(3R,3aS,5S,8aR,9aR)-3-hydroxy-3,5,8a-trimethyl-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 8c1a922a-78b0-48a2-bb88-facb3424c0c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aS,5S,8aR,9aR)-3-hydroxy-3,5,8a-trimethyl-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCCC2(C1=CC3C(C2)OC(=O)C3(C)O)C
• SMILES (Isomeric): C[C@H]1CCC[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)[C@]3(C)O)C
• InChI: InChI=1S/C15H22O3/c1-9-5-4-6-14(2)8-12-11(7-10(9)14)15(3,17)13(16)18-12/h7,9,11-12,17H,4-6,8H2,1-3H3/t9-,11-,12+,14+,15+/m0/s1
• InChI Key: SYAJBOVYQHMITJ-PRHQYYMVSA-N
• Popularity: 6 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: 2.70
• 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	+	0.9938	99.38%
Caco-2	+	0.8005	80.05%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5954	59.54%
OATP2B1 inhibitior	-	0.8524	85.24%
OATP1B1 inhibitior	+	0.9210	92.10%
OATP1B3 inhibitior	+	0.9697	96.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7250	72.50%
BSEP inhibitior	-	0.8796	87.96%
P-glycoprotein inhibitior	-	0.8876	88.76%
P-glycoprotein substrate	-	0.8794	87.94%
CYP3A4 substrate	+	0.5920	59.20%
CYP2C9 substrate	-	0.5791	57.91%
CYP2D6 substrate	-	0.8353	83.53%
CYP3A4 inhibition	-	0.7740	77.40%
CYP2C9 inhibition	-	0.9052	90.52%
CYP2C19 inhibition	-	0.7377	73.77%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	+	0.7046	70.46%
CYP2C8 inhibition	-	0.8837	88.37%
CYP inhibitory promiscuity	-	0.8840	88.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4179	41.79%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9043	90.43%
Skin irritation	+	0.6811	68.11%
Skin corrosion	-	0.9069	90.69%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8710	87.10%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.7871	78.71%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5298	52.98%
Acute Oral Toxicity (c)	III	0.5660	56.60%
Estrogen receptor binding	+	0.5585	55.85%
Androgen receptor binding	-	0.5454	54.54%
Thyroid receptor binding	+	0.6096	60.96%
Glucocorticoid receptor binding	+	0.7521	75.21%
Aromatase binding	-	0.6172	61.72%
PPAR gamma	-	0.6639	66.39%
Honey bee toxicity	-	0.9330	93.30%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6913	69.13%
Fish aquatic toxicity	+	0.9881	98.81%

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	94.67%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.67%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.40%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.15%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.92%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.12%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.73%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.63%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.17%	86.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.51%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.24%	95.89%

Plants that contains it

• Inula racemosa

Cross-Links

• PubChem: 46930145
• LOTUS: LTS0269702
• wikiData: Q105263438