3-(4-Hydroxyphenyl)-8,8-dimethylpyrano[2,3-f]chromen-4-one

Details

• Internal ID: 7996164c-97d4-48cc-994d-ab9560a2aae9
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Pyranoisoflavonoids
• IUPAC Name: 3-(4-hydroxyphenyl)-8,8-dimethylpyrano[2,3-f]chromen-4-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2OC=C(C3=O)C4=CC=C(C=C4)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC=C(C3=O)C4=CC=C(C=C4)O)C
• InChI: InChI=1S/C20H16O4/c1-20(2)10-9-14-17(24-20)8-7-15-18(22)16(11-23-19(14)15)12-3-5-13(21)6-4-12/h3-11,21H,1-2H3
• InChI Key: GDSRNXASWYVDMP-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₆O₄
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.35
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• SCHEMBL15106576

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.6756	67.56%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8398	83.98%
OATP2B1 inhibitior	-	0.5819	58.19%
OATP1B1 inhibitior	+	0.8981	89.81%
OATP1B3 inhibitior	+	0.9846	98.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8085	80.85%
P-glycoprotein inhibitior	+	0.6341	63.41%
P-glycoprotein substrate	-	0.8174	81.74%
CYP3A4 substrate	+	0.6067	60.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7991	79.91%
CYP3A4 inhibition	+	0.7056	70.56%
CYP2C9 inhibition	+	0.8285	82.85%
CYP2C19 inhibition	+	0.7901	79.01%
CYP2D6 inhibition	-	0.8919	89.19%
CYP1A2 inhibition	-	0.5781	57.81%
CYP2C8 inhibition	+	0.5963	59.63%
CYP inhibitory promiscuity	+	0.6271	62.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9813	98.13%
Carcinogenicity (trinary)	Non-required	0.5123	51.23%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.4781	47.81%
Skin irritation	-	0.6805	68.05%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5700	57.00%
Micronuclear	+	0.7159	71.59%
Hepatotoxicity	+	0.5882	58.82%
skin sensitisation	-	0.7998	79.98%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.7335	73.35%
Acute Oral Toxicity (c)	III	0.5693	56.93%
Estrogen receptor binding	+	0.9571	95.71%
Androgen receptor binding	+	0.8814	88.14%
Thyroid receptor binding	+	0.7857	78.57%
Glucocorticoid receptor binding	+	0.8481	84.81%
Aromatase binding	+	0.8156	81.56%
PPAR gamma	+	0.8916	89.16%
Honey bee toxicity	-	0.8886	88.86%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9821	98.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.15%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	97.37%	98.35%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.24%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.69%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.13%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	91.15%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.21%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.17%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.39%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.17%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.11%	99.15%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.93%	93.10%

Plants that contains it

• Bituminaria morisiana
• Erythrina bidwillii
• Erythrina variegata

Cross-Links

• PubChem: 9996115
• LOTUS: LTS0275697
• wikiData: Q105006937