(4aR,5S)-3,4a,5-trimethyl-5,6-dihydro-4H-benzo[f][1]benzofuran-7,9-dione

Details

• Internal ID: f95ca975-d8ae-4d18-8eb3-af2c2cde6c56
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4aR,5S)-3,4a,5-trimethyl-5,6-dihydro-4H-benzo[f][1]benzofuran-7,9-dione
• SMILES (Canonical): CC1CC(=O)C=C2C1(CC3=C(C2=O)OC=C3C)C
• SMILES (Isomeric): C[C@H]1CC(=O)C=C2[C@@]1(CC3=C(C2=O)OC=C3C)C
• InChI: InChI=1S/C15H16O3/c1-8-7-18-14-11(8)6-15(3)9(2)4-10(16)5-12(15)13(14)17/h5,7,9H,4,6H2,1-3H3/t9-,15+/m0/s1
• InChI Key: RQQZTSDDGPRUER-BJOHPYRUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 47.30 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7749	77.49%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7214	72.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9087	90.87%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7390	73.90%
P-glycoprotein inhibitior	-	0.9311	93.11%
P-glycoprotein substrate	-	0.8219	82.19%
CYP3A4 substrate	+	0.5650	56.50%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.8529	85.29%
CYP3A4 inhibition	-	0.5173	51.73%
CYP2C9 inhibition	-	0.6088	60.88%
CYP2C19 inhibition	-	0.5257	52.57%
CYP2D6 inhibition	-	0.7989	79.89%
CYP1A2 inhibition	+	0.6659	66.59%
CYP2C8 inhibition	-	0.8099	80.99%
CYP inhibitory promiscuity	+	0.7125	71.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4292	42.92%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9280	92.80%
Skin irritation	-	0.6203	62.03%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4380	43.80%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.5533	55.33%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4877	48.77%
Acute Oral Toxicity (c)	III	0.5528	55.28%
Estrogen receptor binding	-	0.7279	72.79%
Androgen receptor binding	+	0.6301	63.01%
Thyroid receptor binding	-	0.6509	65.09%
Glucocorticoid receptor binding	-	0.5747	57.47%
Aromatase binding	-	0.5485	54.85%
PPAR gamma	+	0.5221	52.21%
Honey bee toxicity	-	0.8587	85.87%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9951	99.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.15%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.09%	91.11%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	90.54%	86.00%
CHEMBL2581	P07339	Cathepsin D	90.38%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.23%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.40%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.36%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.87%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.78%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.65%	100.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.49%	85.30%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.15%	96.77%

Plants that contains it

• Euryops chrysanthemoides

Cross-Links

• PubChem: 163105855
• LOTUS: LTS0173428
• wikiData: Q105243521