8-Prenylluteone

Details

• Internal ID: 86bfc133-98a8-42ca-bd40-cc9d42529a5a
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C(=CO2)C3=C(C=C(C=C3)O)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C(=CO2)C3=C(C=C(C=C3)O)O)CC=C(C)C)O)C
• InChI: InChI=1S/C25H26O6/c1-13(2)5-8-17-22(28)18(9-6-14(3)4)25-21(23(17)29)24(30)19(12-31-25)16-10-7-15(26)11-20(16)27/h5-7,10-12,26-29H,8-9H2,1-4H3
• InChI Key: VYELCIXMHUBNAL-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₆
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.17293854 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.30
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 125002-91-7
• 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methylbut-2-enyl)chromen-4-one
• 5,7,2',4'-Tetrahydroxy-6,8-diprenylisoflavone
• Eriotrichin B
• starbld0000829
• LMPK12050304
• AKOS032948908
• NCGC00385686-01!3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methylbut-2-enyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	-	0.5640	56.40%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7672	76.72%
OATP2B1 inhibitior	+	0.5782	57.82%
OATP1B1 inhibitior	+	0.8444	84.44%
OATP1B3 inhibitior	+	0.9021	90.21%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6640	66.40%
P-glycoprotein inhibitior	+	0.6306	63.06%
P-glycoprotein substrate	-	0.7678	76.78%
CYP3A4 substrate	+	0.5400	54.00%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.6880	68.80%
CYP2C9 inhibition	+	0.8752	87.52%
CYP2C19 inhibition	+	0.9083	90.83%
CYP2D6 inhibition	-	0.7874	78.74%
CYP1A2 inhibition	+	0.8424	84.24%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.9224	92.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7280	72.80%
Eye corrosion	-	0.9903	99.03%
Eye irritation	+	0.5781	57.81%
Skin irritation	-	0.7427	74.27%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7134	71.34%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7530	75.30%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6076	60.76%
Acute Oral Toxicity (c)	III	0.6102	61.02%
Estrogen receptor binding	+	0.9342	93.42%
Androgen receptor binding	+	0.8593	85.93%
Thyroid receptor binding	+	0.6668	66.68%
Glucocorticoid receptor binding	+	0.8255	82.55%
Aromatase binding	+	0.6520	65.20%
PPAR gamma	+	0.8898	88.98%
Honey bee toxicity	-	0.8735	87.35%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	99.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.91%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.92%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.89%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	92.20%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.72%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.01%	89.00%
CHEMBL4208	P20618	Proteasome component C5	85.55%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.81%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.27%	94.00%
CHEMBL3194	P02766	Transthyretin	81.72%	90.71%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.24%	89.34%

Plants that contains it

• Anthotroche myoporoides
• Astragalus flexus
• Erythrina burttii
• Erythrina senegalensis
• Erythrina sigmoidea
• Erythrina vogelii
• Helenium virginicum
• Heliotropium digynum
• Hypericum caprifoliatum
• Nannoglottis ravida

Cross-Links

• PubChem: 471687
• NPASS: NPC141795
• LOTUS: LTS0011062
• wikiData: Q104402829