methyl 4a,7-dimethyl-4,6-dioxo-7,8-dihydro-5H-cyclopenta[f][1]benzofuran-7a-carboxylate

Details

• Internal ID: c85f4e17-c66c-4f6b-9d92-4906a475fbb8
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: methyl 4a,7-dimethyl-4,6-dioxo-7,8-dihydro-5H-cyclopenta[f][1]benzofuran-7a-carboxylate
• SMILES (Canonical): CC1C(=O)CC2(C1(CC3=C(C2=O)C=CO3)C(=O)OC)C
• SMILES (Isomeric): CC1C(=O)CC2(C1(CC3=C(C2=O)C=CO3)C(=O)OC)C
• InChI: InChI=1S/C15H16O5/c1-8-10(16)6-14(2)12(17)9-4-5-20-11(9)7-15(8,14)13(18)19-3/h4-5,8H,6-7H2,1-3H3
• InChI Key: NOAGOEKLGLFLHJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 73.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 5
• 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	+	0.9915	99.15%
Caco-2	+	0.7268	72.68%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6183	61.83%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9103	91.03%
OATP1B3 inhibitior	+	0.9626	96.26%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9466	94.66%
P-glycoprotein inhibitior	-	0.8594	85.94%
P-glycoprotein substrate	-	0.7504	75.04%
CYP3A4 substrate	+	0.5928	59.28%
CYP2C9 substrate	+	0.8111	81.11%
CYP2D6 substrate	-	0.8729	87.29%
CYP3A4 inhibition	-	0.8283	82.83%
CYP2C9 inhibition	-	0.8672	86.72%
CYP2C19 inhibition	-	0.8948	89.48%
CYP2D6 inhibition	-	0.9709	97.09%
CYP1A2 inhibition	-	0.7038	70.38%
CYP2C8 inhibition	-	0.7656	76.56%
CYP inhibitory promiscuity	-	0.9330	93.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6401	64.01%
Eye corrosion	-	0.9775	97.75%
Eye irritation	-	0.8824	88.24%
Skin irritation	-	0.7797	77.97%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8344	83.44%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.4506	45.06%
Acute Oral Toxicity (c)	III	0.3659	36.59%
Estrogen receptor binding	-	0.5157	51.57%
Androgen receptor binding	+	0.6629	66.29%
Thyroid receptor binding	-	0.6686	66.86%
Glucocorticoid receptor binding	-	0.6595	65.95%
Aromatase binding	-	0.7129	71.29%
PPAR gamma	-	0.6271	62.71%
Honey bee toxicity	-	0.8719	87.19%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9909	99.09%

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	98.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.76%	96.77%
CHEMBL4040	P28482	MAP kinase ERK2	91.61%	83.82%
CHEMBL2581	P07339	Cathepsin D	89.04%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.44%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.83%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.49%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.39%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.21%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.77%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.90%	94.00%
CHEMBL4208	P20618	Proteasome component C5	80.70%	90.00%

Plants that contains it

• Bryopteris filicina
• Fraxinus insularis
• Fraxinus uhdei

Cross-Links

• PubChem: 162918740
• LOTUS: LTS0237209
• wikiData: Q105340517