(9-Hydroxy-3,4a,5-trimethyl-2-oxo-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-7-yl) 2-methylbut-2-enoate

Details

• Internal ID: 4ea0f231-0946-4517-a6d5-f97c31ba9f82
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (9-hydroxy-3,4a,5-trimethyl-2-oxo-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-7-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C2(CC3=C(C(=O)OC3C(C2C1)O)C)C)C
• SMILES (Isomeric): CC=C(C)C(=O)OC1CC(C2(CC3=C(C(=O)OC3C(C2C1)O)C)C)C
• InChI: InChI=1S/C20H28O5/c1-6-10(2)18(22)24-13-7-11(3)20(5)9-14-12(4)19(23)25-17(14)16(21)15(20)8-13/h6,11,13,15-17,21H,7-9H2,1-5H3
• InChI Key: NWKFPVBPTYBOIG-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 5
• 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	+	0.9925	99.25%
Caco-2	+	0.7187	71.87%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7859	78.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	-	0.2210	22.10%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6651	66.51%
P-glycoprotein inhibitior	-	0.4887	48.87%
P-glycoprotein substrate	-	0.7804	78.04%
CYP3A4 substrate	+	0.6688	66.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8833	88.33%
CYP3A4 inhibition	-	0.5304	53.04%
CYP2C9 inhibition	-	0.8517	85.17%
CYP2C19 inhibition	-	0.8373	83.73%
CYP2D6 inhibition	-	0.9475	94.75%
CYP1A2 inhibition	-	0.6055	60.55%
CYP2C8 inhibition	-	0.7529	75.29%
CYP inhibitory promiscuity	-	0.8428	84.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5098	50.98%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9393	93.93%
Skin irritation	+	0.5457	54.57%
Skin corrosion	-	0.9356	93.56%
Ames mutagenesis	-	0.5855	58.55%
Human Ether-a-go-go-Related Gene inhibition	+	0.6698	66.98%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.5458	54.58%
skin sensitisation	-	0.8125	81.25%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5571	55.71%
Acute Oral Toxicity (c)	III	0.4535	45.35%
Estrogen receptor binding	+	0.8010	80.10%
Androgen receptor binding	+	0.5745	57.45%
Thyroid receptor binding	+	0.5747	57.47%
Glucocorticoid receptor binding	+	0.7701	77.01%
Aromatase binding	-	0.5116	51.16%
PPAR gamma	+	0.6101	61.01%
Honey bee toxicity	-	0.6608	66.08%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	97.90%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.16%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.18%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.36%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.92%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	88.58%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.88%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.13%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.46%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.57%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.22%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.33%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.03%	92.94%

Plants that contains it

• Petasites hybridus

Cross-Links

• PubChem: 162990193
• LOTUS: LTS0156709
• wikiData: Q105186651