(3aR,4aS,8R,8aR,9aR)-8-hydroxy-5,8a-dimethyl-3-methylidene-4,4a,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one

Details

• Internal ID: fe503799-6565-4ed8-abfd-e99e001ea0a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aS,8R,8aR,9aR)-8-hydroxy-5,8a-dimethyl-3-methylidene-4,4a,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=CCC(C2(C1CC3C(C2)OC(=O)C3=C)C)O
• SMILES (Isomeric): CC1=CC[C@H]([C@]2([C@H]1C[C@H]3[C@@H](C2)OC(=O)C3=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/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12-,13-,15-/m1/s1
• InChI Key: SGRJYGRCAPBLSW-WPLOAARJSA-N
• Popularity: 1 reference 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: 2.00
• Atomic LogP (AlogP): 2.21
• 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	+	0.9970	99.70%
Caco-2	+	0.7478	74.78%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6809	68.09%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.8998	89.98%
OATP1B3 inhibitior	+	0.9115	91.15%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9589	95.89%
P-glycoprotein inhibitior	-	0.9381	93.81%
P-glycoprotein substrate	-	0.8763	87.63%
CYP3A4 substrate	+	0.6047	60.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	+	0.5460	54.60%
CYP2C9 inhibition	-	0.9115	91.15%
CYP2C19 inhibition	-	0.7285	72.85%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	-	0.7955	79.55%
CYP2C8 inhibition	-	0.7848	78.48%
CYP inhibitory promiscuity	-	0.8676	86.76%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4997	49.97%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.8219	82.19%
Skin irritation	+	0.5277	52.77%
Skin corrosion	-	0.9159	91.59%
Ames mutagenesis	-	0.7854	78.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5457	54.57%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.8336	83.36%
skin sensitisation	-	0.6092	60.92%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.4922	49.22%
Acute Oral Toxicity (c)	III	0.5192	51.92%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5528	55.28%
Thyroid receptor binding	-	0.5669	56.69%
Glucocorticoid receptor binding	+	0.5414	54.14%
Aromatase binding	-	0.7609	76.09%
PPAR gamma	+	0.5214	52.14%
Honey bee toxicity	-	0.8095	80.95%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9966	99.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.48%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.56%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.94%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.80%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.00%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.79%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.78%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.66%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.70%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.91%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.15%	97.25%

Plants that contains it

• Cyathocline purpurea

Cross-Links

• PubChem: 163189296
• LOTUS: LTS0129533
• wikiData: Q105252553