methyl (3aS,4S,5S,6E,11S,11aS)-11-hydroxy-5-[(E)-2-(hydroxymethyl)but-2-enoyl]oxy-3,10-dimethylidene-4-(2-methylpropanoyloxy)-2-oxo-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-6-carboxylate

Details

• Internal ID: 24701931-c2b7-4518-8f9b-66137c05fbdd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: methyl (3aS,4S,5S,6E,11S,11aS)-11-hydroxy-5-[(E)-2-(hydroxymethyl)but-2-enoyl]oxy-3,10-dimethylidene-4-(2-methylpropanoyloxy)-2-oxo-4,5,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CC=C(CO)C(=O)OC1C(C2C(C(C(=C)CCC=C1C(=O)OC)O)OC(=O)C2=C)OC(=O)C(C)C
• SMILES (Isomeric): C/C=C(\CO)/C(=O)O[C@@H]/1[C@H]([C@@H]2[C@@H]([C@H](C(=C)CC/C=C1/C(=O)OC)O)OC(=O)C2=C)OC(=O)C(C)C
• InChI: InChI=1S/C25H32O10/c1-7-15(11-26)24(30)33-19-16(25(31)32-6)10-8-9-13(4)18(27)20-17(14(5)23(29)34-20)21(19)35-22(28)12(2)3/h7,10,12,17-21,26-27H,4-5,8-9,11H2,1-3,6H3/b15-7+,16-10+/t17-,18-,19-,20-,21-/m0/s1
• InChI Key: XMUNLUYNEDVGGM-ONMZSPBZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₀
• Molecular Weight: 492.50 g/mol
• Exact Mass: 492.19954721 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 10
• 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	+	0.9481	94.81%
Caco-2	-	0.7281	72.81%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7217	72.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8441	84.41%
OATP1B3 inhibitior	+	0.9082	90.82%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6249	62.49%
P-glycoprotein inhibitior	+	0.7039	70.39%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6422	64.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9015	90.15%
CYP3A4 inhibition	-	0.7308	73.08%
CYP2C9 inhibition	-	0.6553	65.53%
CYP2C19 inhibition	-	0.7569	75.69%
CYP2D6 inhibition	-	0.8700	87.00%
CYP1A2 inhibition	-	0.5315	53.15%
CYP2C8 inhibition	+	0.4478	44.78%
CYP inhibitory promiscuity	-	0.7974	79.74%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6605	66.05%
Eye corrosion	-	0.9719	97.19%
Eye irritation	-	0.8776	87.76%
Skin irritation	-	0.7063	70.63%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5929	59.29%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8301	83.01%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4877	48.77%
Estrogen receptor binding	+	0.6500	65.00%
Androgen receptor binding	+	0.5396	53.96%
Thyroid receptor binding	-	0.5053	50.53%
Glucocorticoid receptor binding	+	0.7369	73.69%
Aromatase binding	-	0.5574	55.74%
PPAR gamma	+	0.6557	65.57%
Honey bee toxicity	-	0.6921	69.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8914	89.14%

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	96.28%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.86%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.80%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.69%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.75%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.24%	94.73%
CHEMBL299	P17252	Protein kinase C alpha	87.28%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.28%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.84%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.68%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.94%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.92%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.38%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.33%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.24%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.96%	92.62%
CHEMBL5028	O14672	ADAM10	82.73%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.20%	99.23%

Plants that contains it

• Tetragonotheca ludoviciana

Cross-Links

• PubChem: 101532554
• LOTUS: LTS0129677
• wikiData: Q105331427