[(4R,4aR,5S,8aR)-3,4a,5-trimethyl-8-oxo-4,5,6,7,8a,9-hexahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 860af473-528c-4b63-9cfa-40a0837fe2a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4R,4aR,5S,8aR)-3,4a,5-trimethyl-8-oxo-4,5,6,7,8a,9-hexahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H26O4/c1-6-11(2)19(22)24-18-17-12(3)10-23-16(17)9-14-15(21)8-7-13(4)20(14,18)5/h6,10,13-14,18H,7-9H2,1-5H3/b11-6-/t13-,14-,18-,20+/m0/s1
• InChI Key: WXXUTDJJIXJPLZ-QXPCPCOISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 56.50 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.32
• 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	+	0.9961	99.61%
Caco-2	+	0.8758	87.58%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7420	74.20%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	+	0.8271	82.71%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5768	57.68%
P-glycoprotein inhibitior	-	0.5937	59.37%
P-glycoprotein substrate	-	0.7299	72.99%
CYP3A4 substrate	+	0.6185	61.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8906	89.06%
CYP3A4 inhibition	-	0.5898	58.98%
CYP2C9 inhibition	-	0.7607	76.07%
CYP2C19 inhibition	-	0.6490	64.90%
CYP2D6 inhibition	-	0.9459	94.59%
CYP1A2 inhibition	+	0.6546	65.46%
CYP2C8 inhibition	-	0.6145	61.45%
CYP inhibitory promiscuity	-	0.6613	66.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5817	58.17%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9613	96.13%
Skin irritation	-	0.5913	59.13%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	-	0.6518	65.18%
Human Ether-a-go-go-Related Gene inhibition	+	0.8015	80.15%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	-	0.8065	80.65%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7440	74.40%
Acute Oral Toxicity (c)	IV	0.3702	37.02%
Estrogen receptor binding	+	0.6046	60.46%
Androgen receptor binding	+	0.6390	63.90%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5560	55.60%
Aromatase binding	+	0.6084	60.84%
PPAR gamma	+	0.7705	77.05%
Honey bee toxicity	-	0.7544	75.44%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
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	98.46%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.72%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.59%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.19%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.29%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.02%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.81%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.96%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.01%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.54%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.88%	91.19%

Plants that contains it

• Ligularia macrophylla

Cross-Links

• PubChem: 23627124
• NPASS: NPC62799
• LOTUS: LTS0251268
• wikiData: Q105321944