[(3aR,4aS,6S,7S,8R,8aR,9aR)-8-acetyloxy-7-hydroxy-8a-methyl-3,5-dimethylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-6-yl] 3-methylbutanoate

Details

• Internal ID: 06fb760a-ee1c-417f-a5a5-9539c031cd38
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aR,4aS,6S,7S,8R,8aR,9aR)-8-acetyloxy-7-hydroxy-8a-methyl-3,5-dimethylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-6-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C(C(C2(CC3C(CC2C1=C)C(=C)C(=O)O3)C)OC(=O)C)O
• SMILES (Isomeric): CC(C)CC(=O)O[C@@H]1[C@@H]([C@@H]([C@@]2(C[C@@H]3[C@H](C[C@H]2C1=C)C(=C)C(=O)O3)C)OC(=O)C)O
• InChI: InChI=1S/C22H30O7/c1-10(2)7-17(24)29-19-12(4)15-8-14-11(3)21(26)28-16(14)9-22(15,6)20(18(19)25)27-13(5)23/h10,14-16,18-20,25H,3-4,7-9H2,1-2,5-6H3/t14-,15+,16-,18+,19+,20+,22-/m1/s1
• InChI Key: JEWFEUSWMIUOOI-SVCQRJFZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₇
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.19915329 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9838	98.38%
Caco-2	-	0.6963	69.63%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6596	65.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8409	84.09%
OATP1B3 inhibitior	-	0.2720	27.20%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6243	62.43%
P-glycoprotein inhibitior	-	0.4592	45.92%
P-glycoprotein substrate	-	0.5528	55.28%
CYP3A4 substrate	+	0.6559	65.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.5257	52.57%
CYP2C9 inhibition	-	0.8170	81.70%
CYP2C19 inhibition	-	0.7889	78.89%
CYP2D6 inhibition	-	0.9330	93.30%
CYP1A2 inhibition	-	0.8063	80.63%
CYP2C8 inhibition	-	0.6663	66.63%
CYP inhibitory promiscuity	-	0.6622	66.22%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5052	50.52%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8715	87.15%
Skin irritation	-	0.5608	56.08%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5337	53.37%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.6881	68.81%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6514	65.14%
Acute Oral Toxicity (c)	III	0.4377	43.77%
Estrogen receptor binding	+	0.7509	75.09%
Androgen receptor binding	+	0.6729	67.29%
Thyroid receptor binding	+	0.5219	52.19%
Glucocorticoid receptor binding	+	0.7321	73.21%
Aromatase binding	+	0.5552	55.52%
PPAR gamma	+	0.6084	60.84%
Honey bee toxicity	-	0.7010	70.10%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9972	99.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.87%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.63%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.59%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.88%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	95.76%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	95.63%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.02%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.37%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.65%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.28%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.54%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.86%	91.24%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.27%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.49%	97.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.46%	96.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.87%	89.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.52%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.51%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.63%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.64%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.34%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.17%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.11%	95.89%

Plants that contains it

• Blumea densiflora

Cross-Links

• PubChem: 163015304
• LOTUS: LTS0189696
• wikiData: Q105126475