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

Details

• Internal ID: dc6a1630-f995-4d93-b2e9-21a7073965f0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 3-[2-[(1R,4aR,7R,8aR)-7-methoxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• InChI: InChI=1S/C21H32O3/c1-14-6-9-18-20(2,3)11-16(23-5)12-21(18,4)17(14)8-7-15-10-19(22)24-13-15/h10,16-18H,1,6-9,11-13H2,2-5H3/t16-,17-,18-,21+/m1/s1
• InChI Key: ZOOLSWODYMPPIZ-IKVWTGGYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.50 g/mol
• Exact Mass: 332.23514488 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.67
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.6341	63.41%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7625	76.25%
OATP2B1 inhibitior	-	0.8649	86.49%
OATP1B1 inhibitior	+	0.8804	88.04%
OATP1B3 inhibitior	+	0.8618	86.18%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.4494	44.94%
P-glycoprotein substrate	-	0.6353	63.53%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9067	90.67%
CYP3A4 inhibition	-	0.5470	54.70%
CYP2C9 inhibition	-	0.7062	70.62%
CYP2C19 inhibition	+	0.5254	52.54%
CYP2D6 inhibition	-	0.9188	91.88%
CYP1A2 inhibition	-	0.6719	67.19%
CYP2C8 inhibition	+	0.5414	54.14%
CYP inhibitory promiscuity	-	0.6151	61.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5892	58.92%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.7949	79.49%
Skin irritation	-	0.7032	70.32%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6850	68.50%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5569	55.69%
skin sensitisation	-	0.6963	69.63%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6728	67.28%
Acute Oral Toxicity (c)	III	0.6721	67.21%
Estrogen receptor binding	+	0.7491	74.91%
Androgen receptor binding	+	0.6557	65.57%
Thyroid receptor binding	+	0.7197	71.97%
Glucocorticoid receptor binding	+	0.8364	83.64%
Aromatase binding	+	0.7359	73.59%
PPAR gamma	+	0.7262	72.62%
Honey bee toxicity	-	0.7351	73.51%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9957	99.57%

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	98.65%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.77%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.16%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.27%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.15%	93.40%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.03%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.76%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.34%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.87%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.76%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.51%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.04%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.32%	97.14%

Plants that contains it

• Leiocarpa semicalva

Cross-Links

• PubChem: 163046459
• LOTUS: LTS0228346
• wikiData: Q105380620