5,7-Dihydroxy-3-[3-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one

Details

• Internal ID: fb1ac498-cd9e-4887-a8b6-7db18b4ab37a
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 3-prenylated isoflavanones
• IUPAC Name: 5,7-dihydroxy-3-[3-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)C2COC3=CC(=CC(=C3C2=O)O)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)C2COC3=CC(=CC(=C3C2=O)O)O)O)OC)C
• InChI: InChI=1S/C21H22O6/c1-11(2)4-5-12-6-13(7-17(24)21(12)26-3)15-10-27-18-9-14(22)8-16(23)19(18)20(15)25/h4,6-9,15,22-24H,5,10H2,1-3H3
• InChI Key: GYRNAYOOXNCAQM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14163842 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9549	95.49%
Caco-2	+	0.6361	63.61%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6668	66.68%
OATP2B1 inhibitior	-	0.7166	71.66%
OATP1B1 inhibitior	+	0.9191	91.91%
OATP1B3 inhibitior	+	0.8902	89.02%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6938	69.38%
P-glycoprotein inhibitior	-	0.6442	64.42%
P-glycoprotein substrate	-	0.7730	77.30%
CYP3A4 substrate	+	0.5657	56.57%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.7963	79.63%
CYP3A4 inhibition	-	0.6410	64.10%
CYP2C9 inhibition	+	0.8666	86.66%
CYP2C19 inhibition	+	0.8880	88.80%
CYP2D6 inhibition	+	0.5631	56.31%
CYP1A2 inhibition	+	0.8831	88.31%
CYP2C8 inhibition	-	0.5618	56.18%
CYP inhibitory promiscuity	+	0.9311	93.11%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7512	75.12%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8128	81.28%
Skin irritation	-	0.7858	78.58%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5784	57.84%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8311	83.11%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6520	65.20%
Acute Oral Toxicity (c)	III	0.6323	63.23%
Estrogen receptor binding	+	0.9244	92.44%
Androgen receptor binding	+	0.6511	65.11%
Thyroid receptor binding	+	0.5905	59.05%
Glucocorticoid receptor binding	+	0.8444	84.44%
Aromatase binding	+	0.5465	54.65%
PPAR gamma	+	0.8159	81.59%
Honey bee toxicity	-	0.8087	80.87%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9840	98.40%

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	99.62%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.76%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.50%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.60%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.15%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.71%	85.14%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	91.79%	92.68%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.17%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.60%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.58%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.03%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.00%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.37%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.18%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.64%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.95%	97.28%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.36%	92.62%
CHEMBL4208	P20618	Proteasome component C5	84.26%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.21%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.42%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.38%	93.40%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.15%	93.99%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.27%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.22%	99.15%
CHEMBL2535	P11166	Glucose transporter	80.41%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	80.29%	91.19%

Plants that contains it

• Bolusanthus speciosus

Cross-Links

• PubChem: 9864156
• LOTUS: LTS0210833
• wikiData: Q105024078