4-Acetoxy-2-(hydroxymethyl)-2-butenoic acid [(3aR,3abeta,4S,9abeta,9balpha)-2-oxo-3-methylene-5aalpha-methyl-6alpha-hydroxy-9alpha-formyldodecahydronaphtho[1,2-b]furan]-4beta-yl ester

Details

• Internal ID: e3884acf-2e98-4708-ac99-53ed73eecf30
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl] (E)-4-acetyloxy-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC(=O)OCC=C(CO)C(=O)OC1CC2(C(CCC(C2C3C1C(=C)C(=O)O3)C=O)O)C
• SMILES (Isomeric): CC(=O)OC/C=C(\CO)/C(=O)O[C@H]1C[C@]2([C@@H](CC[C@@H]([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)C=O)O)C
• InChI: InChI=1S/C22H28O9/c1-11-17-15(30-21(28)14(10-24)6-7-29-12(2)25)8-22(3)16(26)5-4-13(9-23)18(22)19(17)31-20(11)27/h6,9,13,15-19,24,26H,1,4-5,7-8,10H2,2-3H3/b14-6+/t13-,15+,16-,17-,18-,19+,22+/m1/s1
• InChI Key: MBXJTNWCNHRTMO-AVNDKTAWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₉
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.17333247 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.47
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9702	97.02%
Caco-2	-	0.7189	71.89%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8011	80.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8675	86.75%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.5441	54.41%
BSEP inhibitior	+	0.6910	69.10%
P-glycoprotein inhibitior	-	0.4491	44.91%
P-glycoprotein substrate	+	0.5199	51.99%
CYP3A4 substrate	+	0.7027	70.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9003	90.03%
CYP3A4 inhibition	+	0.5120	51.20%
CYP2C9 inhibition	-	0.8735	87.35%
CYP2C19 inhibition	-	0.8939	89.39%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.8395	83.95%
CYP2C8 inhibition	+	0.4560	45.60%
CYP inhibitory promiscuity	-	0.8603	86.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5827	58.27%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9395	93.95%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4350	43.50%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6303	63.03%
skin sensitisation	-	0.9065	90.65%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.8132	81.32%
Acute Oral Toxicity (c)	III	0.4158	41.58%
Estrogen receptor binding	+	0.8617	86.17%
Androgen receptor binding	+	0.6496	64.96%
Thyroid receptor binding	-	0.4893	48.93%
Glucocorticoid receptor binding	+	0.7743	77.43%
Aromatase binding	+	0.6555	65.55%
PPAR gamma	+	0.6154	61.54%
Honey bee toxicity	-	0.6967	69.67%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9928	99.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.72%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.68%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.96%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.01%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.42%	95.56%
CHEMBL1871	P10275	Androgen Receptor	88.22%	96.43%
CHEMBL5028	O14672	ADAM10	87.64%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.59%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.46%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.99%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.21%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.17%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.93%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	83.05%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.70%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	82.40%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.33%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.72%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	80.47%	97.79%

Plants that contains it

• Centaurea spinosa

Cross-Links

• PubChem: 101772673
• LOTUS: LTS0117426
• wikiData: Q105161022