8-Prenylquercetin

Details

• Internal ID: 7ba39294-6b1f-4497-a64e-f0425205e5f0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-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)O)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)C
• InChI: InChI=1S/C20H18O7/c1-9(2)3-5-11-13(22)8-15(24)16-17(25)18(26)19(27-20(11)16)10-4-6-12(21)14(23)7-10/h3-4,6-8,21-24,26H,5H2,1-2H3
• InChI Key: ZHTTWVRMGWQEOH-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₇
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.10525291 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 143724-75-8
• CHEMBL193059
• 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
• 8-prenyl-quercetin
• D0W2BI
• SCHEMBL2686819
• DTXSID401123716
• BDBM50240974
• PD183371
• 2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-8-(3-methyl-but-2-enyl)-chromen-4-one
• 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9770	97.70%
Caco-2	+	0.5333	53.33%
Blood Brain Barrier	-	0.6379	63.79%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6318	63.18%
OATP2B1 inhibitior	+	0.5925	59.25%
OATP1B1 inhibitior	+	0.9196	91.96%
OATP1B3 inhibitior	+	0.9692	96.92%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6876	68.76%
P-glycoprotein inhibitior	-	0.7123	71.23%
P-glycoprotein substrate	-	0.7400	74.00%
CYP3A4 substrate	+	0.5327	53.27%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.6299	62.99%
CYP2C9 inhibition	+	0.8580	85.80%
CYP2C19 inhibition	+	0.7404	74.04%
CYP2D6 inhibition	-	0.7656	76.56%
CYP1A2 inhibition	+	0.7468	74.68%
CYP2C8 inhibition	+	0.6623	66.23%
CYP inhibitory promiscuity	+	0.8530	85.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7154	71.54%
Eye corrosion	-	0.9894	98.94%
Eye irritation	+	0.6030	60.30%
Skin irritation	-	0.7129	71.29%
Skin corrosion	-	0.9008	90.08%
Ames mutagenesis	+	0.6263	62.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5656	56.56%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.7073	70.73%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8275	82.75%
Acute Oral Toxicity (c)	III	0.5604	56.04%
Estrogen receptor binding	+	0.9068	90.68%
Androgen receptor binding	+	0.8341	83.41%
Thyroid receptor binding	+	0.5712	57.12%
Glucocorticoid receptor binding	+	0.8658	86.58%
Aromatase binding	+	0.6637	66.37%
PPAR gamma	+	0.9236	92.36%
Honey bee toxicity	-	0.8456	84.56%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1827	O76074	Phosphodiesterase 5A	700 nM; 700 nM	IC50; IC50	PMID: 18778098; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.23%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.36%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	95.48%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.01%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.24%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.72%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.23%	89.34%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.95%	99.15%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.87%	85.30%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	84.73%	98.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.26%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.26%	95.56%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.28%	96.12%

Plants that contains it

• Ophioglossum petiolatum
• Podophyllum hexandrum

Cross-Links

• PubChem: 9799499
• NPASS: NPC63187
• ChEMBL: CHEMBL193059
• LOTUS: LTS0188683
• wikiData: Q105376015