Licochalcone A (CED0005684)

Record Information

Version

1.0

Creation Date

2016-05-25 20:55:24 UTC

Update Date

2026-04-15 16:40:43 UTC

SynCED ID

CED0005684

Secondary Accession Numbers

CHEM023240

Identification

Common Name

Licochalcone A

Class

Small Molecule

Description

Licochalcone A is an organic compound with the formula C21H22O4 and an average molecular weight of 338.40 g/mol. Licochalcone A belongs to the chalcones and dihydrochalcones, a subclass of linear 1,3-diarylpropanoids within the organic compounds. This compound is found in or released from one recorded source: food, food processing & cookware, specifically in the preparation of vinegar. Regarding its biological activity, Licochalcone A is recorded as an inhibitor of the protein target tyrosine-protein phosphatase non-receptor type 1 (PTPN1).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Dimethylallyl-4,4'-dihydroxy-6-methoxychalcone	HMDB
3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one, 9ci	HMDB
5-(1,1-Dimethylallyl)-4,4'-dihydroxy-2-methoxychalcone	HMDB
Licochalcone-a, synthetic	HMDB

Chemical Formula

C₂₁H₂₂O₄

Average Molecular Mass

338.397 g/mol

Monoisotopic Mass

338.152 g/mol

CAS Registry Number

58749-22-7

IUPAC Name

(2Z)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2Z)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

SMILES

COC1=C(\C=C/C(=O)C2=CC=C(O)C=C2)C=C(C(O)=C1)C(C)(C)C=C

InChI Identifier

InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8-

InChI Key

KAZSKMJFUPEHHW-FLIBITNWSA-N

Chemical Taxonomy

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
Phenylpropane
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Aryl ketone
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

aryl hydrocarbon receptor antagonist (PMC4951797 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	4.74	ALOGPS
logP	4.81	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.83	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	6	ChemAxon
Refractivity	100.61 m³·mol⁻¹	ChemAxon
Polarizability	36.94 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00di-2139000000-dd5ce01349b0a049596e	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-014i-1200900000-6f056fe7ac8d0f676d66	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0119000000-0a51f40550ed5ec31662	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0g4r-6988000000-1d8184f09c04ea1287d1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gi0-9620000000-6ed095cd55530005bea4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0119000000-da11738b507a0d3c769b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kr-1349000000-d3626b47e8fe11710eb4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-7891000000-b2d96245724d0ae4c02e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-58aebbe019e7e30272d1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1039000000-773f8a1d35597143325d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f79-2295000000-0ebd8672ece561c84e5d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0019000000-136e9e17a9180600a645	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-1494000000-55b38967e7349c9cae58	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-4941000000-9242418bf60def323fc9	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2785.0 Log mg/kg [1600:5000]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
inflammation	Has Therapeutic Effect On	Not Available	Not Available	PMC12756833
kidney disease	Not Available	Not Available	A urinary system disease that is located in the kidney. (DO)	PMC12678090
osteoarthritis	Has Therapeutic Effect On	Not Available	An arthritis that has material basis in worn out cartilage located in joint. (DO)	PMC11047486
Oxidative Stress	Has Therapeutic Effect On	Not Available	Not Available	PMC12756833
Drug Resistance, Multiple	Has Therapeutic Effect On	Not Available	Not Available	PMC8234180
renal carcinoma	Has Therapeutic Effect On	Not Available	Not Available	PMC12678090

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000548	Preparation Of Vinegar?Vinegar is produced through the fermentation of ethanol by acetic acid bacteria, resulting in a solution that typically contains 4-8% acetic acid.	Food, food processing & cookware	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000612	Body Washing Or Cleaning Implements?Body washing or cleaning implements, such as synthetic sponges, loofahs, and washcloths, can be sources of synthetic chemical contamination due to the materials used in their production.	Personal care & cosmetics	PubChem
CEDs000613	Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000616	Face Mask Cosmetics?Face mask cosmetics often contain a variety of synthetic chemicals, including preservatives, emulsifiers, and fragrances, which can contribute to chemical contamination.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem
CEDs02846	Sunscreens	Personal care & cosmetics	PMC12756833

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Broad substrate specificity ATP-binding cassette transporter ABCG2	Q9UNQ0	Humans	Predicted (SEA)	Prediction Confidence Score 0.505 Applicability Domain 1.0 Statistical Significance 7.00e-04 Supporting Reference Compounds 126 E-value 5.44945
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.472 Applicability Domain 1.0 Statistical Significance 0.0071 Supporting Reference Compounds 1538 E-value 55.2729
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	Prediction Confidence Score 0.393 Applicability Domain 0.426 Statistical Significance 0.0068 Supporting Reference Compounds 315 E-value 52.9375
Click to view 3D structure	Tissue factor	P13726	Humans	Predicted (SEA)	Prediction Confidence Score 0.381 Applicability Domain 0.442 Statistical Significance 0.0012 Supporting Reference Compounds 29 E-value 9.41976
Click to view 3D structure	Cytochrome P450 1B1	Q16678	Humans	Predicted (SEA)	Prediction Confidence Score 0.372 Applicability Domain 0.448 Statistical Significance 0.0027 Supporting Reference Compounds 88 E-value 20.8636
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P12527	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.421 Statistical Significance 0.0023 Supporting Reference Compounds 78 E-value 17.8275
Click to view 3D structure	Succinate-semialdehyde dehydrogenase, mitochondrial	P51649	Humans	Predicted (SEA)	Prediction Confidence Score 0.362 Applicability Domain 0.362 Statistical Significance 7.00e-05 Supporting Reference Compounds 1 E-value 0.544945
Click to view 3D structure	Transcription factor p65	Q04207	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.358 Applicability Domain 0.358 Statistical Significance 2.50e-04 Supporting Reference Compounds 1 E-value 1.94623
Click to view 3D structure	Cytochrome P450 1A1	P04798	Humans	Predicted (SEA)	Prediction Confidence Score 0.354 Applicability Domain 0.448 Statistical Significance 0.0026 Supporting Reference Compounds 77 E-value 20.3965
Click to view 3D structure	Stromal cell-derived factor 1	P48061	Humans	Predicted (SEA)	Prediction Confidence Score 0.34 Applicability Domain 0.421 Statistical Significance 6.90e-04 Supporting Reference Compounds 9 E-value 5.3716
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P07943	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.373 Statistical Significance 0.0029 Supporting Reference Compounds 70 E-value 22.4206
Click to view 3D structure	UDP-glucuronosyltransferase 1A1	P22309	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 1.0 Statistical Significance 1.50e-04 Supporting Reference Compounds 21 E-value 1.16774
Click to view 3D structure	Gag-Pol polyprotein	Q7ZJM1	Human immunodeficiency virus 1	Predicted (SEA)	Prediction Confidence Score 0.328 Applicability Domain 0.404 Statistical Significance 0.0036 Supporting Reference Compounds 96 E-value 28.2593
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.328 Applicability Domain 0.362 Statistical Significance 0.0682 Supporting Reference Compounds 1245 E-value 530.62
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.326 Applicability Domain 0.386 Statistical Significance 0.0262 Supporting Reference Compounds 472 E-value 204.354
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	Prediction Confidence Score 0.326 Applicability Domain 0.386 Statistical Significance 0.0224 Supporting Reference Compounds 407 E-value 174.149
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.325 Applicability Domain 0.362 Statistical Significance 0.0565 Supporting Reference Compounds 1130 E-value 439.848
Click to view 3D structure	Transcription factor EB	P19484	Humans	Predicted (SEA)	Prediction Confidence Score 0.321 Applicability Domain 0.321 Statistical Significance 7.90e-04 Supporting Reference Compounds 1 E-value 6.15009
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	Prediction Confidence Score 0.321 Applicability Domain 0.385 Statistical Significance 0.0133 Supporting Reference Compounds 241 E-value 103.306
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P09917	Humans	Predicted (SEA)	Prediction Confidence Score 0.318 Applicability Domain 0.369 Statistical Significance 0.0084 Supporting Reference Compounds 182 E-value 65.549
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	Prediction Confidence Score 0.317 Applicability Domain 0.362 Statistical Significance 0.044 Supporting Reference Compounds 825 E-value 342.692
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	Prediction Confidence Score 0.316 Applicability Domain 0.362 Statistical Significance 0.0469 Supporting Reference Compounds 793 E-value 365.424
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	Prediction Confidence Score 0.312 Applicability Domain 0.377 Statistical Significance 0.0096 Supporting Reference Compounds 109 E-value 75.1245
Click to view 3D structure	Xanthine dehydrogenase/oxidase	P80457	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.305 Applicability Domain 0.404 Statistical Significance 0.0027 Supporting Reference Compounds 29 E-value 20.7857
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	Prediction Confidence Score 0.304 Applicability Domain 0.323 Statistical Significance 0.0144 Supporting Reference Compounds 172 E-value 112.492