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

Details

• Internal ID: 7423be69-311c-44e9-a87d-8def59aa4a72
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-7-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C2(CC3=C(CC2C1)OC=C3C)C)C
• SMILES (Isomeric): CC=C(C)C(=O)OC1CC(C2(CC3=C(CC2C1)OC=C3C)C)C
• InChI: InChI=1S/C20H28O3/c1-6-12(2)19(21)23-16-7-14(4)20(5)10-17-13(3)11-22-18(17)9-15(20)8-16/h6,11,14-16H,7-10H2,1-5H3
• InChI Key: DDJITDJHDCLHOK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 39.40 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.62
• 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	+	1.0000	100.00%
Caco-2	+	0.9092	90.92%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6541	65.41%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.9234	92.34%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5231	52.31%
P-glycoprotein inhibitior	-	0.5607	56.07%
P-glycoprotein substrate	-	0.8235	82.35%
CYP3A4 substrate	+	0.6471	64.71%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.7360	73.60%
CYP2C19 inhibition	+	0.7715	77.15%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	+	0.5166	51.66%
CYP2C8 inhibition	+	0.4709	47.09%
CYP inhibitory promiscuity	+	0.6554	65.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4951	49.51%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9221	92.21%
Skin irritation	-	0.6590	65.90%
Skin corrosion	-	0.9710	97.10%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8583	85.83%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	-	0.6184	61.84%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5274	52.74%
Acute Oral Toxicity (c)	III	0.5314	53.14%
Estrogen receptor binding	+	0.6474	64.74%
Androgen receptor binding	+	0.5636	56.36%
Thyroid receptor binding	+	0.6279	62.79%
Glucocorticoid receptor binding	+	0.6113	61.13%
Aromatase binding	+	0.5543	55.43%
PPAR gamma	+	0.6868	68.68%
Honey bee toxicity	-	0.6944	69.44%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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	96.51%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.02%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.71%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.25%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.80%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	84.14%	91.19%
CHEMBL2581	P07339	Cathepsin D	82.55%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.77%	93.56%

Plants that contains it

• Petasites spurius
• Synotis alata

Cross-Links

• PubChem: 78384932
• LOTUS: LTS0203956
• wikiData: Q104976426