[(3aR,4R,6aS,9S,9aS,9bS)-6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 68b27c7c-8831-4973-b1af-b5372b1e464d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aS,9S,9aS,9bS)-6a,9-dihydroxy-9-methyl-3,6-dimethylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H24O6/c1-6-10(2)17(21)25-13-9-11(3)20(24)8-7-19(5,23)16(20)15-14(13)12(4)18(22)26-15/h6-8,13-16,23-24H,3-4,9H2,1-2,5H3/b10-6+/t13-,14-,15+,16+,19+,20-/m1/s1
• InChI Key: ZAUUUXKGZYJFFX-YKVHEDJXSA-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: 1.40
• 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	+	0.9514	95.14%
Caco-2	-	0.6174	61.74%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5972	59.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8849	88.49%
OATP1B3 inhibitior	+	0.9026	90.26%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8188	81.88%
P-glycoprotein inhibitior	-	0.5983	59.83%
P-glycoprotein substrate	-	0.7520	75.20%
CYP3A4 substrate	+	0.6302	63.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8930	89.30%
CYP3A4 inhibition	-	0.7805	78.05%
CYP2C9 inhibition	-	0.8517	85.17%
CYP2C19 inhibition	-	0.8718	87.18%
CYP2D6 inhibition	-	0.9521	95.21%
CYP1A2 inhibition	-	0.8211	82.11%
CYP2C8 inhibition	-	0.7241	72.41%
CYP inhibitory promiscuity	-	0.8707	87.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9268	92.68%
Carcinogenicity (trinary)	Non-required	0.4700	47.00%
Eye corrosion	-	0.9629	96.29%
Eye irritation	-	0.8592	85.92%
Skin irritation	-	0.6330	63.30%
Skin corrosion	-	0.8905	89.05%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4423	44.23%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.7428	74.28%
skin sensitisation	-	0.7085	70.85%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.8479	84.79%
Acute Oral Toxicity (c)	II	0.3559	35.59%
Estrogen receptor binding	+	0.6346	63.46%
Androgen receptor binding	+	0.6271	62.71%
Thyroid receptor binding	+	0.6458	64.58%
Glucocorticoid receptor binding	+	0.5422	54.22%
Aromatase binding	-	0.5443	54.43%
PPAR gamma	+	0.5786	57.86%
Honey bee toxicity	-	0.6188	61.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9148	91.48%

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	98.01%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.57%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	93.17%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.38%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.57%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.88%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.97%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.17%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.89%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.89%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.78%	97.25%

Plants that contains it

• Calea solidaginea

Cross-Links

• PubChem: 162974821
• LOTUS: LTS0124567
• wikiData: Q105370154