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

Details

• Internal ID: 36396dde-b875-4957-86c7-79314d9308fb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,5R,6aR,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-5-yl] 3-methylbut-2-enoate
• InChI: InChI=1S/C20H24O4/c1-10(2)8-17(21)23-16-9-15-13(5)20(22)24-19(15)18-11(3)6-7-14(18)12(16)4/h8,14-16,18-19H,3-7,9H2,1-2H3/t14-,15+,16+,18-,19-/m0/s1
• InChI Key: DDFUOJNBHWSVLD-CFRSGVNKSA-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: 3.50
• 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	+	0.9869	98.69%
Caco-2	+	0.6558	65.58%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7272	72.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8816	88.16%
OATP1B3 inhibitior	+	0.8964	89.64%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5113	51.13%
P-glycoprotein inhibitior	-	0.6422	64.22%
P-glycoprotein substrate	-	0.6373	63.73%
CYP3A4 substrate	+	0.6171	61.71%
CYP2C9 substrate	-	0.6183	61.83%
CYP2D6 substrate	-	0.9104	91.04%
CYP3A4 inhibition	-	0.8614	86.14%
CYP2C9 inhibition	-	0.8474	84.74%
CYP2C19 inhibition	-	0.7367	73.67%
CYP2D6 inhibition	-	0.8967	89.67%
CYP1A2 inhibition	-	0.6071	60.71%
CYP2C8 inhibition	-	0.6309	63.09%
CYP inhibitory promiscuity	-	0.8139	81.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9168	91.68%
Carcinogenicity (trinary)	Non-required	0.6553	65.53%
Eye corrosion	-	0.8964	89.64%
Eye irritation	-	0.7482	74.82%
Skin irritation	-	0.7329	73.29%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5073	50.73%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.5647	56.47%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6008	60.08%
Acute Oral Toxicity (c)	III	0.5552	55.52%
Estrogen receptor binding	-	0.5744	57.44%
Androgen receptor binding	+	0.6584	65.84%
Thyroid receptor binding	+	0.5255	52.55%
Glucocorticoid receptor binding	+	0.5852	58.52%
Aromatase binding	-	0.6262	62.62%
PPAR gamma	+	0.5365	53.65%
Honey bee toxicity	-	0.5603	56.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9675	96.75%

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	94.32%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.32%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.32%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.34%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.07%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.47%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.33%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	85.08%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	83.28%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.74%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.51%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	81.36%	83.82%
CHEMBL2581	P07339	Cathepsin D	81.27%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.74%	95.89%

Plants that contains it

• Zinnia elegans

Cross-Links

• PubChem: 163005645
• LOTUS: LTS0252764
• wikiData: Q104976314