[(3aR,4S,6aR,8S,9aR,9bR)-8-acetyloxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate

Details

• Internal ID: 7c3d6fe9-7bd0-4379-a02d-6811f1813f77
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-8-acetyloxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
• InChI: InChI=1S/C21H24O6/c1-9(2)20(23)26-16-7-10(3)14-8-15(25-13(6)22)11(4)17(14)19-18(16)12(5)21(24)27-19/h14-19H,1,3-5,7-8H2,2,6H3/t14-,15-,16-,17-,18+,19+/m0/s1
• InChI Key: AXDVLGOQNGOYCX-XREYTECCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.40 g/mol
• Exact Mass: 372.15728848 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 6
• 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	+	0.9871	98.71%
Caco-2	-	0.6064	60.64%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5821	58.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5559	55.59%
P-glycoprotein inhibitior	-	0.6058	60.58%
P-glycoprotein substrate	-	0.6033	60.33%
CYP3A4 substrate	+	0.6436	64.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8884	88.84%
CYP3A4 inhibition	-	0.5677	56.77%
CYP2C9 inhibition	-	0.8624	86.24%
CYP2C19 inhibition	-	0.7339	73.39%
CYP2D6 inhibition	-	0.9533	95.33%
CYP1A2 inhibition	-	0.6311	63.11%
CYP2C8 inhibition	-	0.6948	69.48%
CYP inhibitory promiscuity	-	0.7423	74.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9368	93.68%
Carcinogenicity (trinary)	Non-required	0.5708	57.08%
Eye corrosion	-	0.8835	88.35%
Eye irritation	-	0.6329	63.29%
Skin irritation	-	0.6643	66.43%
Skin corrosion	-	0.9043	90.43%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4495	44.95%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.7408	74.08%
skin sensitisation	-	0.6360	63.60%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.8063	80.63%
Acute Oral Toxicity (c)	II	0.4017	40.17%
Estrogen receptor binding	+	0.7301	73.01%
Androgen receptor binding	+	0.5636	56.36%
Thyroid receptor binding	-	0.5153	51.53%
Glucocorticoid receptor binding	+	0.7428	74.28%
Aromatase binding	-	0.6195	61.95%
PPAR gamma	+	0.6454	64.54%
Honey bee toxicity	-	0.5589	55.89%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9784	97.84%

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	93.60%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	93.57%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.09%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.46%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.68%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	84.23%	91.19%
CHEMBL2581	P07339	Cathepsin D	82.10%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.03%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.84%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.15%	89.00%

Plants that contains it

• Vernonanthura montevidensis

Cross-Links

• PubChem: 14137178
• LOTUS: LTS0011436
• wikiData: Q104920477