[(1R,4aS,8aS)-3,4a,8,8-tetramethyl-4-[2-(5-oxo-2H-furan-3-yl)ethyl]-1,2,5,6,7,8a-hexahydronaphthalen-1-yl] acetate

Details

• Internal ID: 5b1bd9e4-5e96-41e5-8ba4-f8c1d8ab8491
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,4aS,8aS)-3,4a,8,8-tetramethyl-4-[2-(5-oxo-2H-furan-3-yl)ethyl]-1,2,5,6,7,8a-hexahydronaphthalen-1-yl] acetate
• SMILES (Canonical): CC1=C(C2(CCCC(C2C(C1)OC(=O)C)(C)C)C)CCC3=CC(=O)OC3
• SMILES (Isomeric): CC1=C([C@]2(CCCC([C@@H]2[C@@H](C1)OC(=O)C)(C)C)C)CCC3=CC(=O)OC3
• InChI: InChI=1S/C22H32O4/c1-14-11-18(26-15(2)23)20-21(3,4)9-6-10-22(20,5)17(14)8-7-16-12-19(24)25-13-16/h12,18,20H,6-11,13H2,1-5H3/t18-,20+,22-/m1/s1
• InChI Key: OPWCWNCERZLVTP-KAGYGMCKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.50 g/mol
• Exact Mass: 360.23005950 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.73
• H-Bond Acceptor: 4
• 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	+	0.9942	99.42%
Caco-2	+	0.5992	59.92%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8471	84.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8680	86.80%
OATP1B3 inhibitior	+	0.8891	88.91%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.8686	86.86%
P-glycoprotein inhibitior	+	0.6714	67.14%
P-glycoprotein substrate	-	0.6590	65.90%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9122	91.22%
CYP3A4 inhibition	-	0.6614	66.14%
CYP2C9 inhibition	-	0.7264	72.64%
CYP2C19 inhibition	-	0.7500	75.00%
CYP2D6 inhibition	-	0.9139	91.39%
CYP1A2 inhibition	-	0.8010	80.10%
CYP2C8 inhibition	+	0.5115	51.15%
CYP inhibitory promiscuity	-	0.6245	62.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6096	60.96%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.7762	77.62%
Skin irritation	-	0.5982	59.82%
Skin corrosion	-	0.9469	94.69%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3606	36.06%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6659	66.59%
skin sensitisation	-	0.7846	78.46%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5179	51.79%
Acute Oral Toxicity (c)	III	0.7504	75.04%
Estrogen receptor binding	+	0.7316	73.16%
Androgen receptor binding	+	0.6435	64.35%
Thyroid receptor binding	+	0.5472	54.72%
Glucocorticoid receptor binding	+	0.7917	79.17%
Aromatase binding	+	0.6718	67.18%
PPAR gamma	+	0.7108	71.08%
Honey bee toxicity	-	0.8115	81.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.97%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.91%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.88%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.28%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.76%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.97%	95.56%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	88.18%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.83%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.77%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.66%	100.00%
CHEMBL5028	O14672	ADAM10	81.21%	97.50%

Plants that contains it

• Vitex trifolia

Cross-Links

• PubChem: 71579299
• LOTUS: LTS0019503
• wikiData: Q105196598