8-Hydroxy-3,5,8a-trimethyl-4,4a,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: b7841572-45f4-4c60-abe6-3859f8b99c8c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 8-hydroxy-3,5,8a-trimethyl-4,4a,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=CCC(C2(C1CC3=C(C(=O)OC3C2)C)C)O
• SMILES (Isomeric): CC1=CCC(C2(C1CC3=C(C(=O)OC3C2)C)C)O
• InChI: InChI=1S/C15H20O3/c1-8-4-5-13(16)15(3)7-12-10(6-11(8)15)9(2)14(17)18-12/h4,11-13,16H,5-7H2,1-3H3
• InChI Key: USNIKHVJRCUVQY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.36
• 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	+	1.0000	100.00%
Caco-2	+	0.7352	73.52%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7128	71.28%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.9237	92.37%
OATP1B3 inhibitior	+	0.9670	96.70%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7654	76.54%
P-glycoprotein inhibitior	-	0.9254	92.54%
P-glycoprotein substrate	-	0.8720	87.20%
CYP3A4 substrate	+	0.6031	60.31%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.6043	60.43%
CYP2C9 inhibition	-	0.8913	89.13%
CYP2C19 inhibition	-	0.7813	78.13%
CYP2D6 inhibition	-	0.9570	95.70%
CYP1A2 inhibition	-	0.7971	79.71%
CYP2C8 inhibition	-	0.8897	88.97%
CYP inhibitory promiscuity	-	0.8563	85.63%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4662	46.62%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8947	89.47%
Skin irritation	+	0.5951	59.51%
Skin corrosion	-	0.9320	93.20%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6029	60.29%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.7033	70.33%
skin sensitisation	-	0.6919	69.19%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5140	51.40%
Acute Oral Toxicity (c)	III	0.5776	57.76%
Estrogen receptor binding	-	0.5344	53.44%
Androgen receptor binding	-	0.4813	48.13%
Thyroid receptor binding	-	0.6078	60.78%
Glucocorticoid receptor binding	+	0.5408	54.08%
Aromatase binding	-	0.7921	79.21%
PPAR gamma	+	0.7374	73.74%
Honey bee toxicity	-	0.8982	89.82%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9935	99.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.87%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.55%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.38%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.52%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.20%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.14%	96.09%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.88%	86.00%
CHEMBL3401	O75469	Pregnane X receptor	83.23%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.83%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.45%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.62%	97.25%

Plants that contains it

• Chloranthus serratus

Cross-Links

• PubChem: 75058505
• LOTUS: LTS0028470
• wikiData: Q105278346