(4aS,5R,8aS,9aS)-3,5,8a-trimethyl-4a,5,9,9a-tetrahydro-4H-benzo[f][1]benzofuran-2,6-dione

Details

• Internal ID: 2126e06f-c12a-4494-8c97-c536aa9442f0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aS,5R,8aS,9aS)-3,5,8a-trimethyl-4a,5,9,9a-tetrahydro-4H-benzo[f][1]benzofuran-2,6-dione
• InChI: InChI=1S/C15H18O3/c1-8-10-6-11-9(2)12(16)4-5-15(11,3)7-13(10)18-14(8)17/h4-5,9,11,13H,6-7H2,1-3H3/t9-,11+,13+,15-/m1/s1
• InChI Key: GKLAKRKLDXLWBM-WRPZCXLFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.42
• 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	+	0.7013	70.13%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6689	66.89%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8931	89.31%
OATP1B3 inhibitior	+	0.9653	96.53%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7801	78.01%
P-glycoprotein inhibitior	-	0.8733	87.33%
P-glycoprotein substrate	-	0.8466	84.66%
CYP3A4 substrate	+	0.6201	62.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9062	90.62%
CYP3A4 inhibition	-	0.6542	65.42%
CYP2C9 inhibition	-	0.9168	91.68%
CYP2C19 inhibition	-	0.8551	85.51%
CYP2D6 inhibition	-	0.9618	96.18%
CYP1A2 inhibition	-	0.5578	55.78%
CYP2C8 inhibition	-	0.8698	86.98%
CYP inhibitory promiscuity	-	0.7298	72.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4177	41.77%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.8603	86.03%
Skin irritation	+	0.5373	53.73%
Skin corrosion	-	0.8831	88.31%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4547	45.47%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.5603	56.03%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7337	73.37%
Estrogen receptor binding	-	0.5937	59.37%
Androgen receptor binding	+	0.6251	62.51%
Thyroid receptor binding	-	0.7693	76.93%
Glucocorticoid receptor binding	-	0.6529	65.29%
Aromatase binding	-	0.8169	81.69%
PPAR gamma	-	0.5704	57.04%
Honey bee toxicity	-	0.8637	86.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7300	73.00%
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
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.89%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.87%	91.11%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	89.24%	86.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.57%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.72%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.62%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.99%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.43%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.06%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.91%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	80.61%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	80.42%	94.73%

Plants that contains it

• Lindera aggregata

Cross-Links

• PubChem: 11528884
• LOTUS: LTS0229330
• wikiData: Q105010120