5,7-dihydroxy-8-[(2R)-2-hydroxy-3-methylbut-3-enyl]-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 0a1f34cb-11e5-4d79-b0d8-af35506ed04b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: 5,7-dihydroxy-8-[(2R)-2-hydroxy-3-methylbut-3-enyl]-2-(4-hydroxyphenyl)chromen-4-one
• InChI: InChI=1S/C20H18O6/c1-10(2)14(22)7-13-15(23)8-16(24)19-17(25)9-18(26-20(13)19)11-3-5-12(21)6-4-11/h3-6,8-9,14,21-24H,1,7H2,2H3/t14-/m1/s1
• InChI Key: IMRKJXQBGHPNGG-CQSZACIVSA-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: 3.50
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9898	98.98%
Caco-2	-	0.5464	54.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6331	63.31%
OATP2B1 inhibitior	+	0.5734	57.34%
OATP1B1 inhibitior	+	0.8463	84.63%
OATP1B3 inhibitior	+	0.8957	89.57%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7136	71.36%
P-glycoprotein inhibitior	-	0.6875	68.75%
P-glycoprotein substrate	-	0.6979	69.79%
CYP3A4 substrate	+	0.5497	54.97%
CYP2C9 substrate	-	0.5826	58.26%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	+	0.5568	55.68%
CYP2C9 inhibition	+	0.5729	57.29%
CYP2C19 inhibition	+	0.6616	66.16%
CYP2D6 inhibition	-	0.8611	86.11%
CYP1A2 inhibition	+	0.6402	64.02%
CYP2C8 inhibition	+	0.6026	60.26%
CYP inhibitory promiscuity	+	0.8088	80.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6701	67.01%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.7062	70.62%
Skin irritation	-	0.6931	69.31%
Skin corrosion	-	0.9108	91.08%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6612	66.12%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	-	0.6342	63.42%
skin sensitisation	-	0.6933	69.33%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6770	67.70%
Acute Oral Toxicity (c)	III	0.4167	41.67%
Estrogen receptor binding	+	0.9065	90.65%
Androgen receptor binding	+	0.8233	82.33%
Thyroid receptor binding	+	0.6605	66.05%
Glucocorticoid receptor binding	+	0.8858	88.58%
Aromatase binding	+	0.7693	76.93%
PPAR gamma	+	0.9051	90.51%
Honey bee toxicity	-	0.7672	76.72%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9862	98.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.90%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.17%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.30%	85.14%
CHEMBL242	Q92731	Estrogen receptor beta	94.95%	98.35%
CHEMBL1951	P21397	Monoamine oxidase A	94.74%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.32%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.50%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.03%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.01%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.54%	94.45%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	86.53%	85.11%
CHEMBL301	P24941	Cyclin-dependent kinase 2	85.61%	91.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.04%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.59%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.59%	95.56%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.00%	92.29%

Plants that contains it

• Genista ephedroides

Cross-Links

• PubChem: 163036003
• LOTUS: LTS0119972
• wikiData: Q105115892