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

Details

• Internal ID: f9cc6eb0-ab97-48ab-8462-27ecb890fee9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4S,5aS,9aR,9bS)-4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• InChI: InChI=1S/C15H20O4/c1-8-5-4-6-14(3)7-10(16)11-9(2)13(17)19-12(11)15(8,14)18/h10-12,16,18H,1-2,4-7H2,3H3/t10-,11+,12-,14-,15-/m0/s1
• InChI Key: CMVJNYSIDKGGLC-XXUMUBMXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.5744	57.44%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6942	69.42%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9040	90.40%
OATP1B3 inhibitior	+	0.8988	89.88%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5821	58.21%
BSEP inhibitior	-	0.9783	97.83%
P-glycoprotein inhibitior	-	0.9204	92.04%
P-glycoprotein substrate	-	0.8651	86.51%
CYP3A4 substrate	+	0.5711	57.11%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.7579	75.79%
CYP2C9 inhibition	-	0.9125	91.25%
CYP2C19 inhibition	-	0.7956	79.56%
CYP2D6 inhibition	-	0.9462	94.62%
CYP1A2 inhibition	-	0.5937	59.37%
CYP2C8 inhibition	-	0.9324	93.24%
CYP inhibitory promiscuity	-	0.9338	93.38%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4460	44.60%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8189	81.89%
Skin irritation	+	0.6378	63.78%
Skin corrosion	-	0.8896	88.96%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8064	80.64%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6961	69.61%
skin sensitisation	-	0.8052	80.52%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.6162	61.62%
Acute Oral Toxicity (c)	IV	0.4039	40.39%
Estrogen receptor binding	+	0.5898	58.98%
Androgen receptor binding	-	0.4941	49.41%
Thyroid receptor binding	-	0.6034	60.34%
Glucocorticoid receptor binding	+	0.7068	70.68%
Aromatase binding	-	0.5298	52.98%
PPAR gamma	-	0.5597	55.97%
Honey bee toxicity	-	0.8617	86.17%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9923	99.23%

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	97.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.78%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.88%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.13%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.55%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.99%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.66%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.50%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.70%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.40%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.19%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.14%	89.00%

Plants that contains it

• Artemisia tridentata

Cross-Links

• PubChem: 162914552
• LOTUS: LTS0020355
• wikiData: Q104965268