Licoagrone

Details

• Internal ID: b788c1b2-e552-4e6d-808e-b7c0a29b50db
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 2-[4,5-dihydroxy-2-[(Z)-[6-hydroxy-7-(3-methylbut-2-enyl)-3-oxo-1-benzofuran-2-ylidene]methyl]phenyl]-6-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(3-methylbut-2-enyl)-1-benzofuran-3-one
• SMILES (Canonical): CC(=CCC1=CC2=C(C=C1O)OC(C2=O)(C3=CC(=C(C=C3C=C4C(=O)C5=C(O4)C(=C(C=C5)O)CC=C(C)C)O)O)C(=O)C6=CC(=C(C=C6)O)CC=C(C)C)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C=C1O)OC(C2=O)(C3=CC(=C(C=C3/C=C\4/C(=O)C5=C(O4)C(=C(C=C5)O)CC=C(C)C)O)O)C(=O)C6=CC(=C(C=C6)O)CC=C(C)C)C
• InChI: InChI=1S/C45H42O10/c1-23(2)7-10-26-17-28(12-15-34(26)46)43(52)45(44(53)32-18-27(11-8-24(3)4)36(48)22-39(32)55-45)33-21-38(50)37(49)19-29(33)20-40-41(51)31-14-16-35(47)30(42(31)54-40)13-9-25(5)6/h7-9,12,14-22,46-50H,10-11,13H2,1-6H3/b40-20-
• InChI Key: MEJLVLSNRYLDSG-MDCVPAOJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₄₂O₁₀
• Molecular Weight: 742.80 g/mol
• Exact Mass: 742.27779753 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: 10.20
• Atomic LogP (AlogP): 8.71
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

• CHEMBL2437367
• BDBM50441636
• 2-(4,5-dihydroxy-2-{[(2Z)-6-hydroxy-7-(3-methylbut-2-en-1-yl)-3-oxo-2,3-dihydro-1-benzofuran-2-ylidene]methyl}phenyl)-6-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]carbonyl}-5-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	-	0.8561	85.61%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7898	78.98%
OATP2B1 inhibitior	+	0.7073	70.73%
OATP1B1 inhibitior	+	0.8518	85.18%
OATP1B3 inhibitior	+	0.8894	88.94%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9888	98.88%
P-glycoprotein inhibitior	+	0.8312	83.12%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6469	64.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7692	76.92%
CYP3A4 inhibition	-	0.8287	82.87%
CYP2C9 inhibition	+	0.8984	89.84%
CYP2C19 inhibition	+	0.7732	77.32%
CYP2D6 inhibition	-	0.8753	87.53%
CYP1A2 inhibition	-	0.6673	66.73%
CYP2C8 inhibition	+	0.7476	74.76%
CYP inhibitory promiscuity	+	0.7275	72.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5015	50.15%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8702	87.02%
Skin irritation	-	0.7244	72.44%
Skin corrosion	-	0.9046	90.46%
Ames mutagenesis	+	0.6746	67.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7887	78.87%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7218	72.18%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5810	58.10%
Acute Oral Toxicity (c)	III	0.5990	59.90%
Estrogen receptor binding	+	0.8375	83.75%
Androgen receptor binding	+	0.7839	78.39%
Thyroid receptor binding	+	0.5965	59.65%
Glucocorticoid receptor binding	+	0.7597	75.97%
Aromatase binding	+	0.6329	63.29%
PPAR gamma	+	0.7572	75.72%
Honey bee toxicity	-	0.7861	78.61%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
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	6000 nM	IC50	PMID: 24047800

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.78%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	99.29%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	98.27%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.77%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	95.32%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.54%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.31%	93.40%
CHEMBL4208	P20618	Proteasome component C5	91.63%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.60%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.89%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.16%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.46%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.97%	100.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	82.91%	80.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.46%	96.00%
CHEMBL3194	P02766	Transthyretin	81.76%	90.71%

Plants that contains it

• Glycyrrhiza glabra

Cross-Links

• PubChem: 5318993
• NPASS: NPC156955
• ChEMBL: CHEMBL2437367
• LOTUS: LTS0244348
• wikiData: Q105162273