(3aS,4aS,8aR,9aR)-3a-hydroxy-8a-methyl-3,5-dimethylidene-4a,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 5e654a81-d246-43c3-8cea-e473946ee7a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,4aS,8aR,9aR)-3a-hydroxy-8a-methyl-3,5-dimethylidene-4a,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC12CCCC(=C)C1CC3(C(C2)OC(=O)C3=C)O
• SMILES (Isomeric): C[C@]12CCCC(=C)[C@@H]1C[C@]3([C@@H](C2)OC(=O)C3=C)O
• InChI: InChI=1S/C15H20O3/c1-9-5-4-6-14(3)8-12-15(17,7-11(9)14)10(2)13(16)18-12/h11-12,17H,1-2,4-8H2,3H3/t11-,12+,14+,15-/m0/s1
• InChI Key: BSEQCEMTSHRFAO-MXYBEHONSA-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: 2.30
• 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	+	0.9972	99.72%
Caco-2	+	0.7036	70.36%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6116	61.16%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	+	0.9220	92.20%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.9570	95.70%
P-glycoprotein inhibitior	-	0.9323	93.23%
P-glycoprotein substrate	-	0.9178	91.78%
CYP3A4 substrate	+	0.5649	56.49%
CYP2C9 substrate	-	0.7887	78.87%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.7026	70.26%
CYP2C9 inhibition	-	0.9163	91.63%
CYP2C19 inhibition	-	0.6887	68.87%
CYP2D6 inhibition	-	0.9554	95.54%
CYP1A2 inhibition	-	0.5217	52.17%
CYP2C8 inhibition	-	0.9154	91.54%
CYP inhibitory promiscuity	-	0.9478	94.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4588	45.88%
Eye corrosion	-	0.9853	98.53%
Eye irritation	+	0.5707	57.07%
Skin irritation	+	0.5794	57.94%
Skin corrosion	-	0.8870	88.70%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4547	45.47%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6555	65.55%
skin sensitisation	-	0.7261	72.61%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4744	47.44%
Acute Oral Toxicity (c)	IV	0.5098	50.98%
Estrogen receptor binding	+	0.6234	62.34%
Androgen receptor binding	-	0.5654	56.54%
Thyroid receptor binding	-	0.5617	56.17%
Glucocorticoid receptor binding	+	0.7534	75.34%
Aromatase binding	+	0.6057	60.57%
PPAR gamma	-	0.5572	55.72%
Honey bee toxicity	-	0.9219	92.19%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9892	98.92%

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	94.97%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.37%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.43%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.29%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.11%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.66%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.90%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.77%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.94%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.36%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.81%	100.00%

Plants that contains it

• Cyanthillium cinereum

Cross-Links

• PubChem: 14707093
• LOTUS: LTS0235274
• wikiData: Q104945207