab502fe16da0b2c	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0900000000-8829ca13726fa5ef2894	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-7e114a20c600b4c23218	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2900000000-00ac566b03c0d20a16bc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014r-0900000000-37f3374e06351b592624	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-0910000000-afbe3e4c5fceeb057aac	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-1900000000-541af142929c530ffba1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0ap0-0970000000-5d4e47f2631f47124cc4	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-93474b44c5d1cb8cb155	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0790000000-572e47bb5dd6e39a5083	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00rj-5910000000-47c758a4f16f999867aa	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-b48d7117a74eb8dea54d	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0290000000-24d9ef16fb94c78f6cd9	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-6930000000-82d8508c6ca9b5e8be2a	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-74e7833e04a924835b1e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0790000000-f21efeafedd047dfaebd	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

1818

ChEMBL ID

Not Available

KEGG Compound ID

C09762

Pubchem Compound ID

1889

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB03601

HMDB ID

HMDB29519

CRC / DFC (Dictionary of Food Compounds) ID

BFK34-C:BFK72-M

EAFUS ID

Not Available

Dr. Duke ID

LIQUIRITIGENIN

BIGG ID

Not Available

KNApSAcK ID

C00000977

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

Liquiritigenin

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
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
central nervous system active	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hemoglobin inducer			DUKE
monoamine-oxidase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

Not Available

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.

Liquiritigenin (FDB000655)

Structure for FDB000655 (Liquiritigenin)