[(3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 7ff348ed-66c0-4fc0-8d3a-8122d0e814df
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H24O4/c1-6-10(2)19(21)23-16-9-15-11(3)7-8-14-12(4)20(22)24-18(14)17(15)13(16)5/h6,14-18H,3-5,7-9H2,1-2H3/b10-6-/t14-,15-,16-,17-,18-/m0/s1
• InChI Key: VNDHCIXTGGYXNT-CJJKOKKRSA-N
• Popularity: 2 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): 52.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.50
• 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	+	0.9871	98.71%
Caco-2	+	0.5198	51.98%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7186	71.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8396	83.96%
OATP1B3 inhibitior	+	0.9240	92.40%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.4916	49.16%
P-glycoprotein inhibitior	-	0.5606	56.06%
P-glycoprotein substrate	-	0.7313	73.13%
CYP3A4 substrate	+	0.6161	61.61%
CYP2C9 substrate	-	0.6159	61.59%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.7884	78.84%
CYP2C9 inhibition	-	0.8872	88.72%
CYP2C19 inhibition	-	0.7648	76.48%
CYP2D6 inhibition	-	0.9154	91.54%
CYP1A2 inhibition	-	0.5250	52.50%
CYP2C8 inhibition	-	0.6629	66.29%
CYP inhibitory promiscuity	-	0.8279	82.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9368	93.68%
Carcinogenicity (trinary)	Non-required	0.6808	68.08%
Eye corrosion	-	0.8863	88.63%
Eye irritation	-	0.7442	74.42%
Skin irritation	-	0.7440	74.40%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.6028	60.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.5092	50.92%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.8553	85.53%
skin sensitisation	-	0.6299	62.99%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6984	69.84%
Acute Oral Toxicity (c)	III	0.5087	50.87%
Estrogen receptor binding	-	0.5913	59.13%
Androgen receptor binding	+	0.6220	62.20%
Thyroid receptor binding	-	0.5800	58.00%
Glucocorticoid receptor binding	+	0.7637	76.37%
Aromatase binding	-	0.5587	55.87%
PPAR gamma	-	0.5605	56.05%
Honey bee toxicity	-	0.6227	62.27%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9821	98.21%

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	93.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.74%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.17%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.63%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.56%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.92%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	85.37%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.52%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.07%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.59%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	80.59%	97.79%

Plants that contains it

• Zinnia elegans

Cross-Links

• PubChem: 163194513
• LOTUS: LTS0230018
• wikiData: Q105289529