Showing Compound Isoliquiritigenin (FDB016335)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:22 UTC

Update date

2020-09-17 15:40:58 UTC

Primary ID

FDB016335

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isoliquiritigenin

Description

Isoliquiritigenin, also known as 6'-deoxychalcone or GU 17, belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, isoliquiritigenin is considered to be a flavonoid lipid molecule. Isoliquiritigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isoliquiritigenin is a bitter tasting compound. Outside of the human body, Isoliquiritigenin has been detected, but not quantified in, several different foods, such as java plums, tea leaf willows, sweet marjorams, common grapes, and black mulberries. This could make isoliquiritigenin a potential biomarker for the consumption of these foods. Isoliquiritigenin is a phenolic chemical compound found in licorice.

CAS Number

961-29-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(e)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenone	ChEBI
(e)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propene-1-one	ChEBI
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one	HMDB
2',4',4-Trihydroxychalcone	HMDB, MeSH
2',4',4-trihydroxychalcone	biospider
2',4'-Dihydroxy-3-(P-hydroxyphenyl)-acrylophenone	HMDB
2',4,4'-Trihydroxy-chalcone	HMDB
2',4,4'-Trihydroxychalcone	ChEBI
4,2',4'-Trihydroxychalcone	ChEBI

Showing 1 to 10 of 20 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.63	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.82 m³·mol⁻¹	ChemAxon
Polarizability	26.66 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

C15H12O4

IUPAC name

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

InChI Identifier

InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+

InChI Key

DXDRHHKMWQZJHT-FPYGCLRLSA-N

Isomeric SMILES

OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2)C=C1

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

Classification

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Benzoyl
Resorcinol
Styrene
Aryl ketone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

chalcones (CHEBI:310312 )
chalcones (C08650 )
Chalcones and dihydrochalcones (C08650 )
Chalcones and dihydrochalcones (LMPK12120096 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant:

Animal

Role

Industrial application:

Drug

Pharmaceutical industry:

Household products:

Antimicrobial agent

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 70.31%; H 4.72%; O 24.97%	DFC
Melting Point	Mp 200-204° (198-200°)	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	Isoliquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-1970000000-6164f65f5d6241a006f8	Spectrum
Predicted GC-MS	Isoliquiritigenin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-1034900000-76ae3aa74bffdff7ee01	Spectrum
Predicted GC-MS	Isoliquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isoliquiritigenin, 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	splash10-0a4i-0000009000-afd1640b539ec58a4616	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0000009000-afd1640b539ec58a4616	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014r-0900000000-e7c4095e90f57884e80c	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0090000000-788e4464b6a542aa7c22	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTOF , Positive	splash10-000i-0910000000-15db3efa5c81e3e8fc3e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014r-0900000000-e7c4095e90f57884e80c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0910000000-15db3efa5c81e3e8fc3e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-1930000000-6d143294fc9a6a343052	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 17V, positive	splash10-000j-0490000000-5d95d877601bf1780cf7	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 17V, positive	splash10-000j-0970000000-6f6553743b88b6c220e2	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-6646b871effe2fc1dec4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0790000000-a0a66b537f815a68529a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-1900000000-f6d8867bba0f74e95f4c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-001c-7900000000-d9f65201f86e97a92305	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000x-9600000000-4607845a4f3c870a8b7d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-1900000000-5b283194f8e6438d1cb4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0900000000-e7c4095e90f57884e80c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4r-0690000000-7996084c7a5f23179366	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-803b7c0679a83bac81f6	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-810f1a7ccbea17d944d3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052s-0960000000-9529b79414d923c90873	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ks-4910000000-f074bc6f0bf8212cf9cc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0290000000-a373dc716189e73d742c	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0690000000-12c68dfca23fb3e6405d	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-5910000000-ecfe8b4bdcef6eaa160e	2016-08-04	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

918

DrugBank ID

DB03285

HMDB ID

HMDB37316

CRC / DFC (Dictionary of Food Compounds) ID

KQQ39-F:KQQ39-F

EAFUS ID

Not Available

Dr. Duke ID

ISOLIQUIRITIGENIN

BIGG ID

Not Available

KNApSAcK ID

C00006925

HET ID

HCC

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

918

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
anti aggregant			DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ischemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti platelet aggregation factor	50427	A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.	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
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE