(3S,3aS,5aR,9aS,9bS)-3,5a-dimethyl-9-methylidene-3,3a,4,5,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2,6-dione

Details

• Internal ID: 00c3e591-cdd7-489b-aa23-3c955567d209
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aR,9aS,9bS)-3,5a-dimethyl-9-methylidene-3,3a,4,5,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1C2CCC3(C(C2OC1=O)C(=C)CCC3=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]3([C@@H]([C@H]2OC1=O)C(=C)CCC3=O)C
• InChI: InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-10,12-13H,1,4-7H2,2-3H3/t9-,10-,12+,13-,15-/m0/s1
• InChI Key: QENSSLHXJBTFPU-KKQCIPQASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.50
• 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	+	0.9962	99.62%
Caco-2	+	0.7752	77.52%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6804	68.04%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9034	90.34%
OATP1B3 inhibitior	+	0.8860	88.60%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	-	0.9416	94.16%
P-glycoprotein inhibitior	-	0.8800	88.00%
P-glycoprotein substrate	-	0.9084	90.84%
CYP3A4 substrate	+	0.5925	59.25%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8513	85.13%
CYP3A4 inhibition	-	0.5551	55.51%
CYP2C9 inhibition	-	0.9479	94.79%
CYP2C19 inhibition	-	0.6827	68.27%
CYP2D6 inhibition	-	0.9484	94.84%
CYP1A2 inhibition	+	0.6299	62.99%
CYP2C8 inhibition	-	0.8854	88.54%
CYP inhibitory promiscuity	-	0.8554	85.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5374	53.74%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.6083	60.83%
Skin irritation	+	0.5336	53.36%
Skin corrosion	-	0.8607	86.07%
Ames mutagenesis	-	0.7537	75.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6870	68.70%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.7200	72.00%
skin sensitisation	-	0.5761	57.61%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5213	52.13%
Acute Oral Toxicity (c)	III	0.7531	75.31%
Estrogen receptor binding	-	0.5858	58.58%
Androgen receptor binding	+	0.5759	57.59%
Thyroid receptor binding	+	0.5334	53.34%
Glucocorticoid receptor binding	+	0.5557	55.57%
Aromatase binding	-	0.7919	79.19%
PPAR gamma	-	0.7094	70.94%
Honey bee toxicity	-	0.7698	76.98%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	93.14%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.43%	97.25%
CHEMBL1978	P11511	Cytochrome P450 19A1	89.81%	91.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.21%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.99%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.30%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.14%	93.04%
CHEMBL1937	Q92769	Histone deacetylase 2	83.57%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.48%	97.09%
CHEMBL2581	P07339	Cathepsin D	80.72%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.57%	96.38%

Plants that contains it

• Artemisia cana

Cross-Links

• PubChem: 10562519
• LOTUS: LTS0221866
• wikiData: Q105219316