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

Details

• Internal ID: 7bdf0c75-14b9-445b-aa45-4729961ac671
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(4aR,5S,6R,8aR,9aS)-5-acetyloxy-9a-methoxy-3,5,8a-trimethyl-2-oxo-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-6-yl] (2S,3S)-3-acetyloxy-2-hydroxy-2-methylbutanoate
• InChI: InChI=1S/C25H36O10/c1-13-17-11-18-22(5,12-25(17,31-8)35-20(13)28)10-9-19(24(18,7)34-16(4)27)33-21(29)23(6,30)14(2)32-15(3)26/h14,18-19,30H,9-12H2,1-8H3/t14-,18+,19+,22+,23-,24-,25-/m0/s1
• InChI Key: QLMXHUYYSGPPTL-NNVRNGBHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₁₀
• Molecular Weight: 496.50 g/mol
• Exact Mass: 496.23084734 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	-	0.6474	64.74%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7035	70.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8568	85.68%
OATP1B3 inhibitior	+	0.9383	93.83%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.7851	78.51%
P-glycoprotein inhibitior	+	0.7331	73.31%
P-glycoprotein substrate	-	0.5856	58.56%
CYP3A4 substrate	+	0.7100	71.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9041	90.41%
CYP3A4 inhibition	-	0.7141	71.41%
CYP2C9 inhibition	-	0.8844	88.44%
CYP2C19 inhibition	-	0.9244	92.44%
CYP2D6 inhibition	-	0.9569	95.69%
CYP1A2 inhibition	-	0.5194	51.94%
CYP2C8 inhibition	+	0.6078	60.78%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4803	48.03%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8739	87.39%
Skin irritation	+	0.5479	54.79%
Skin corrosion	-	0.9159	91.59%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6622	66.22%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5321	53.21%
skin sensitisation	-	0.8673	86.73%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6876	68.76%
Acute Oral Toxicity (c)	III	0.3537	35.37%
Estrogen receptor binding	+	0.7753	77.53%
Androgen receptor binding	+	0.6974	69.74%
Thyroid receptor binding	+	0.6311	63.11%
Glucocorticoid receptor binding	+	0.7634	76.34%
Aromatase binding	+	0.6984	69.84%
PPAR gamma	+	0.7064	70.64%
Honey bee toxicity	-	0.7129	71.29%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9872	98.72%

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	98.27%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.67%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.98%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	93.52%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.51%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.37%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.41%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	90.66%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.79%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	88.30%	83.82%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.72%	92.62%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.66%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.53%	95.89%
CHEMBL299	P17252	Protein kinase C alpha	85.25%	98.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.38%	93.56%
CHEMBL204	P00734	Thrombin	83.43%	96.01%
CHEMBL340	P08684	Cytochrome P450 3A4	83.27%	91.19%
CHEMBL5028	O14672	ADAM10	82.75%	97.50%
CHEMBL1937	Q92769	Histone deacetylase 2	81.90%	94.75%
CHEMBL1902	P62942	FK506-binding protein 1A	81.78%	97.05%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.37%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.70%	93.03%

Plants that contains it

• Tessaria fastigiata

Cross-Links

• PubChem: 163036196
• LOTUS: LTS0092600
• wikiData: Q105223662