3,4-Dihydroxy-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one

Details

• Internal ID: 940e4617-f26d-4b86-9762-ad14eefd51cf
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Linear pyranocoumarins
• IUPAC Name: 3,4-dihydroxy-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• SMILES (Canonical): CC1(C(C(C2=C(O1)C=C3C(=C2OC)C=CC(=O)O3)O)O)C
• SMILES (Isomeric): CC1(C(C(C2=C(O1)C=C3C(=C2OC)C=CC(=O)O3)O)O)C
• InChI: InChI=1S/C15H16O6/c1-15(2)14(18)12(17)11-9(21-15)6-8-7(13(11)19-3)4-5-10(16)20-8/h4-6,12,14,17-18H,1-3H3
• InChI Key: WZJQHBPPISFUSP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.28 g/mol
• Exact Mass: 292.09468823 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8957	89.57%
Caco-2	+	0.7353	73.53%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7369	73.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5708	57.08%
P-glycoprotein inhibitior	-	0.7819	78.19%
P-glycoprotein substrate	-	0.8155	81.55%
CYP3A4 substrate	+	0.5456	54.56%
CYP2C9 substrate	-	0.6755	67.55%
CYP2D6 substrate	-	0.8147	81.47%
CYP3A4 inhibition	-	0.8367	83.67%
CYP2C9 inhibition	-	0.9643	96.43%
CYP2C19 inhibition	-	0.7818	78.18%
CYP2D6 inhibition	-	0.8839	88.39%
CYP1A2 inhibition	-	0.6664	66.64%
CYP2C8 inhibition	-	0.5742	57.42%
CYP inhibitory promiscuity	-	0.8562	85.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5117	51.17%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.5848	58.48%
Skin irritation	-	0.7661	76.61%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3908	39.08%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8967	89.67%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7532	75.32%
Acute Oral Toxicity (c)	III	0.6754	67.54%
Estrogen receptor binding	+	0.6679	66.79%
Androgen receptor binding	+	0.6181	61.81%
Thyroid receptor binding	+	0.5785	57.85%
Glucocorticoid receptor binding	+	0.6905	69.05%
Aromatase binding	+	0.5860	58.60%
PPAR gamma	+	0.8175	81.75%
Honey bee toxicity	-	0.8218	82.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9466	94.66%

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	98.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.68%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	95.33%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.12%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.39%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.71%	98.95%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	89.55%	94.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.13%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.20%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.62%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.86%	92.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.45%	96.09%
CHEMBL1871	P10275	Androgen Receptor	83.28%	96.43%

Plants that contains it

• Citrus × aurantium

Cross-Links

• PubChem: 163024792
• LOTUS: LTS0100780
• wikiData: Q105323249