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

Details

• Internal ID: 8136a36c-fb51-4f67-8c03-49c155d00343
• 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-hydroxy-3,5,8a-trimethyl-2-oxo-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-6-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2CCC3(CC4(C(=C(C(=O)O4)C)CC3C2(C)OC(=O)C)O)C
• SMILES (Isomeric): C[C@@H]1[C@@](O1)(C)C(=O)O[C@@H]2CC[C@@]3(C[C@]4(C(=C(C(=O)O4)C)C[C@H]3[C@]2(C)OC(=O)C)O)C
• InChI: InChI=1S/C22H30O8/c1-11-14-9-15-19(4,10-22(14,26)30-17(11)24)8-7-16(21(15,6)29-13(3)23)27-18(25)20(5)12(2)28-20/h12,15-16,26H,7-10H2,1-6H3/t12-,15-,16-,19-,20+,21+,22+/m1/s1
• InChI Key: XSNMFQOTAYCACP-JWGPCJDDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₈
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.19406791 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.17
• 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	+	0.9891	98.91%
Caco-2	+	0.5790	57.90%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8069	80.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8799	87.99%
OATP1B3 inhibitior	+	0.8264	82.64%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.6124	61.24%
BSEP inhibitior	+	0.6217	62.17%
P-glycoprotein inhibitior	+	0.6403	64.03%
P-glycoprotein substrate	-	0.6891	68.91%
CYP3A4 substrate	+	0.6992	69.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8901	89.01%
CYP3A4 inhibition	-	0.5609	56.09%
CYP2C9 inhibition	-	0.7637	76.37%
CYP2C19 inhibition	-	0.8220	82.20%
CYP2D6 inhibition	-	0.9432	94.32%
CYP1A2 inhibition	-	0.6474	64.74%
CYP2C8 inhibition	+	0.4544	45.44%
CYP inhibitory promiscuity	-	0.9322	93.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4109	41.09%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8732	87.32%
Skin irritation	+	0.5971	59.71%
Skin corrosion	-	0.9025	90.25%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5349	53.49%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5127	51.27%
skin sensitisation	-	0.8556	85.56%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5636	56.36%
Acute Oral Toxicity (c)	IV	0.3002	30.02%
Estrogen receptor binding	+	0.8500	85.00%
Androgen receptor binding	+	0.7221	72.21%
Thyroid receptor binding	+	0.6662	66.62%
Glucocorticoid receptor binding	+	0.7052	70.52%
Aromatase binding	+	0.6262	62.62%
PPAR gamma	+	0.7235	72.35%
Honey bee toxicity	-	0.7816	78.16%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5950	59.50%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.44%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.72%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.08%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.37%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.13%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.15%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.66%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.16%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.31%	97.25%
CHEMBL299	P17252	Protein kinase C alpha	87.99%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.88%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.94%	93.03%
CHEMBL5028	O14672	ADAM10	82.81%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.31%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	82.08%	97.79%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	80.58%	88.42%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.09%	82.69%

Plants that contains it

• Pluchea baccharis

Cross-Links

• PubChem: 162911692
• LOTUS: LTS0115483
• wikiData: Q105341118