(2S)-3-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

Details

• Internal ID: cc439ae2-a0a6-4efc-a511-92d24bb2deae
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2S)-3-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
• InChI: InChI=1S/C20H30O3/c1-13-6-5-7-16-19(13,3)10-8-14(2)20(16,4)11-9-15-12-17(21)23-18(15)22/h6,12,14,16,18,22H,5,7-11H2,1-4H3/t14-,16+,18+,19+,20+/m1/s1
• InChI Key: LVSCWEDTMWAASP-KXAOQFNBSA-N
• Popularity: 7 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: 4.50
• Atomic LogP (AlogP): 4.37
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• SCHEMBL16363005
• BDBM50353742

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.6199	61.99%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5597	55.97%
OATP2B1 inhibitior	-	0.8647	86.47%
OATP1B1 inhibitior	+	0.8817	88.17%
OATP1B3 inhibitior	+	0.8684	86.84%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7725	77.25%
P-glycoprotein inhibitior	-	0.6121	61.21%
P-glycoprotein substrate	-	0.8296	82.96%
CYP3A4 substrate	+	0.6236	62.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8948	89.48%
CYP3A4 inhibition	-	0.6567	65.67%
CYP2C9 inhibition	-	0.6941	69.41%
CYP2C19 inhibition	-	0.6240	62.40%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.5282	52.82%
CYP2C8 inhibition	-	0.7572	75.72%
CYP inhibitory promiscuity	-	0.7544	75.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5419	54.19%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9451	94.51%
Skin irritation	+	0.5295	52.95%
Skin corrosion	-	0.9348	93.48%
Ames mutagenesis	-	0.6966	69.66%
Human Ether-a-go-go-Related Gene inhibition	+	0.7797	77.97%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.5301	53.01%
skin sensitisation	-	0.6610	66.10%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6300	63.00%
Acute Oral Toxicity (c)	III	0.5112	51.12%
Estrogen receptor binding	+	0.7765	77.65%
Androgen receptor binding	+	0.5819	58.19%
Thyroid receptor binding	+	0.6319	63.19%
Glucocorticoid receptor binding	+	0.7142	71.42%
Aromatase binding	+	0.5431	54.31%
PPAR gamma	+	0.5735	57.35%
Honey bee toxicity	-	0.8416	84.16%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL402	P04035	HMG-CoA reductase	30200 nM	IC50	PMID: 18298075

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.95%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.58%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.74%	91.11%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	90.06%	86.00%
CHEMBL2581	P07339	Cathepsin D	89.08%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.61%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.03%	95.56%
CHEMBL1871	P10275	Androgen Receptor	85.09%	96.43%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.52%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.86%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.13%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.11%	96.61%

Plants that contains it

• Callicarpa americana

Cross-Links

• PubChem: 44224156
• NPASS: NPC42586
• ChEMBL: CHEMBL486985
• LOTUS: LTS0103268
• wikiData: Q105158025