[(3aS,4R,4aS,5R,8R,8aR,9R,9aS)-9-acetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-4-[(2-methylpropan-2-yl)oxy]-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8-yl] acetate

Details

• Internal ID: 976c4de8-4fa6-422c-a69d-da2bd46d918b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,4R,4aS,5R,8R,8aR,9R,9aS)-9-acetyloxy-5-hydroxy-5,8a-dimethyl-3-methylidene-4-[(2-methylpropan-2-yl)oxy]-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-8-yl] acetate
• SMILES (Canonical): CC(=O)OC1CCC(C2C1(C(C3C(C2OC(C)(C)C)C(=C)C(=O)O3)OC(=O)C)C)(C)O
• SMILES (Isomeric): CC(=O)O[C@@H]1CC[C@@]([C@H]2[C@]1([C@H]([C@@H]3[C@H]([C@H]2OC(C)(C)C)C(=C)C(=O)O3)OC(=O)C)C)(C)O
• InChI: InChI=1S/C23H34O8/c1-11-15-16(31-21(4,5)6)18-22(7,27)10-9-14(28-12(2)24)23(18,8)19(29-13(3)25)17(15)30-20(11)26/h14-19,27H,1,9-10H2,2-8H3/t14-,15+,16-,17+,18+,19+,22-,23+/m1/s1
• InChI Key: RSVFIQLZRMUDJC-WPYHGQKCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₈
• Molecular Weight: 438.50 g/mol
• Exact Mass: 438.22536804 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.31
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	-	0.5372	53.72%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6989	69.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8802	88.02%
OATP1B3 inhibitior	-	0.2789	27.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6532	65.32%
BSEP inhibitior	-	0.8443	84.43%
P-glycoprotein inhibitior	+	0.6449	64.49%
P-glycoprotein substrate	-	0.7565	75.65%
CYP3A4 substrate	+	0.6785	67.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8995	89.95%
CYP3A4 inhibition	+	0.5995	59.95%
CYP2C9 inhibition	-	0.7598	75.98%
CYP2C19 inhibition	-	0.8272	82.72%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	-	0.7396	73.96%
CYP2C8 inhibition	+	0.4784	47.84%
CYP inhibitory promiscuity	-	0.9136	91.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5244	52.44%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.8546	85.46%
Skin irritation	+	0.5223	52.23%
Skin corrosion	-	0.8377	83.77%
Ames mutagenesis	-	0.7023	70.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.4622	46.22%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.6085	60.85%
skin sensitisation	-	0.6977	69.77%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.8170	81.70%
Acute Oral Toxicity (c)	III	0.4054	40.54%
Estrogen receptor binding	+	0.8574	85.74%
Androgen receptor binding	+	0.6531	65.31%
Thyroid receptor binding	+	0.6451	64.51%
Glucocorticoid receptor binding	+	0.5608	56.08%
Aromatase binding	+	0.5470	54.70%
PPAR gamma	+	0.7756	77.56%
Honey bee toxicity	-	0.6580	65.80%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6153	61.53%
Fish aquatic toxicity	+	0.9850	98.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.19%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.71%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.16%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.73%	97.14%
CHEMBL2581	P07339	Cathepsin D	90.64%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.98%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	87.76%	97.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.59%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.24%	96.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.05%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.98%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	84.94%	91.19%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.83%	93.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.47%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.95%	93.04%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.70%	91.07%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.59%	92.94%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.04%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.77%	100.00%
CHEMBL5028	O14672	ADAM10	80.94%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.71%	97.09%

Plants that contains it

• Sphagneticola trilobata

Cross-Links

• PubChem: 162877907
• LOTUS: LTS0258313
• wikiData: Q105244897