(2R)-2-[[(1S,4aR,6S,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-3-methyl-2H-furan-5-one

Details

• Internal ID: 72e7e669-8637-4491-8a50-85aace145681
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2R)-2-[[(1S,4aR,6S,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-3-methyl-2H-furan-5-one
• InChI: InChI=1S/C20H30O3/c1-12-6-7-16-19(3,4)17(21)8-9-20(16,5)14(12)11-15-13(2)10-18(22)23-15/h10,14-17,21H,1,6-9,11H2,2-5H3/t14-,15+,16-,17-,20+/m0/s1
• InChI Key: KYUNUNFBPZMSAD-YPLULLRNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	+	0.7943	79.43%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7387	73.87%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.8647	86.47%
OATP1B3 inhibitior	+	0.8233	82.33%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.5317	53.17%
P-glycoprotein inhibitior	-	0.7033	70.33%
P-glycoprotein substrate	-	0.8589	85.89%
CYP3A4 substrate	+	0.6780	67.80%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	-	0.8987	89.87%
CYP3A4 inhibition	+	0.6412	64.12%
CYP2C9 inhibition	-	0.8180	81.80%
CYP2C19 inhibition	-	0.6612	66.12%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.8260	82.60%
CYP2C8 inhibition	-	0.8314	83.14%
CYP inhibitory promiscuity	-	0.7851	78.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6324	63.24%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8636	86.36%
Skin irritation	+	0.5900	59.00%
Skin corrosion	-	0.9274	92.74%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7632	76.32%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5916	59.16%
skin sensitisation	-	0.6249	62.49%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7959	79.59%
Acute Oral Toxicity (c)	III	0.6251	62.51%
Estrogen receptor binding	+	0.7426	74.26%
Androgen receptor binding	+	0.5520	55.20%
Thyroid receptor binding	+	0.7179	71.79%
Glucocorticoid receptor binding	+	0.8590	85.90%
Aromatase binding	+	0.6087	60.87%
PPAR gamma	+	0.6513	65.13%
Honey bee toxicity	-	0.8744	87.44%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	93.55%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.78%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.98%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.89%	97.25%
CHEMBL1871	P10275	Androgen Receptor	88.81%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.31%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.77%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.03%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.66%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.59%	89.00%

Plants that contains it

• Rauvolfia tetraphylla

Cross-Links

• PubChem: 162881984
• LOTUS: LTS0244907
• wikiData: Q105147950