Licochalcone a

Details

• Internal ID: 7ae1a3a2-8dfe-4748-a821-e5c86daceee7
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retrochalcones
• IUPAC Name: (E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC(C)(C=C)C1=C(C=C(C(=C1)C=CC(=O)C2=CC=C(C=C2)O)OC)O
• SMILES (Isomeric): CC(C)(C=C)C1=C(C=C(C(=C1)/C=C/C(=O)C2=CC=C(C=C2)O)OC)O
• InChI: 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-DHZHZOJOSA-N
• Popularity: 244 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.47
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 58749-22-7
• Licochalcone-A
• LicochalconeA
• LICOAGROCHACONE A
• 3-Dimethylallyl-4,4'-dihydroxy-6-methoxychalcone
• (E)-3-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• (E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• CHEMBL139702
• UNII-JTV5467968
• JTV5467968
• 2-Propen-1-one, 3-(5-(1,1-dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-, (E)-
• (2E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• Licohalconel A
• Chalcone base + 2O, 1MeO, 1Prenyl or Licochalcone A (Not validated)
• D08GEN
• LICOCHALCONE A [MI]
• SCHEMBL114042
• LICOCHALCONE A [WHO-DD]
• DTXSID10904181
• CHEBI:125689
• CHEBI:174541
• KAZSKMJFUPEHHW-DHZHZOJOSA-N
• BCP08941
• EX-A1193
• HY-N0372
• BDBM50068270
• HSCI1_000078
• LMPK12120424
• MFCD01417903
• s7828
• AKOS026673964
• CCG-208030
• CS-5603
• Licochalcone A, >=96.0% (HPLC)
• (2E)-3-(5-(1,1-dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one
• (E)-3-[5-(1,1-dimethylallyl)-4-hydroxy-2-methoxy-phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• AC-34241
• AS-74730
• LS-122598
• L0261
• A902621
• Q-100677
• Q1644097
• BRD-K99667445-001-01-4
• (E)-3-[5-(1,1-Dimethyl-allyl)-4-hydroxy-2-methoxy-phenyl]-1-(4-hydroxy-phenyl)-propenone
• 3-[5-((E)-1,1-Dimethyl-allyl)-4-hydroxy-2-methoxy-phenyl]-1-(4-hydroxy-phenyl)-propenone
• (2E)-3-[5-(1,1-dimethyl-2-propen-1-yl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one
• 2-PROPEN-1-ONE, 3-(5-(1,1-DIMETHYL-2-PROPENYL)-4-HYDROXY-2-METHOXYPHENYL)-1-(4-HYDROXYPHENYL)-, (2E)-
• 2-Propen-1-one, 3-[5-(1,1-dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)- (E)-
• 2-Propen-1-one,3-[5-(1,1-dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-, (2E)-
• 3-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• 87080-27-1
• E)-3-[5-(1,1-Dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	+	0.7648	76.48%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8988	89.88%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.8522	85.22%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7427	74.27%
P-glycoprotein inhibitior	-	0.5300	53.00%
P-glycoprotein substrate	-	0.7497	74.97%
CYP3A4 substrate	+	0.5635	56.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8204	82.04%
CYP3A4 inhibition	+	0.6676	66.76%
CYP2C9 inhibition	-	0.5106	51.06%
CYP2C19 inhibition	+	0.7965	79.65%
CYP2D6 inhibition	-	0.8991	89.91%
CYP1A2 inhibition	+	0.7276	72.76%
CYP2C8 inhibition	+	0.8929	89.29%
CYP inhibitory promiscuity	+	0.6371	63.71%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.7249	72.49%
Carcinogenicity (trinary)	Non-required	0.6592	65.92%
Eye corrosion	-	0.9776	97.76%
Eye irritation	+	0.6655	66.55%
Skin irritation	-	0.8202	82.02%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3654	36.54%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7807	78.07%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.5373	53.73%
Acute Oral Toxicity (c)	III	0.7831	78.31%
Estrogen receptor binding	+	0.8878	88.78%
Androgen receptor binding	+	0.7080	70.80%
Thyroid receptor binding	+	0.8042	80.42%
Glucocorticoid receptor binding	+	0.7311	73.11%
Aromatase binding	+	0.8165	81.65%
PPAR gamma	+	0.6916	69.16%
Honey bee toxicity	-	0.8896	88.96%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	19100 nM; 19100 nM	IC50; IC50	PMID: 19632832; PMID: 21555221

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.14%	86.33%
CHEMBL3194	P02766	Transthyretin	95.24%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.53%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.46%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.19%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.00%	93.99%
CHEMBL2535	P11166	Glucose transporter	87.18%	98.75%
CHEMBL4208	P20618	Proteasome component C5	86.51%	90.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.97%	91.07%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.82%	89.62%
CHEMBL2581	P07339	Cathepsin D	83.96%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.96%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.36%	97.21%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.98%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	81.65%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	81.41%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.09%	92.94%
CHEMBL1255126	O15151	Protein Mdm4	81.05%	90.20%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.32%	95.50%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.14%	85.00%

Plants that contains it

• Euphorbia helioscopia
• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus
• Pogostemon cablin
• Spatholobus suberectus

Cross-Links

• PubChem: 5318998
• NPASS: NPC23870
• ChEMBL: CHEMBL139702
• LOTUS: LTS0018907
• wikiData: Q1644097