(2S)-3-[2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

Details

• Internal ID: 356b4735-a62b-4529-b75a-62d4806a5333
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2S)-3-[2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
• InChI: InChI=1S/C20H28O4/c1-12-14(7-6-13-10-17(22)24-18(13)23)20(4)9-5-8-19(2,3)16(20)11-15(12)21/h10,16,18,23H,5-9,11H2,1-4H3/t16-,18-,20+/m0/s1
• InChI Key: NMSOMIPQZUTEGY-XKGZKEIXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.69
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8055	80.55%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.8137	81.37%
OATP1B3 inhibitior	-	0.3103	31.03%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.5532	55.32%
BSEP inhibitior	+	0.8168	81.68%
P-glycoprotein inhibitior	-	0.6674	66.74%
P-glycoprotein substrate	-	0.7933	79.33%
CYP3A4 substrate	+	0.5938	59.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8920	89.20%
CYP3A4 inhibition	-	0.6471	64.71%
CYP2C9 inhibition	-	0.8287	82.87%
CYP2C19 inhibition	-	0.8477	84.77%
CYP2D6 inhibition	-	0.9645	96.45%
CYP1A2 inhibition	-	0.7531	75.31%
CYP2C8 inhibition	-	0.7472	74.72%
CYP inhibitory promiscuity	-	0.8641	86.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6012	60.12%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.8376	83.76%
Skin irritation	+	0.5987	59.87%
Skin corrosion	-	0.9055	90.55%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6452	64.52%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.7455	74.55%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6586	65.86%
Acute Oral Toxicity (c)	I	0.4037	40.37%
Estrogen receptor binding	+	0.6985	69.85%
Androgen receptor binding	+	0.6090	60.90%
Thyroid receptor binding	+	0.5791	57.91%
Glucocorticoid receptor binding	+	0.7745	77.45%
Aromatase binding	+	0.5495	54.95%
PPAR gamma	+	0.8650	86.50%
Honey bee toxicity	-	0.8410	84.10%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9967	99.67%

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	94.71%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.21%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.32%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.23%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.84%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.68%	86.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.26%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.47%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.83%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.70%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.70%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.18%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.04%	89.00%

Plants that contains it

• Leonurus japonicus

Cross-Links

• PubChem: 162978666
• LOTUS: LTS0142106
• wikiData: Q105181950