(3aS,5aR,6S,9aS,9bS)-6-hydroxy-5a-methyl-3,9-dimethylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: e581c2a1-9598-4492-bd0e-9d58a3f1571f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,5aR,6S,9aS,9bS)-6-hydroxy-5a-methyl-3,9-dimethylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC12CCC3C(C1C(=C)CCC2O)OC(=O)C3=C
• SMILES (Isomeric): C[C@@]12CC[C@@H]3[C@@H]([C@H]1C(=C)CC[C@@H]2O)OC(=O)C3=C
• InChI: InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h10-13,16H,1-2,4-7H2,3H3/t10-,11-,12+,13-,15-/m0/s1
• InChI Key: FKBUODICGDOIGB-AIUMHDJVSA-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: 2.00
• 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	+	0.9969	99.69%
Caco-2	+	0.7221	72.21%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7048	70.48%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.8692	86.92%
OATP1B3 inhibitior	+	0.9062	90.62%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.9756	97.56%
P-glycoprotein inhibitior	-	0.9136	91.36%
P-glycoprotein substrate	-	0.9139	91.39%
CYP3A4 substrate	+	0.6403	64.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.5773	57.73%
CYP2C9 inhibition	-	0.9154	91.54%
CYP2C19 inhibition	-	0.5560	55.60%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.5962	59.62%
CYP2C8 inhibition	-	0.7806	78.06%
CYP inhibitory promiscuity	-	0.9136	91.36%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4825	48.25%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.6329	63.29%
Skin irritation	+	0.5853	58.53%
Skin corrosion	-	0.9020	90.20%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5747	57.47%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.9125	91.25%
skin sensitisation	-	0.6851	68.51%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5581	55.81%
Acute Oral Toxicity (c)	III	0.5072	50.72%
Estrogen receptor binding	+	0.6678	66.78%
Androgen receptor binding	+	0.7317	73.17%
Thyroid receptor binding	-	0.5775	57.75%
Glucocorticoid receptor binding	+	0.6830	68.30%
Aromatase binding	-	0.6645	66.45%
PPAR gamma	-	0.7087	70.87%
Honey bee toxicity	-	0.8616	86.16%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9937	99.37%

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	93.16%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.98%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.54%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.92%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.84%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.82%	97.25%
CHEMBL4530	P00488	Coagulation factor XIII	84.19%	96.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.94%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.56%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.53%	97.09%

Plants that contains it

• Rhinacanthus nasutus
• Schistostephium rotundifolium

Cross-Links

• PubChem: 163093468
• LOTUS: LTS0147447
• wikiData: Q105345819