(3aS,5aS,9bS)-5a,9-dimethyl-3-methylidene-4,5,8,9b-tetrahydro-3aH-benzo[g][1]benzofuran-2-one

Details

• Internal ID: 5b4db59b-45db-49d3-8228-582298fed30f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,5aS,9bS)-5a,9-dimethyl-3-methylidene-4,5,8,9b-tetrahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2C3C(CCC2(C=CC1)C)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C2[C@@H]3[C@@H](CC[C@]2(C=CC1)C)C(=C)C(=O)O3
• InChI: InChI=1S/C15H18O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h4,7,11,13H,2,5-6,8H2,1,3H3/t11-,13-,15+/m0/s1
• InChI Key: LOWUURLXSKVQTP-CORIIIEPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.30 g/mol
• Exact Mass: 230.130679813 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.16
• H-Bond Acceptor: 2
• 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	+	0.7786	77.86%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4577	45.77%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8730	87.30%
OATP1B3 inhibitior	+	0.9081	90.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.8499	84.99%
P-glycoprotein inhibitior	-	0.9133	91.33%
P-glycoprotein substrate	-	0.9067	90.67%
CYP3A4 substrate	+	0.6162	61.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8510	85.10%
CYP3A4 inhibition	-	0.6019	60.19%
CYP2C9 inhibition	-	0.9186	91.86%
CYP2C19 inhibition	+	0.5595	55.95%
CYP2D6 inhibition	-	0.9112	91.12%
CYP1A2 inhibition	+	0.8551	85.51%
CYP2C8 inhibition	-	0.8070	80.70%
CYP inhibitory promiscuity	-	0.6704	67.04%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4457	44.57%
Eye corrosion	-	0.9796	97.96%
Eye irritation	-	0.7054	70.54%
Skin irritation	+	0.5086	50.86%
Skin corrosion	-	0.9130	91.30%
Ames mutagenesis	-	0.8070	80.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4874	48.74%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	+	0.6011	60.11%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6854	68.54%
Acute Oral Toxicity (c)	III	0.6948	69.48%
Estrogen receptor binding	-	0.7278	72.78%
Androgen receptor binding	-	0.6676	66.76%
Thyroid receptor binding	-	0.5781	57.81%
Glucocorticoid receptor binding	-	0.5084	50.84%
Aromatase binding	-	0.7022	70.22%
PPAR gamma	-	0.5709	57.09%
Honey bee toxicity	-	0.8156	81.56%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9950	99.50%

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	92.30%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.06%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.58%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.16%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	86.94%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.85%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.17%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.92%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.33%	89.00%
CHEMBL3920	Q04759	Protein kinase C theta	80.36%	97.69%

Plants that contains it

• Rudbeckia subtomentosa

Cross-Links

• PubChem: 162847338
• LOTUS: LTS0040644
• wikiData: Q105154960