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

Details

• Internal ID: 9558df5f-eb9f-452d-84a6-8d1286bb8198
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-4-acetyloxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C1=C)C3C(C(CC2=C)OC(=O)C)C(=C)C(=O)O3
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@@H]2[C@H](C1=C)[C@@H]3[C@@H]([C@H](CC2=C)OC(=O)C)C(=C)C(=O)O3
• InChI: InChI=1S/C19H22O6/c1-8-6-15(24-12(5)21)17-10(3)19(22)25-18(17)16-9(2)14(7-13(8)16)23-11(4)20/h13-18H,1-3,6-7H2,4-5H3/t13-,14-,15-,16-,17+,18+/m0/s1
• InChI Key: BDUMUWUQRSWNQA-UXJCHEOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.10
• H-Bond Acceptor: 6
• 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	+	0.9871	98.71%
Caco-2	+	0.4907	49.07%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5821	58.21%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9029	90.29%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6893	68.93%
P-glycoprotein inhibitior	-	0.6175	61.75%
P-glycoprotein substrate	-	0.7169	71.69%
CYP3A4 substrate	+	0.6107	61.07%
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	-	0.7872	78.72%
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	-	0.4917	49.17%
Skin irritation	-	0.6643	66.43%
Skin corrosion	-	0.9043	90.43%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5558	55.58%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.7533	75.33%
skin sensitisation	-	0.6360	63.60%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6834	68.34%
Acute Oral Toxicity (c)	II	0.4017	40.17%
Estrogen receptor binding	+	0.7214	72.14%
Androgen receptor binding	+	0.5549	55.49%
Thyroid receptor binding	-	0.5287	52.87%
Glucocorticoid receptor binding	+	0.6959	69.59%
Aromatase binding	-	0.5859	58.59%
PPAR gamma	-	0.5164	51.64%
Honey bee toxicity	-	0.6138	61.38%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.77%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	92.08%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.47%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	84.69%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.54%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.42%	96.09%
CHEMBL2581	P07339	Cathepsin D	82.10%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.40%	97.09%

Plants that contains it

• Conocephalum conicum
• Vernonanthura montevidensis

Cross-Links

• PubChem: 14137176
• LOTUS: LTS0271444
• wikiData: Q104924732