3-Hydroxy-2,2,10-trimethyl-3,4-dihydropyrano[3,2-c]chromen-5-one

Details

• Internal ID: 546db8f2-4930-4d5b-b5d9-a9e87d26f405
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: 3-hydroxy-2,2,10-trimethyl-3,4-dihydropyrano[3,2-c]chromen-5-one
• SMILES (Canonical): CC1=C2C(=CC=C1)OC(=O)C3=C2OC(C(C3)O)(C)C
• SMILES (Isomeric): CC1=C2C(=CC=C1)OC(=O)C3=C2OC(C(C3)O)(C)C
• InChI: InChI=1S/C15H16O4/c1-8-5-4-6-10-12(8)13-9(14(17)18-10)7-11(16)15(2,3)19-13/h4-6,11,16H,7H2,1-3H3
• InChI Key: OOAZOBQECSVLTJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	+	0.5836	58.36%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6262	62.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9276	92.76%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8184	81.84%
P-glycoprotein inhibitior	-	0.9212	92.12%
P-glycoprotein substrate	-	0.7941	79.41%
CYP3A4 substrate	+	0.5797	57.97%
CYP2C9 substrate	-	0.6340	63.40%
CYP2D6 substrate	-	0.7976	79.76%
CYP3A4 inhibition	-	0.9165	91.65%
CYP2C9 inhibition	-	0.9674	96.74%
CYP2C19 inhibition	-	0.9473	94.73%
CYP2D6 inhibition	-	0.9063	90.63%
CYP1A2 inhibition	-	0.6842	68.42%
CYP2C8 inhibition	-	0.7910	79.10%
CYP inhibitory promiscuity	-	0.9701	97.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5737	57.37%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.4847	48.47%
Skin irritation	-	0.6532	65.32%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5384	53.84%
Micronuclear	-	0.5082	50.82%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.7966	79.66%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5995	59.95%
Acute Oral Toxicity (c)	III	0.7065	70.65%
Estrogen receptor binding	+	0.7449	74.49%
Androgen receptor binding	+	0.5529	55.29%
Thyroid receptor binding	-	0.6722	67.22%
Glucocorticoid receptor binding	+	0.6609	66.09%
Aromatase binding	+	0.6225	62.25%
PPAR gamma	+	0.8163	81.63%
Honey bee toxicity	-	0.9004	90.04%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9365	93.65%

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	97.94%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.46%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.98%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.78%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.67%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.04%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.77%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	86.43%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.89%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.16%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.97%	93.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.66%	95.89%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.25%	96.39%

Plants that contains it

• Bothriocline fusca

Cross-Links

• PubChem: 163003535
• LOTUS: LTS0157883
• wikiData: Q105195274