(9-acetyloxy-4,8-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) 2-methylbutanoate

Details

• Internal ID: 22f6bda3-5b03-4dcc-959b-02e4795b0d08
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (9-acetyloxy-4,8-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) 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C2(C1C(C(C3C(C2OC(=O)C)C(=C)C(=O)O3)O)C)C)O
• SMILES (Isomeric): CCC(C)C(=O)OC1CC(C2(C1C(C(C3C(C2OC(=O)C)C(=C)C(=O)O3)O)C)C)O
• InChI: InChI=1S/C22H32O8/c1-7-9(2)20(26)29-13-8-14(24)22(6)16(13)11(4)17(25)18-15(10(3)21(27)30-18)19(22)28-12(5)23/h9,11,13-19,24-25H,3,7-8H2,1-2,4-6H3
• InChI Key: MFFGHSQBNUURJR-UHFFFAOYSA-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	+	0.9873	98.73%
Caco-2	-	0.6518	65.18%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4112	41.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8498	84.98%
OATP1B3 inhibitior	+	0.8886	88.86%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8494	84.94%
P-glycoprotein inhibitior	-	0.5299	52.99%
P-glycoprotein substrate	-	0.5000	50.00%
CYP3A4 substrate	+	0.6429	64.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	+	0.5457	54.57%
CYP2C9 inhibition	-	0.7938	79.38%
CYP2C19 inhibition	-	0.7609	76.09%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	-	0.7118	71.18%
CYP2C8 inhibition	-	0.6508	65.08%
CYP inhibitory promiscuity	-	0.8997	89.97%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5083	50.83%
Eye corrosion	-	0.9805	98.05%
Eye irritation	-	0.8991	89.91%
Skin irritation	-	0.5149	51.49%
Skin corrosion	-	0.8906	89.06%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7393	73.93%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.6932	69.32%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5286	52.86%
Acute Oral Toxicity (c)	III	0.4419	44.19%
Estrogen receptor binding	+	0.7575	75.75%
Androgen receptor binding	+	0.6164	61.64%
Thyroid receptor binding	+	0.5559	55.59%
Glucocorticoid receptor binding	+	0.6055	60.55%
Aromatase binding	+	0.5728	57.28%
PPAR gamma	+	0.5452	54.52%
Honey bee toxicity	-	0.6524	65.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9706	97.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.96%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	97.96%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.52%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.51%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.16%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.38%	98.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.89%	96.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.38%	85.14%
CHEMBL299	P17252	Protein kinase C alpha	88.03%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.59%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.04%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.97%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.05%	99.23%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.91%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.02%	89.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.49%	95.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.01%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.97%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.45%	95.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.29%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	80.66%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.58%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.15%	95.56%

Plants that contains it

• Gaillardia aristata
• Helenium argentinum

Cross-Links

• PubChem: 162981129
• LOTUS: LTS0122810
• wikiData: Q105162624