7,2',4'-Trihydroxy-5-methoxy-8-prenylisoflavone

Details

• Internal ID: 6c49a29c-f717-4707-9349-43db54f8f8ff
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones
• IUPAC Name: 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)C(=CO2)C3=C(C=C(C=C3)O)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)C(=CO2)C3=C(C=C(C=C3)O)O)C
• InChI: InChI=1S/C21H20O6/c1-11(2)4-6-14-17(24)9-18(26-3)19-20(25)15(10-27-21(14)19)13-7-5-12(22)8-16(13)23/h4-5,7-10,22-24H,6H2,1-3H3
• InChI Key: RAGHIRZNTGDCED-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.12598835 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 7,2',4'-Trihydroxy-5-methoxy-8-prenylisoflavone
• LMPK12050298

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	+	0.7042	70.42%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7048	70.48%
OATP2B1 inhibitior	-	0.5635	56.35%
OATP1B1 inhibitior	+	0.8842	88.42%
OATP1B3 inhibitior	+	0.8466	84.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7121	71.21%
P-glycoprotein inhibitior	+	0.6119	61.19%
P-glycoprotein substrate	-	0.7116	71.16%
CYP3A4 substrate	+	0.5740	57.40%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.7552	75.52%
CYP3A4 inhibition	-	0.6395	63.95%
CYP2C9 inhibition	+	0.8833	88.33%
CYP2C19 inhibition	+	0.9477	94.77%
CYP2D6 inhibition	-	0.5417	54.17%
CYP1A2 inhibition	+	0.8808	88.08%
CYP2C8 inhibition	+	0.6472	64.72%
CYP inhibitory promiscuity	+	0.9500	95.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6792	67.92%
Eye corrosion	-	0.9881	98.81%
Eye irritation	+	0.6610	66.10%
Skin irritation	-	0.7722	77.22%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4479	44.79%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8343	83.43%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6308	63.08%
Acute Oral Toxicity (c)	III	0.6798	67.98%
Estrogen receptor binding	+	0.9295	92.95%
Androgen receptor binding	+	0.8308	83.08%
Thyroid receptor binding	+	0.6578	65.78%
Glucocorticoid receptor binding	+	0.8938	89.38%
Aromatase binding	+	0.6955	69.55%
PPAR gamma	+	0.8594	85.94%
Honey bee toxicity	-	0.7951	79.51%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9903	99.03%

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	99.26%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.88%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.33%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.71%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.31%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	88.47%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.14%	90.00%
CHEMBL3194	P02766	Transthyretin	86.36%	90.71%
CHEMBL2535	P11166	Glucose transporter	86.23%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.16%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.29%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	80.64%	90.20%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.57%	95.17%

Plants that contains it

• Lupinus luteus

Cross-Links

• PubChem: 44257317
• LOTUS: LTS0186594
• wikiData: Q105232598