3-(2,4-Dihydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one

Details

• Internal ID: 62b57ee3-a607-40f9-8f98-b6ef66004417
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 8-prenylated isoflavanones
• IUPAC Name: 3-(2,4-dihydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC(=CCC1=CC2=C(C3=C1OC(C=C3)(C)C)OCC(C2=O)C4=C(C=C(C=C4)O)O)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C3=C1OC(C=C3)(C)C)OCC(C2=O)C4=C(C=C(C=C4)O)O)C
• InChI: InChI=1S/C25H26O5/c1-14(2)5-6-15-11-19-22(28)20(17-8-7-16(26)12-21(17)27)13-29-24(19)18-9-10-25(3,4)30-23(15)18/h5,7-12,20,26-27H,6,13H2,1-4H3
• InChI Key: DORNSNGHFGIOBF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₅
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.17802393 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.15
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9756	97.56%
Caco-2	+	0.5494	54.94%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8034	80.34%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8649	86.49%
OATP1B3 inhibitior	+	0.9321	93.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9270	92.70%
P-glycoprotein inhibitior	+	0.7005	70.05%
P-glycoprotein substrate	+	0.7533	75.33%
CYP3A4 substrate	+	0.6768	67.68%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.7681	76.81%
CYP3A4 inhibition	-	0.7626	76.26%
CYP2C9 inhibition	+	0.8186	81.86%
CYP2C19 inhibition	+	0.8758	87.58%
CYP2D6 inhibition	-	0.8100	81.00%
CYP1A2 inhibition	+	0.7784	77.84%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.8975	89.75%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7095	70.95%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.4807	48.07%
Skin irritation	-	0.7504	75.04%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3613	36.13%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7831	78.31%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7155	71.55%
Acute Oral Toxicity (c)	III	0.5984	59.84%
Estrogen receptor binding	+	0.9472	94.72%
Androgen receptor binding	+	0.8219	82.19%
Thyroid receptor binding	+	0.6634	66.34%
Glucocorticoid receptor binding	+	0.8134	81.34%
Aromatase binding	+	0.6327	63.27%
PPAR gamma	+	0.8574	85.74%
Honey bee toxicity	-	0.7890	78.90%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9913	99.13%

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	99.54%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.15%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.70%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.20%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.91%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.76%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.05%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.89%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.39%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.33%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.58%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	88.31%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.64%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.67%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	85.68%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.25%	95.89%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.09%	96.12%
CHEMBL2535	P11166	Glucose transporter	84.83%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.47%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.67%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.18%	99.15%
CHEMBL221	P23219	Cyclooxygenase-1	81.25%	90.17%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.66%	89.50%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.02%	93.40%

Plants that contains it

• Erythrina variegata

Cross-Links

• PubChem: 15390742
• LOTUS: LTS0220956
• wikiData: Q104986158