[(3aR,4R,6aR,7R,9aS,9bS)-7,9a-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 5d03646d-7fb1-48da-9b5d-bab526c0a6ac
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,7R,9aS,9bS)-7,9a-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H24O6/c1-6-9(2)18(22)25-14-7-10(3)16-13(21)8-11(4)20(16,24)17-15(14)12(5)19(23)26-17/h6,8,13-17,21,24H,3,5,7H2,1-2,4H3/b9-6-/t13-,14-,15-,16-,17+,20-/m1/s1
• InChI Key: GBOICSBDXZIUKE-WMNAQBTMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.59
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8791	87.91%
Caco-2	-	0.6668	66.68%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5457	54.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9011	90.11%
OATP1B3 inhibitior	+	0.9263	92.63%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7385	73.85%
P-glycoprotein inhibitior	-	0.6356	63.56%
P-glycoprotein substrate	-	0.6598	65.98%
CYP3A4 substrate	+	0.6349	63.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8860	88.60%
CYP3A4 inhibition	-	0.7351	73.51%
CYP2C9 inhibition	-	0.8605	86.05%
CYP2C19 inhibition	-	0.8466	84.66%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.8289	82.89%
CYP2C8 inhibition	-	0.7144	71.44%
CYP inhibitory promiscuity	-	0.8207	82.07%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.4358	43.58%
Eye corrosion	-	0.9694	96.94%
Eye irritation	-	0.8487	84.87%
Skin irritation	-	0.6440	64.40%
Skin corrosion	-	0.9017	90.17%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5802	58.02%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.7169	71.69%
skin sensitisation	-	0.7372	73.72%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7354	73.54%
Acute Oral Toxicity (c)	III	0.3137	31.37%
Estrogen receptor binding	+	0.6819	68.19%
Androgen receptor binding	+	0.6033	60.33%
Thyroid receptor binding	-	0.5137	51.37%
Glucocorticoid receptor binding	+	0.5789	57.89%
Aromatase binding	-	0.5629	56.29%
PPAR gamma	+	0.5516	55.16%
Honey bee toxicity	-	0.6694	66.94%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8880	88.80%

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	96.45%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.79%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.32%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.75%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.17%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.24%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.37%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.11%	91.07%
CHEMBL1902	P62942	FK506-binding protein 1A	81.68%	97.05%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.42%	95.50%

Plants that contains it

• Eupatorium rotundifolium

Cross-Links

• PubChem: 162916106
• LOTUS: LTS0005194
• wikiData: Q105006007