[(3S,3aR,8aS,9aR)-3,5-dimethyl-2-oxo-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8a-yl]methyl acetate

Details

• Internal ID: 5aa991af-5ee7-4f1b-aeac-e7128000a55d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3S,3aR,8aS,9aR)-3,5-dimethyl-2-oxo-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8a-yl]methyl acetate
• SMILES (Canonical): CC1C2CC3=C(CCCC3(CC2OC1=O)COC(=O)C)C
• SMILES (Isomeric): C[C@H]1[C@H]2CC3=C(CCC[C@@]3(C[C@H]2OC1=O)COC(=O)C)C
• InChI: InChI=1S/C17H24O4/c1-10-5-4-6-17(9-20-12(3)18)8-15-13(7-14(10)17)11(2)16(19)21-15/h11,13,15H,4-9H2,1-3H3/t11-,13+,15+,17+/m0/s1
• InChI Key: NMFHHVBUJTUWEJ-BYMSMCERSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.40 g/mol
• Exact Mass: 292.16745924 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.8573	85.73%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8289	82.89%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8556	85.56%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.6254	62.54%
P-glycoprotein inhibitior	-	0.7296	72.96%
P-glycoprotein substrate	-	0.8026	80.26%
CYP3A4 substrate	+	0.6199	61.99%
CYP2C9 substrate	-	0.8156	81.56%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.6363	63.63%
CYP2C9 inhibition	-	0.8273	82.73%
CYP2C19 inhibition	-	0.8571	85.71%
CYP2D6 inhibition	-	0.9251	92.51%
CYP1A2 inhibition	-	0.7601	76.01%
CYP2C8 inhibition	-	0.8379	83.79%
CYP inhibitory promiscuity	-	0.6661	66.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5920	59.20%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.7960	79.60%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9444	94.44%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5569	55.69%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6458	64.58%
skin sensitisation	-	0.8721	87.21%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6938	69.38%
Acute Oral Toxicity (c)	III	0.7997	79.97%
Estrogen receptor binding	+	0.5485	54.85%
Androgen receptor binding	-	0.5188	51.88%
Thyroid receptor binding	-	0.5861	58.61%
Glucocorticoid receptor binding	+	0.5856	58.56%
Aromatase binding	-	0.7887	78.87%
PPAR gamma	-	0.5144	51.44%
Honey bee toxicity	-	0.8031	80.31%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	97.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.62%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.00%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.09%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	87.67%	98.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.08%	94.45%
CHEMBL2581	P07339	Cathepsin D	84.33%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.66%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.73%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.50%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.71%	86.33%

Plants that contains it

• Eriocephalus africanus

Cross-Links

• PubChem: 13895689
• LOTUS: LTS0207448
• wikiData: Q105181741