[(3aR,6aR,9aR,9bS)-3,9-dimethylidene-2-oxo-4,6a,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl (Z)-2-methylbut-2-enoate

Details

• Internal ID: 0de32a42-0f97-4d3a-bafe-1e8345dff684
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,6aR,9aR,9bS)-3,9-dimethylidene-2-oxo-4,6a,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6-yl]methyl (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H24O4/c1-5-11(2)19(21)23-10-14-7-9-15-13(4)20(22)24-18(15)17-12(3)6-8-16(14)17/h5,7,15-18H,3-4,6,8-10H2,1-2H3/b11-5-/t15-,16+,17+,18+/m1/s1
• InChI Key: KZXDGURWGUXFAF-UKOPGGKHSA-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): 3.51
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9852	98.52%
Caco-2	+	0.5437	54.37%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7262	72.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8642	86.42%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4702	47.02%
P-glycoprotein inhibitior	-	0.6936	69.36%
P-glycoprotein substrate	-	0.7623	76.23%
CYP3A4 substrate	+	0.6272	62.72%
CYP2C9 substrate	-	0.6159	61.59%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.7369	73.69%
CYP2C9 inhibition	-	0.7220	72.20%
CYP2C19 inhibition	-	0.6708	67.08%
CYP2D6 inhibition	-	0.8493	84.93%
CYP1A2 inhibition	+	0.6651	66.51%
CYP2C8 inhibition	-	0.5851	58.51%
CYP inhibitory promiscuity	-	0.6020	60.20%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.6960	69.60%
Eye corrosion	-	0.9331	93.31%
Eye irritation	-	0.8764	87.64%
Skin irritation	-	0.6625	66.25%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6556	65.56%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.6237	62.37%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.8133	81.33%
Acute Oral Toxicity (c)	III	0.6203	62.03%
Estrogen receptor binding	-	0.5402	54.02%
Androgen receptor binding	+	0.6382	63.82%
Thyroid receptor binding	-	0.5886	58.86%
Glucocorticoid receptor binding	+	0.7762	77.62%
Aromatase binding	-	0.5723	57.23%
PPAR gamma	-	0.6785	67.85%
Honey bee toxicity	-	0.7674	76.74%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9917	99.17%

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	96.95%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.92%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.42%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.97%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.89%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.20%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.87%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.15%	97.25%
CHEMBL2581	P07339	Cathepsin D	84.49%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.04%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.71%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.00%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.39%	95.89%

Plants that contains it

• Zinnia elegans

Cross-Links

• PubChem: 163075011
• LOTUS: LTS0109218
• wikiData: Q105148490