(3aR,5S,8aR,9aR)-5-hydroxy-5,8a-dimethyl-3-methylidene-3a,6,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: ced48821-29aa-4ade-bf16-36cea0cc5f4a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,5S,8aR,9aR)-5-hydroxy-5,8a-dimethyl-3-methylidene-3a,6,7,8,9,9a-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC12CCCC(C1=CC3C(C2)OC(=O)C3=C)(C)O
• SMILES (Isomeric): C[C@]12CCC[C@](C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)(C)O
• InChI: InChI=1S/C15H20O3/c1-9-10-7-12-14(2,5-4-6-15(12,3)17)8-11(10)18-13(9)16/h7,10-11,17H,1,4-6,8H2,2-3H3/t10-,11-,14-,15+/m1/s1
• InChI Key: FWXQRJXNYYJTDY-FKGLVLAHSA-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: 2.10
• 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	+	0.9968	99.68%
Caco-2	+	0.7771	77.71%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7508	75.08%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.8807	88.07%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6401	64.01%
BSEP inhibitior	-	0.9785	97.85%
P-glycoprotein inhibitior	-	0.9284	92.84%
P-glycoprotein substrate	-	0.8773	87.73%
CYP3A4 substrate	+	0.5684	56.84%
CYP2C9 substrate	-	0.7872	78.72%
CYP2D6 substrate	-	0.8625	86.25%
CYP3A4 inhibition	-	0.5092	50.92%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.7134	71.34%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.6548	65.48%
CYP2C8 inhibition	-	0.8369	83.69%
CYP inhibitory promiscuity	-	0.8995	89.95%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4993	49.93%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.7322	73.22%
Skin irritation	+	0.5863	58.63%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7328	73.28%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6193	61.93%
skin sensitisation	-	0.6976	69.76%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5550	55.50%
Acute Oral Toxicity (c)	III	0.4980	49.80%
Estrogen receptor binding	+	0.5515	55.15%
Androgen receptor binding	-	0.5557	55.57%
Thyroid receptor binding	+	0.6007	60.07%
Glucocorticoid receptor binding	+	0.5671	56.71%
Aromatase binding	-	0.5546	55.46%
PPAR gamma	-	0.5630	56.30%
Honey bee toxicity	-	0.8961	89.61%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	95.94%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.60%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.66%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.98%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.51%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.98%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.86%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.76%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.48%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.63%	89.00%

Plants that contains it

• Calea szyszylowiczii
• Ursinia eckloniana

Cross-Links

• PubChem: 15161366
• LOTUS: LTS0187951
• wikiData: Q105003691