4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-

Details

• Internal ID: d4a1b32c-2afc-4d1c-ad99-47010e167857
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 6-prenylated flavones
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)C
• InChI: InChI=1S/C20H18O6/c1-10(2)3-5-12-14(22)8-18-19(20(12)25)16(24)9-17(26-18)11-4-6-13(21)15(23)7-11/h3-4,6-9,21-23,25H,5H2,1-2H3
• InChI Key: AFJYQKPCJLMHCC-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.11033829 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-
• 6-Prenylluteolin
• SCHEMBL4836863
• CHEBI:175547
• DTXSID101128143
• BDBM50358101
• LMPK12110726
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9770	97.70%
Caco-2	-	0.5819	58.19%
Blood Brain Barrier	-	0.6379	63.79%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6318	63.18%
OATP2B1 inhibitior	-	0.5513	55.13%
OATP1B1 inhibitior	+	0.9421	94.21%
OATP1B3 inhibitior	+	0.9692	96.92%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6957	69.57%
P-glycoprotein inhibitior	-	0.5729	57.29%
P-glycoprotein substrate	-	0.8379	83.79%
CYP3A4 substrate	+	0.5259	52.59%
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	+	0.6221	62.21%
CYP inhibitory promiscuity	+	0.8530	85.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7154	71.54%
Eye corrosion	-	0.9894	98.94%
Eye irritation	+	0.6771	67.71%
Skin irritation	-	0.7129	71.29%
Skin corrosion	-	0.9008	90.08%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4819	48.19%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.7073	70.73%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8782	87.82%
Acute Oral Toxicity (c)	III	0.5604	56.04%
Estrogen receptor binding	+	0.9458	94.58%
Androgen receptor binding	+	0.8757	87.57%
Thyroid receptor binding	+	0.6137	61.37%
Glucocorticoid receptor binding	+	0.9367	93.67%
Aromatase binding	+	0.7625	76.25%
PPAR gamma	+	0.9567	95.67%
Honey bee toxicity	-	0.7949	79.49%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4282	P31749	Serine/threonine-protein kinase AKT	5400 nM	IC50	PMID: 22027102

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.44%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.89%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.64%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	94.55%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.40%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.77%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.75%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.43%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.19%	83.57%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.65%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.27%	94.00%
CHEMBL3194	P02766	Transthyretin	86.18%	90.71%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	84.82%	83.10%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	84.77%	98.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.45%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.47%	86.92%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.09%	89.34%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.37%	85.30%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.71%	91.38%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.38%	97.28%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.06%	91.71%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Hypericum perforatum
• Mitracarpus hirtus

Cross-Links

• PubChem: 14604081
• NPASS: NPC3825
• ChEMBL: CHEMBL1915459
• LOTUS: LTS0026504
• wikiData: Q104911271