5-Methoxy-2,8,8-trimethyl-9,10-dihydropyrano[2,3-h]chromen-4-one

Details

• Internal ID: c6fea9ee-40f6-442f-afd6-f97da41503ed
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Pyranochromenes
• IUPAC Name: 5-methoxy-2,8,8-trimethyl-9,10-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C=C3C(=C2O1)CCC(O3)(C)C)OC
• SMILES (Isomeric): CC1=CC(=O)C2=C(C=C3C(=C2O1)CCC(O3)(C)C)OC
• InChI: InChI=1S/C16H18O4/c1-9-7-11(17)14-13(18-4)8-12-10(15(14)19-9)5-6-16(2,3)20-12/h7-8H,5-6H2,1-4H3
• InChI Key: KGHHHYMIAJMZEF-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₄
• Molecular Weight: 274.31 g/mol
• Exact Mass: 274.12050905 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.8764	87.64%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7274	72.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9553	95.53%
OATP1B3 inhibitior	+	0.9865	98.65%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5950	59.50%
P-glycoprotein inhibitior	-	0.6774	67.74%
P-glycoprotein substrate	-	0.8945	89.45%
CYP3A4 substrate	+	0.5935	59.35%
CYP2C9 substrate	-	0.6462	64.62%
CYP2D6 substrate	-	0.7880	78.80%
CYP3A4 inhibition	-	0.6502	65.02%
CYP2C9 inhibition	-	0.8308	83.08%
CYP2C19 inhibition	-	0.6694	66.94%
CYP2D6 inhibition	-	0.7612	76.12%
CYP1A2 inhibition	+	0.6665	66.65%
CYP2C8 inhibition	-	0.7324	73.24%
CYP inhibitory promiscuity	-	0.8168	81.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6236	62.36%
Eye corrosion	-	0.9807	98.07%
Eye irritation	+	0.7571	75.71%
Skin irritation	-	0.7785	77.85%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	+	0.5146	51.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6795	67.95%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8398	83.98%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7239	72.39%
Estrogen receptor binding	+	0.6108	61.08%
Androgen receptor binding	+	0.6469	64.69%
Thyroid receptor binding	-	0.5105	51.05%
Glucocorticoid receptor binding	+	0.6089	60.89%
Aromatase binding	+	0.6165	61.65%
PPAR gamma	+	0.7274	72.74%
Honey bee toxicity	-	0.7341	73.41%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8957	89.57%

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	97.78%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.27%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.75%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.01%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.76%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.20%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.84%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.04%	85.30%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.74%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.97%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.79%	89.00%
CHEMBL2535	P11166	Glucose transporter	84.57%	98.75%
CHEMBL1937	Q92769	Histone deacetylase 2	80.84%	94.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.77%	82.38%

Plants that contains it

• Cedrelopsis grevei
• Harrisonia perforata

Cross-Links

• PubChem: 13147261
• LOTUS: LTS0047385
• wikiData: Q105140777