[(4S,4aR,5S)-3,4a,5-trimethyl-7-oxo-4,5,6,9-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: aa3f8edb-91c2-4af5-8c39-a850dcd77349
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aR,5S)-3,4a,5-trimethyl-7-oxo-4,5,6,9-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2=C(CC3=CC(=O)CC(C13C)C)OC=C2C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C2=C(CC3=CC(=O)C[C@@H]([C@@]13C)C)OC=C2C
• InChI: InChI=1S/C20H24O4/c1-6-11(2)19(22)24-18-17-12(3)10-23-16(17)9-14-8-15(21)7-13(4)20(14,18)5/h6,8,10,13,18H,7,9H2,1-5H3/b11-6-/t13-,18+,20+/m0/s1
• InChI Key: JEONCFNJWWERCQ-OLQHVUIGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 56.50 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 4
• 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	+	0.8870	88.70%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6839	68.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8491	84.91%
OATP1B3 inhibitior	+	0.8292	82.92%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6996	69.96%
P-glycoprotein inhibitior	-	0.5843	58.43%
P-glycoprotein substrate	-	0.6915	69.15%
CYP3A4 substrate	+	0.6455	64.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8906	89.06%
CYP3A4 inhibition	-	0.7066	70.66%
CYP2C9 inhibition	-	0.6588	65.88%
CYP2C19 inhibition	-	0.6720	67.20%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	+	0.5909	59.09%
CYP2C8 inhibition	-	0.6234	62.34%
CYP inhibitory promiscuity	+	0.5112	51.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4913	49.13%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9566	95.66%
Skin irritation	-	0.6403	64.03%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8728	87.28%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.7046	70.46%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4557	45.57%
Acute Oral Toxicity (c)	III	0.4462	44.62%
Estrogen receptor binding	+	0.5355	53.55%
Androgen receptor binding	+	0.6636	66.36%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4783	47.83%
Aromatase binding	+	0.5624	56.24%
PPAR gamma	+	0.8020	80.20%
Honey bee toxicity	-	0.7242	72.42%
Biodegradation	-	0.9500	95.00%
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	98.24%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.96%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.06%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.42%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.60%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.85%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.00%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.51%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.31%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.99%	100.00%

Plants that contains it

• Ligularia virgaurea

Cross-Links

• PubChem: 163190351
• LOTUS: LTS0026362
• wikiData: Q105126262