[(4aR,5S,7R,8aS,9R)-9-hydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-7-yl] 3-methylbut-2-enoate

Details

• Internal ID: 64902ab7-35ec-4c24-b0ea-119187078119
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4aR,5S,7R,8aS,9R)-9-hydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-7-yl] 3-methylbut-2-enoate
• InChI: InChI=1S/C20H28O4/c1-11(2)6-17(21)24-14-7-13(4)20(5)9-15-12(3)10-23-19(15)18(22)16(20)8-14/h6,10,13-14,16,18,22H,7-9H2,1-5H3/t13-,14+,16+,18+,20+/m0/s1
• InChI Key: NXNOPTGUMNFXAY-IJTAGJJNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 4
• 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	+	0.9948	99.48%
Caco-2	+	0.7474	74.74%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7744	77.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9142	91.42%
OATP1B3 inhibitior	-	0.2936	29.36%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6932	69.32%
P-glycoprotein inhibitior	-	0.6817	68.17%
P-glycoprotein substrate	-	0.7342	73.42%
CYP3A4 substrate	+	0.6419	64.19%
CYP2C9 substrate	-	0.6070	60.70%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	+	0.6195	61.95%
CYP2C9 inhibition	-	0.5793	57.93%
CYP2C19 inhibition	+	0.6298	62.98%
CYP2D6 inhibition	-	0.8810	88.10%
CYP1A2 inhibition	+	0.6562	65.62%
CYP2C8 inhibition	-	0.6072	60.72%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5468	54.68%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9663	96.63%
Skin irritation	-	0.6316	63.16%
Skin corrosion	-	0.9537	95.37%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7493	74.93%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7451	74.51%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6831	68.31%
Acute Oral Toxicity (c)	III	0.4831	48.31%
Estrogen receptor binding	+	0.6479	64.79%
Androgen receptor binding	+	0.6395	63.95%
Thyroid receptor binding	-	0.5220	52.20%
Glucocorticoid receptor binding	+	0.5909	59.09%
Aromatase binding	-	0.5130	51.30%
PPAR gamma	+	0.6481	64.81%
Honey bee toxicity	-	0.6368	63.68%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	96.25%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.92%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.21%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.60%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.46%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.94%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.67%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.80%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.27%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.83%	85.14%
CHEMBL5028	O14672	ADAM10	81.04%	97.50%

Plants that contains it

• Petasites hybridus

Cross-Links

• PubChem: 163185413
• LOTUS: LTS0088781
• wikiData: Q105187264