Licoflavone C

Details

• Internal ID: 13910f6c-7616-4310-ba37-6d4c24ef61dd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C=C(O2)C3=CC=C(C=C3)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C=C(O2)C3=CC=C(C=C3)O)C
• InChI: InChI=1S/C20H18O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3
• InChI Key: MEHHCBRCXIDGKZ-UHFFFAOYSA-N
• Popularity: 26 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.11542367 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 8-Prenylapigenin
• 72357-31-4
• 4',5,7-Trihydroxy-8-prenylflavone
• UNII-0DQ85982ZY
• 0DQ85982ZY
• CHEMBL371562
• DTXSID90904164
• 5,7,4'-Trihydroxy-8-prenylflavone
• 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• LicoflavoneC
• D0X7SR
• MEGxp0_002023
• SCHEMBL1231403
• ACon1_001079
• DTXCID401332048
• HY-N4183
• BDBM50240972
• LMPK12110422
• AKOS027326549
• NCGC00169697-01
• MS-25141
• CS-0032375
• E80589
• BRD-K74687851-001-01-8
• Q27236649
• 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.8780	87.80%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	+	0.5695	56.95%
OATP1B1 inhibitior	+	0.8625	86.25%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8212	82.12%
P-glycoprotein inhibitior	-	0.5067	50.67%
P-glycoprotein substrate	-	0.7763	77.63%
CYP3A4 substrate	+	0.5215	52.15%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	+	0.5630	56.30%
CYP2C9 inhibition	+	0.9394	93.94%
CYP2C19 inhibition	+	0.9320	93.20%
CYP2D6 inhibition	-	0.7264	72.64%
CYP1A2 inhibition	+	0.9115	91.15%
CYP2C8 inhibition	+	0.5580	55.80%
CYP inhibitory promiscuity	+	0.9498	94.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.6342	63.42%
Skin irritation	-	0.7159	71.59%
Skin corrosion	-	0.9161	91.61%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5858	58.58%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7133	71.33%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7040	70.40%
Acute Oral Toxicity (c)	III	0.6307	63.07%
Estrogen receptor binding	+	0.9388	93.88%
Androgen receptor binding	+	0.9103	91.03%
Thyroid receptor binding	+	0.6958	69.58%
Glucocorticoid receptor binding	+	0.9009	90.09%
Aromatase binding	+	0.8280	82.80%
PPAR gamma	+	0.9483	94.83%
Honey bee toxicity	-	0.8111	81.11%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9944	99.44%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL242	Q92731	Estrogen receptor beta	3.5 nM	EC50	via Super-PRED
CHEMBL288	Q08499	Phosphodiesterase 4D	630 nM	IC50	via Super-PRED
CHEMBL1827	O76074	Phosphodiesterase 5A	1290 nM	IC50	PMID: 18778098

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.19%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.40%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.30%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	94.67%	94.73%
CHEMBL3038469	P24941	CDK2/Cyclin A	92.51%	91.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.81%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.08%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.28%	91.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.07%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.88%	94.00%
CHEMBL308	P06493	Cyclin-dependent kinase 1	88.56%	91.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.30%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.30%	99.15%
CHEMBL3194	P02766	Transthyretin	85.71%	90.71%
CHEMBL301	P24941	Cyclin-dependent kinase 2	85.25%	91.23%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.69%	97.28%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.58%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.81%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.93%	86.92%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.42%	96.95%

Plants that contains it

• Artocarpus altilis
• Artocarpus heterophyllus
• Dorstenia barteri
• Ficus conraui
• Genista ephedroides
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Maclura cochinchinensis

Cross-Links

• PubChem: 10246505
• NPASS: NPC220062
• ChEMBL: CHEMBL371562
• LOTUS: LTS0122651
• wikiData: Q27236649