(3S,3aR,4aR,8aS,9aR)-3,8a-dimethyl-5-methylidene-3,3a,4,4a,9,9a-hexahydrobenzo[f][1]benzofuran-2,6-dione

Details

• Internal ID: 84d0292a-006d-4838-99d8-4e25a9b6bab2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aR,4aR,8aS,9aR)-3,8a-dimethyl-5-methylidene-3,3a,4,4a,9,9a-hexahydrobenzo[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/h4-5,8,10-11,13H,2,6-7H2,1,3H3/t8-,10+,11-,13+,15+/m0/s1
• InChI Key: PCTOUSAHXOXMBC-WGGGYHPKSA-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: 2.60
• Atomic LogP (AlogP): 2.28
• 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	+	0.9970	99.70%
Caco-2	+	0.6702	67.02%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6304	63.04%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9104	91.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8574	85.74%
P-glycoprotein inhibitior	-	0.8866	88.66%
P-glycoprotein substrate	-	0.7245	72.45%
CYP3A4 substrate	+	0.6088	60.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8965	89.65%
CYP3A4 inhibition	+	0.5069	50.69%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.7568	75.68%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.5127	51.27%
CYP2C8 inhibition	-	0.8992	89.92%
CYP inhibitory promiscuity	-	0.7212	72.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4705	47.05%
Eye corrosion	-	0.9806	98.06%
Eye irritation	-	0.8849	88.49%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8422	84.22%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	+	0.5581	55.81%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6953	69.53%
Acute Oral Toxicity (c)	III	0.6694	66.94%
Estrogen receptor binding	+	0.6420	64.20%
Androgen receptor binding	+	0.5582	55.82%
Thyroid receptor binding	-	0.7605	76.05%
Glucocorticoid receptor binding	-	0.5554	55.54%
Aromatase binding	-	0.7422	74.22%
PPAR gamma	-	0.5948	59.48%
Honey bee toxicity	-	0.7457	74.57%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	95.73%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.66%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.75%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.41%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.84%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.40%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.38%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.77%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.67%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.22%	96.09%

Plants that contains it

• Encelia virginensis

Cross-Links

• PubChem: 101324759
• LOTUS: LTS0176173
• wikiData: Q105206024