(3aS,6R,6aS,9aR,9bS)-6-hydroxy-6-methyl-3,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: ad7072c7-6565-43e7-8e25-9f6457f8e4c4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6R,6aS,9aR,9bS)-6-hydroxy-6-methyl-3,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1(CCC2C(C3C1CCC3=C)OC(=O)C2=C)O
• SMILES (Isomeric): C[C@]1(CC[C@@H]2[C@@H]([C@@H]3[C@@H]1CCC3=C)OC(=O)C2=C)O
• InChI: InChI=1S/C15H20O3/c1-8-4-5-11-12(8)13-10(6-7-15(11,3)17)9(2)14(16)18-13/h10-13,17H,1-2,4-7H2,3H3/t10-,11-,12-,13-,15+/m0/s1
• InChI Key: AQIRJWUAVQVXIM-MJDBTJCESA-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: 1.80
• 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	+	0.9940	99.40%
Caco-2	+	0.5244	52.44%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6232	62.32%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8716	87.16%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.9699	96.99%
P-glycoprotein inhibitior	-	0.9279	92.79%
P-glycoprotein substrate	-	0.8654	86.54%
CYP3A4 substrate	+	0.6049	60.49%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.7937	79.37%
CYP2C9 inhibition	-	0.8637	86.37%
CYP2C19 inhibition	-	0.6550	65.50%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	+	0.6411	64.11%
CYP2C8 inhibition	-	0.7422	74.22%
CYP inhibitory promiscuity	-	0.9527	95.27%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5339	53.39%
Eye corrosion	-	0.9783	97.83%
Eye irritation	-	0.7216	72.16%
Skin irritation	+	0.5475	54.75%
Skin corrosion	-	0.8870	88.70%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6941	69.41%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.8411	84.11%
skin sensitisation	-	0.6778	67.78%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.6900	69.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7224	72.24%
Acute Oral Toxicity (c)	III	0.4632	46.32%
Estrogen receptor binding	+	0.7030	70.30%
Androgen receptor binding	+	0.6715	67.15%
Thyroid receptor binding	-	0.6143	61.43%
Glucocorticoid receptor binding	+	0.7094	70.94%
Aromatase binding	-	0.6821	68.21%
PPAR gamma	-	0.6273	62.73%
Honey bee toxicity	-	0.8416	84.16%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9814	98.14%

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	97.03%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.98%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.28%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	87.83%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.15%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.13%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.71%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.69%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.38%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.23%	95.89%
CHEMBL1871	P10275	Androgen Receptor	81.23%	96.43%

Plants that contains it

• Eremanthus erythropappus
• Magnolia virginiana

Cross-Links

• PubChem: 101967028
• LOTUS: LTS0187917
• wikiData: Q104916862