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

Details

• Internal ID: 47fb2015-f5bf-414d-a8d2-aca824532374
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[(E)-2-[(1S,4aS,8aR)-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one
• SMILES (Canonical): CC1=CC(=O)C2C(CCCC2(C1C=CC3=CCOC3=O)C)(C)C
• SMILES (Isomeric): CC1=CC(=O)[C@@H]2[C@@]([C@H]1/C=C/C3=CCOC3=O)(CCCC2(C)C)C
• InChI: InChI=1S/C20H26O3/c1-13-12-16(21)17-19(2,3)9-5-10-20(17,4)15(13)7-6-14-8-11-23-18(14)22/h6-8,12,15,17H,5,9-11H2,1-4H3/b7-6+/t15-,17-,20+/m0/s1
• InChI Key: WFORKFWUKJWGDY-FKGFIRTRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.40 g/mol
• Exact Mass: 314.18819469 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.00
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.7243	72.43%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7682	76.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8477	84.77%
OATP1B3 inhibitior	+	0.9470	94.70%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7077	70.77%
P-glycoprotein inhibitior	-	0.5744	57.44%
P-glycoprotein substrate	-	0.7847	78.47%
CYP3A4 substrate	+	0.6131	61.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9097	90.97%
CYP3A4 inhibition	-	0.8544	85.44%
CYP2C9 inhibition	-	0.7625	76.25%
CYP2C19 inhibition	-	0.6775	67.75%
CYP2D6 inhibition	-	0.8863	88.63%
CYP1A2 inhibition	+	0.5862	58.62%
CYP2C8 inhibition	-	0.7054	70.54%
CYP inhibitory promiscuity	-	0.6781	67.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5175	51.75%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9522	95.22%
Skin irritation	-	0.5603	56.03%
Skin corrosion	-	0.8986	89.86%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6963	69.63%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.5364	53.64%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5957	59.57%
Acute Oral Toxicity (c)	III	0.6999	69.99%
Estrogen receptor binding	+	0.7899	78.99%
Androgen receptor binding	+	0.5555	55.55%
Thyroid receptor binding	+	0.7055	70.55%
Glucocorticoid receptor binding	+	0.7095	70.95%
Aromatase binding	+	0.6582	65.82%
PPAR gamma	+	0.6104	61.04%
Honey bee toxicity	-	0.8392	83.92%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9955	99.55%

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	96.81%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.94%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.47%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.87%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.95%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.60%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.41%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.05%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.82%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.99%	93.99%

Plants that contains it

• Hedychium coronarium

Cross-Links

• PubChem: 52942511
• NPASS: NPC118423
• ChEMBL: CHEMBL1288184
• LOTUS: LTS0130490
• wikiData: Q105304105