(3S,3aR,4aR,8aR,9aR)-4a-hydroxy-3,8a-dimethyl-5-methylidene-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: bbf05ae2-fdda-4313-a619-bcd2bbb6e3b6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aR,4aR,8aR,9aR)-4a-hydroxy-3,8a-dimethyl-5-methylidene-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CC3(C(=C)CCCC3(CC2OC1=O)C)O
• SMILES (Isomeric): C[C@H]1[C@H]2C[C@]3(C(=C)CCC[C@@]3(C[C@H]2OC1=O)C)O
• InChI: InChI=1S/C15H22O3/c1-9-5-4-6-14(3)8-12-11(7-15(9,14)17)10(2)13(16)18-12/h10-12,17H,1,4-8H2,2-3H3/t10-,11+,12+,14+,15+/m0/s1
• InChI Key: BQRXDZGXKGXLFH-PGKPSXLWSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.7693	76.93%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7267	72.67%
OATP2B1 inhibitior	-	0.8496	84.96%
OATP1B1 inhibitior	+	0.9079	90.79%
OATP1B3 inhibitior	+	0.8950	89.50%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6151	61.51%
BSEP inhibitior	-	0.8741	87.41%
P-glycoprotein inhibitior	-	0.9341	93.41%
P-glycoprotein substrate	-	0.8988	89.88%
CYP3A4 substrate	+	0.5722	57.22%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8639	86.39%
CYP3A4 inhibition	+	0.5580	55.80%
CYP2C9 inhibition	-	0.9229	92.29%
CYP2C19 inhibition	-	0.7078	70.78%
CYP2D6 inhibition	-	0.9466	94.66%
CYP1A2 inhibition	-	0.6908	69.08%
CYP2C8 inhibition	-	0.9108	91.08%
CYP inhibitory promiscuity	-	0.9026	90.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5185	51.85%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8624	86.24%
Skin irritation	+	0.5864	58.64%
Skin corrosion	-	0.9106	91.06%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5760	57.60%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.7357	73.57%
skin sensitisation	-	0.6567	65.67%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5611	56.11%
Acute Oral Toxicity (c)	III	0.5115	51.15%
Estrogen receptor binding	+	0.6993	69.93%
Androgen receptor binding	+	0.5325	53.25%
Thyroid receptor binding	+	0.6020	60.20%
Glucocorticoid receptor binding	+	0.8044	80.44%
Aromatase binding	+	0.5527	55.27%
PPAR gamma	-	0.6183	61.83%
Honey bee toxicity	-	0.8501	85.01%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.62%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.43%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.40%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.26%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.35%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.91%	94.75%
CHEMBL299	P17252	Protein kinase C alpha	83.67%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.98%	96.09%

Plants that contains it

• Artemisia lancea
• Carpesium abrotanoides
• Carpesium macrocephalum

Cross-Links

• PubChem: 13992469
• LOTUS: LTS0186444
• wikiData: Q104401931