[(3aR,4R,5S,5aS,6S,8R,8aR,9R,9aS)-8-acetyloxy-4,9-dihydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 6216bfb3-2beb-49a8-8576-7dcf459d72bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aR,4R,5S,5aS,6S,8R,8aR,9R,9aS)-8-acetyloxy-4,9-dihydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C2(C1C(C(C3C(C2O)C(=C)C(=O)O3)O)C)C)OC(=O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1C[C@H]([C@@]2([C@@H]1[C@@H]([C@H]([C@H]3[C@H]([C@H]2O)C(=C)C(=O)O3)O)C)C)OC(=O)C
• InChI: InChI=1S/C22H32O8/c1-7-9(2)20(26)29-13-8-14(28-12(5)23)22(6)16(13)11(4)17(24)18-15(19(22)25)10(3)21(27)30-18/h9,11,13-19,24-25H,3,7-8H2,1-2,4-6H3/t9-,11+,13+,14-,15-,16-,17-,18-,19-,22-/m1/s1
• InChI Key: WZXOOHRYBWQIBX-ZGWYANJFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₈
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.20971797 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9738	97.38%
Caco-2	-	0.7042	70.42%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4602	46.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8553	85.53%
OATP1B3 inhibitior	+	0.8485	84.85%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7446	74.46%
P-glycoprotein inhibitior	-	0.5215	52.15%
P-glycoprotein substrate	-	0.5639	56.39%
CYP3A4 substrate	+	0.6505	65.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	+	0.5523	55.23%
CYP2C9 inhibition	-	0.6947	69.47%
CYP2C19 inhibition	-	0.6413	64.13%
CYP2D6 inhibition	-	0.9342	93.42%
CYP1A2 inhibition	-	0.5702	57.02%
CYP2C8 inhibition	-	0.6599	65.99%
CYP inhibitory promiscuity	-	0.7736	77.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5036	50.36%
Eye corrosion	-	0.9809	98.09%
Eye irritation	-	0.8975	89.75%
Skin irritation	-	0.5335	53.35%
Skin corrosion	-	0.8943	89.43%
Ames mutagenesis	-	0.6264	62.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6175	61.75%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6388	63.88%
skin sensitisation	-	0.7246	72.46%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.5830	58.30%
Acute Oral Toxicity (c)	III	0.3793	37.93%
Estrogen receptor binding	+	0.7785	77.85%
Androgen receptor binding	+	0.5671	56.71%
Thyroid receptor binding	+	0.5512	55.12%
Glucocorticoid receptor binding	+	0.5701	57.01%
Aromatase binding	+	0.5476	54.76%
PPAR gamma	+	0.5867	58.67%
Honey bee toxicity	-	0.6694	66.94%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9818	98.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.77%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.63%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.55%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.53%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.58%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	94.42%	97.79%
CHEMBL2581	P07339	Cathepsin D	91.99%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.52%	86.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.60%	96.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.12%	89.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.75%	89.00%
CHEMBL299	P17252	Protein kinase C alpha	84.55%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.29%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.96%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	81.52%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.75%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.71%	98.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.56%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.40%	97.14%

Plants that contains it

• Gaillardia pulchella

Cross-Links

• PubChem: 162993386
• LOTUS: LTS0040046
• wikiData: Q105323623