6-Prenylherbacetin 3,8-dimethyl ether

Details

• Internal ID: de7eddaf-401a-44f5-a3f5-67378c03ceb4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 6-prenylated flavones
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-dimethoxy-6-(3-methylbut-2-enyl)chromen-4-one
• InChI: InChI=1S/C22H22O7/c1-11(2)5-10-14-16(24)15-18(26)22(28-4)19(12-6-8-13(23)9-7-12)29-20(15)21(27-3)17(14)25/h5-9,23-25H,10H2,1-4H3
• InChI Key: WNCWVGUJEUECML-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₇
• Molecular Weight: 398.40 g/mol
• Exact Mass: 398.13655304 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.10
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 5,7,4'-Trihydroxy-3,8-dimethoxy-6-prenylflavone
• CHEBI:178242
• LMPK12113146
• 4',5,7-trihydroxy-3,8-dimethoxy-6-prenylflavone
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-dimethoxy-6-(3-methylbut-2-enyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9853	98.53%
Caco-2	+	0.5319	53.19%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5455	54.55%
OATP2B1 inhibitior	-	0.7031	70.31%
OATP1B1 inhibitior	+	0.8469	84.69%
OATP1B3 inhibitior	+	0.8673	86.73%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8769	87.69%
P-glycoprotein inhibitior	+	0.7245	72.45%
P-glycoprotein substrate	-	0.7253	72.53%
CYP3A4 substrate	+	0.5559	55.59%
CYP2C9 substrate	-	0.5929	59.29%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.6679	66.79%
CYP2C9 inhibition	+	0.8700	87.00%
CYP2C19 inhibition	+	0.9318	93.18%
CYP2D6 inhibition	+	0.5347	53.47%
CYP1A2 inhibition	+	0.7798	77.98%
CYP2C8 inhibition	+	0.7161	71.61%
CYP inhibitory promiscuity	+	0.9269	92.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6873	68.73%
Eye corrosion	-	0.9874	98.74%
Eye irritation	+	0.6800	68.00%
Skin irritation	-	0.7629	76.29%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5320	53.20%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.6052	60.52%
skin sensitisation	-	0.8260	82.60%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4511	45.11%
Acute Oral Toxicity (c)	III	0.6590	65.90%
Estrogen receptor binding	+	0.9449	94.49%
Androgen receptor binding	+	0.8230	82.30%
Thyroid receptor binding	+	0.6623	66.23%
Glucocorticoid receptor binding	+	0.8854	88.54%
Aromatase binding	+	0.7626	76.26%
PPAR gamma	+	0.8486	84.86%
Honey bee toxicity	-	0.8289	82.89%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9866	98.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.20%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.98%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.15%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.22%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.57%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	89.30%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.36%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.06%	91.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.55%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.34%	95.56%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.92%	95.64%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.13%	85.14%
CHEMBL301	P24941	Cyclin-dependent kinase 2	80.28%	91.23%

Plants that contains it

• Vellozia scoparia

Cross-Links

• PubChem: 44259962
• LOTUS: LTS0249311
• wikiData: Q105308992