Licoricone

Details

• Internal ID: 81f2a71a-2872-49ac-8bc2-af2bd9f48291
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 4-O-methylated isoflavonoids > 4-O-methylisoflavones
• IUPAC Name: 7-hydroxy-3-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=C(C(=C1OC)C2=COC3=C(C2=O)C=CC(=C3)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=C(C(=C1OC)C2=COC3=C(C2=O)C=CC(=C3)O)O)OC)C
• InChI: InChI=1S/C22H22O6/c1-12(2)5-7-15-18(26-3)10-17(24)20(22(15)27-4)16-11-28-19-9-13(23)6-8-14(19)21(16)25/h5-6,8-11,23-24H,7H2,1-4H3
• InChI Key: GGWMNTNDTRKETA-UHFFFAOYSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₆
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.14163842 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.40
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 51847-92-8
• UNII-T8X3270QWW
• T8X3270QWW
• 7-hydroxy-3-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one
• CHEBI:69094
• 4H-1-Benzopyran-4-one, 7-hydroxy-3-(6-hydroxy-2,4-dimethoxy-3-(3-methyl-2-butenyl)phenyl)-
• 7-hydroxy-3-(6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl)-4H-chromen-4-one
• 4H-1-BENZOPYRAN-4-ONE, 7-HYDROXY-3-(6-HYDROXY-2,4-DIMETHOXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-
• 7-hydroxy-3-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one
• CHEMBL4067137
• DTXSID20966174
• BCA84792
• HY-N3386
• LMPK12050069
• AKOS032949107
• 7-Hydroxy-3-[6-hydroxy-2,4-dimethoxy-3-(3-methyl-but-2-enyl)-phenyl]-1-benzopyran-4-one
• MS-26264
• CS-0024066
• C17765
• 2',7-Dihydroxy-4',6'-dimethoxy-3'-prenylisoflavone
• Q27137435
• 7-Hydroxy-3-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	+	0.7059	70.59%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8025	80.25%
OATP2B1 inhibitior	-	0.7148	71.48%
OATP1B1 inhibitior	+	0.8942	89.42%
OATP1B3 inhibitior	+	0.8489	84.89%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6365	63.65%
P-glycoprotein inhibitior	+	0.7873	78.73%
P-glycoprotein substrate	-	0.6146	61.46%
CYP3A4 substrate	+	0.6210	62.10%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.7552	75.52%
CYP3A4 inhibition	-	0.7744	77.44%
CYP2C9 inhibition	+	0.9095	90.95%
CYP2C19 inhibition	+	0.9477	94.77%
CYP2D6 inhibition	-	0.6328	63.28%
CYP1A2 inhibition	+	0.8370	83.70%
CYP2C8 inhibition	+	0.6846	68.46%
CYP inhibitory promiscuity	+	0.9465	94.65%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6303	63.03%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.6556	65.56%
Skin irritation	-	0.7822	78.22%
Skin corrosion	-	0.9674	96.74%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6046	60.46%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8334	83.34%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5848	58.48%
Acute Oral Toxicity (c)	III	0.7450	74.50%
Estrogen receptor binding	+	0.9041	90.41%
Androgen receptor binding	+	0.8194	81.94%
Thyroid receptor binding	+	0.5285	52.85%
Glucocorticoid receptor binding	+	0.9046	90.46%
Aromatase binding	+	0.5760	57.60%
PPAR gamma	+	0.7434	74.34%
Honey bee toxicity	-	0.7957	79.57%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9919	99.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.44%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.70%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.17%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.35%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.90%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.06%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	90.34%	94.75%
CHEMBL3194	P02766	Transthyretin	89.59%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.48%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	88.07%	94.73%
CHEMBL2535	P11166	Glucose transporter	87.70%	98.75%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.12%	96.12%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.72%	96.00%
CHEMBL4208	P20618	Proteasome component C5	84.49%	90.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.45%	97.28%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.80%	89.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.06%	99.15%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.17%	94.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.02%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.77%	85.14%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 5319013
• NPASS: NPC104555
• LOTUS: LTS0153934
• wikiData: Q27137435