methyl (3aS,4S,5S,6E,10Z,11aR)-4-[(2S,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-5-[(2R,3S)-3-hydroxy-2-methylbutanoyl]oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate

Details

• Internal ID: 3ac20ee5-a0a3-4271-97c4-7a2bede6c2d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (3aS,4S,5S,6E,10Z,11aR)-4-[(2S,3R)-2,3-dimethyloxirane-2-carbonyl]oxy-5-[(2R,3S)-3-hydroxy-2-methylbutanoyl]oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2C3C(C=C(CCC=C(C2OC(=O)C(C)C(C)O)C(=O)OC)C)OC(=O)C3=C
• SMILES (Isomeric): C[C@@H]1[C@@](O1)(C)C(=O)O[C@H]2[C@@H]3[C@@H](/C=C(\CC/C=C(\[C@@H]2OC(=O)[C@H](C)[C@H](C)O)/C(=O)OC)/C)OC(=O)C3=C
• InChI: InChI=1S/C26H34O10/c1-12-9-8-10-17(24(30)32-7)20(34-22(28)13(2)15(4)27)21(35-25(31)26(6)16(5)36-26)19-14(3)23(29)33-18(19)11-12/h10-11,13,15-16,18-21,27H,3,8-9H2,1-2,4-7H3/b12-11-,17-10+/t13-,15+,16-,18-,19+,20+,21+,26+/m1/s1
• InChI Key: LRTMGMWLZYDWGF-WYKAAAIPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₀
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.21519728 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.94
• 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	+	0.9727	97.27%
Caco-2	-	0.6595	65.95%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5687	56.87%
OATP2B1 inhibitior	-	0.8622	86.22%
OATP1B1 inhibitior	+	0.8496	84.96%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7771	77.71%
BSEP inhibitior	+	0.7555	75.55%
P-glycoprotein inhibitior	+	0.7741	77.41%
P-glycoprotein substrate	+	0.5390	53.90%
CYP3A4 substrate	+	0.6954	69.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8960	89.60%
CYP3A4 inhibition	-	0.6585	65.85%
CYP2C9 inhibition	-	0.8562	85.62%
CYP2C19 inhibition	-	0.8657	86.57%
CYP2D6 inhibition	-	0.9178	91.78%
CYP1A2 inhibition	-	0.5583	55.83%
CYP2C8 inhibition	+	0.5559	55.59%
CYP inhibitory promiscuity	-	0.9380	93.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4386	43.86%
Eye corrosion	-	0.9701	97.01%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.6182	61.82%
Skin corrosion	-	0.8868	88.68%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7255	72.55%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6034	60.34%
Acute Oral Toxicity (c)	III	0.4251	42.51%
Estrogen receptor binding	+	0.7960	79.60%
Androgen receptor binding	+	0.6334	63.34%
Thyroid receptor binding	+	0.5905	59.05%
Glucocorticoid receptor binding	+	0.7851	78.51%
Aromatase binding	+	0.6150	61.50%
PPAR gamma	+	0.8015	80.15%
Honey bee toxicity	-	0.6580	65.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9377	93.77%

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	99.31%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.90%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.84%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	93.96%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.98%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.94%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	91.11%	90.17%
CHEMBL230	P35354	Cyclooxygenase-2	90.92%	89.63%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.41%	97.14%
CHEMBL4208	P20618	Proteasome component C5	89.81%	90.00%
CHEMBL299	P17252	Protein kinase C alpha	89.04%	98.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.70%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.37%	95.56%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.34%	95.71%
CHEMBL2581	P07339	Cathepsin D	87.18%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.82%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	86.24%	97.79%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.74%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.61%	86.33%
CHEMBL5028	O14672	ADAM10	84.42%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.38%	91.07%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.26%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.51%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.49%	91.24%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.33%	93.56%
CHEMBL5255	O00206	Toll-like receptor 4	82.10%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	81.71%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	81.34%	91.19%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.62%	98.75%
CHEMBL301	P24941	Cyclin-dependent kinase 2	80.08%	91.23%

Plants that contains it

• Tetragonotheca ludoviciana

Cross-Links

• PubChem: 162871022
• LOTUS: LTS0248315
• wikiData: Q105156314