Licochalcone C

Details

• Internal ID: 5c70bfac-ad33-4183-b1d5-7aac3d9afa96
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retrochalcones
• IUPAC Name: (E)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1OC)C=CC(=O)C2=CC=C(C=C2)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1OC)/C=C/C(=O)C2=CC=C(C=C2)O)O)C
• InChI: InChI=1S/C21H22O4/c1-14(2)4-11-18-20(24)13-8-16(21(18)25-3)7-12-19(23)15-5-9-17(22)10-6-15/h4-10,12-13,22,24H,11H2,1-3H3/b12-7+
• InChI Key: WBDNTJSRHDSPSR-KPKJPENVSA-N
• Popularity: 15 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): 4.51
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 144506-14-9
• LicochalconeC
• Licochalcone c [MI]
• UNII-P1H7W3812O
• CHEMBL141207
• P1H7W3812O
• (E)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• (2E)-3-(4-Hydroxy-2-methoxy-3-(3-methyl-2-butenyl)phenyl)-1-(4-hydroxyphenyl)-2-propen-1-one
• 2-Propen-1-one, 3-(4-hydroxy-2-methoxy-3-(3-methyl-2-butenyl)phenyl)-1-(4-hydroxyphenyl)-, (2E)-
• 2-Propen-1-one, 3-(4-hydroxy-2-methoxy-3-(3-methyl-2-butenyl)phenyl)-1-(4-hydroxyphenyl)-, (E)-
• Chalcone base + 2O, 1MeO, 1Prenyl
• Licochalcone-C
• SCHEMBL7194029
• DTXSID40162737
• HY-N0374
• BDBM50301046
• LMPK12120423
• AKOS030573587
• AC-34243
• MS-25151
• 4,4'-Dihydroxy-2-methoxy-3-prenylchalcone
• CS-0008919
• A14848
• EN300-6499180
• EN300-6512984
• Q27286010
• Z2312381236
• 3-(4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• ((2E)-3-(4-hydroxy-2-methoxy-3-(3-methyl-2-butenyl) phenyl)-1-(4-hydroxyphenyl) -2-propen-1-one
• (2E)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• (E)-3-[4-Hydroxy-2-methoxy-3-(3-methyl-but-2-enyl)-phenyl]-1-(4-hydroxy-phenyl)-propenone
• 3-[4-HYDROXY-2-METHOXY-3-(3-METHYLBUT-2-EN-1-YL)PHENYL]-1-(4-HYDROXYPHENYL)PROP-2-EN-1-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.8079	80.79%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8411	84.11%
OATP2B1 inhibitior	-	0.7126	71.26%
OATP1B1 inhibitior	+	0.8636	86.36%
OATP1B3 inhibitior	+	0.8765	87.65%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8599	85.99%
P-glycoprotein inhibitior	-	0.4341	43.41%
P-glycoprotein substrate	-	0.7981	79.81%
CYP3A4 substrate	+	0.5244	52.44%
CYP2C9 substrate	-	0.5894	58.94%
CYP2D6 substrate	-	0.7788	77.88%
CYP3A4 inhibition	-	0.7696	76.96%
CYP2C9 inhibition	+	0.7745	77.45%
CYP2C19 inhibition	+	0.9187	91.87%
CYP2D6 inhibition	-	0.6910	69.10%
CYP1A2 inhibition	+	0.7982	79.82%
CYP2C8 inhibition	+	0.7845	78.45%
CYP inhibitory promiscuity	+	0.8717	87.17%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.7249	72.49%
Carcinogenicity (trinary)	Non-required	0.7202	72.02%
Eye corrosion	-	0.9913	99.13%
Eye irritation	+	0.5820	58.20%
Skin irritation	-	0.8239	82.39%
Skin corrosion	-	0.9732	97.32%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4290	42.90%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6723	67.23%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.5324	53.24%
Acute Oral Toxicity (c)	III	0.7103	71.03%
Estrogen receptor binding	+	0.9479	94.79%
Androgen receptor binding	+	0.7457	74.57%
Thyroid receptor binding	+	0.6544	65.44%
Glucocorticoid receptor binding	+	0.8907	89.07%
Aromatase binding	+	0.6649	66.49%
PPAR gamma	+	0.8498	84.98%
Honey bee toxicity	-	0.9003	90.03%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	30900 nM; 57000 nM	IC50; IC50	PMID: 19632832; PMID: 24047800

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.05%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.92%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.55%	99.17%
CHEMBL3194	P02766	Transthyretin	90.72%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.53%	97.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.94%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.49%	93.99%
CHEMBL2581	P07339	Cathepsin D	85.98%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.25%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.72%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.64%	93.10%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.15%	91.71%
CHEMBL3401	O75469	Pregnane X receptor	83.72%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.35%	95.56%
CHEMBL2535	P11166	Glucose transporter	83.14%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.36%	96.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.16%	85.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.09%	95.50%

Plants that contains it

• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis

Cross-Links

• PubChem: 9840805
• NPASS: NPC27643
• ChEMBL: CHEMBL141207
• LOTUS: LTS0183214
• wikiData: Q27286010