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

Details

• Internal ID: ed7400c6-d698-442f-a4a2-aea7050be7df
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (3,4a,5-trimethyl-5,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-6-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC=C2CC3=C(CC2(C1C)C)C(=CO3)C
• SMILES (Isomeric): CC=C(C)C(=O)OC1CC=C2CC3=C(CC2(C1C)C)C(=CO3)C
• InChI: InChI=1S/C20H26O3/c1-6-12(2)19(21)23-17-8-7-15-9-18-16(13(3)11-22-18)10-20(15,5)14(17)4/h6-7,11,14,17H,8-10H2,1-5H3
• InChI Key: LDVYGJZVOMMAOC-UHFFFAOYSA-N
• Popularity: 0 references 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): 39.40 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.54
• 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	+	0.8781	87.81%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6616	66.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8970	89.70%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8173	81.73%
P-glycoprotein inhibitior	-	0.6640	66.40%
P-glycoprotein substrate	-	0.7810	78.10%
CYP3A4 substrate	+	0.6422	64.22%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.5257	52.57%
CYP2C9 inhibition	-	0.7069	70.69%
CYP2C19 inhibition	+	0.7280	72.80%
CYP2D6 inhibition	-	0.9252	92.52%
CYP1A2 inhibition	+	0.5456	54.56%
CYP2C8 inhibition	-	0.6068	60.68%
CYP inhibitory promiscuity	+	0.6396	63.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4803	48.03%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9652	96.52%
Skin irritation	-	0.6492	64.92%
Skin corrosion	-	0.9675	96.75%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8973	89.73%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.6537	65.37%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5853	58.53%
Acute Oral Toxicity (c)	III	0.5702	57.02%
Estrogen receptor binding	+	0.6903	69.03%
Androgen receptor binding	+	0.5476	54.76%
Thyroid receptor binding	+	0.6282	62.82%
Glucocorticoid receptor binding	+	0.6174	61.74%
Aromatase binding	+	0.6698	66.98%
PPAR gamma	+	0.7756	77.56%
Honey bee toxicity	-	0.7174	71.74%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	96.50%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.77%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.53%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	85.85%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.56%	96.09%
CHEMBL2581	P07339	Cathepsin D	84.58%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.54%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.33%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.90%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.90%	99.23%
CHEMBL1859	O95180	Voltage-gated T-type calcium channel alpha-1H subunit	80.72%	98.57%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.64%	93.56%

Plants that contains it

• Senecio flavus

Cross-Links

• PubChem: 162992383
• LOTUS: LTS0273216
• wikiData: Q105150410