methyl (3aR,4R,5R,6E,10S,11aS)-5-[(2S)-butan-2-yl]oxy-4-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-6-carboxylate

Details

• Internal ID: 7896a5e7-f5cf-4e03-a04e-44f46624c30b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (3aR,4R,5R,6E,10S,11aS)-5-[(2S)-butan-2-yl]oxy-4-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CCC(C)OC1C(C2C(CC(CCC=C1C(=O)OC)CO)OC(=O)C2=C)OC(=O)C3(C(O3)C)C
• SMILES (Isomeric): CC[C@H](C)O[C@H]/1[C@@H]([C@H]2[C@H](C[C@H](CC/C=C1/C(=O)OC)CO)OC(=O)C2=C)OC(=O)[C@@]3([C@@H](O3)C)C
• InChI: InChI=1S/C25H36O9/c1-7-13(2)31-20-17(23(28)30-6)10-8-9-16(12-26)11-18-19(14(3)22(27)32-18)21(20)33-24(29)25(5)15(4)34-25/h10,13,15-16,18-21,26H,3,7-9,11-12H2,1-2,4-6H3/b17-10+/t13-,15-,16-,18-,19+,20+,21+,25-/m0/s1
• InChI Key: RNWVAMAILZZWBT-PSBFNQLOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₉
• Molecular Weight: 480.50 g/mol
• Exact Mass: 480.23593272 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9605	96.05%
Caco-2	-	0.6104	61.04%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7044	70.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8218	82.18%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.8412	84.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6371	63.71%
P-glycoprotein inhibitior	+	0.6871	68.71%
P-glycoprotein substrate	+	0.6306	63.06%
CYP3A4 substrate	+	0.6855	68.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8820	88.20%
CYP3A4 inhibition	+	0.5494	54.94%
CYP2C9 inhibition	-	0.7025	70.25%
CYP2C19 inhibition	-	0.8004	80.04%
CYP2D6 inhibition	-	0.9223	92.23%
CYP1A2 inhibition	-	0.7447	74.47%
CYP2C8 inhibition	+	0.5887	58.87%
CYP inhibitory promiscuity	-	0.8455	84.55%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.4574	45.74%
Eye corrosion	-	0.9774	97.74%
Eye irritation	-	0.9201	92.01%
Skin irritation	-	0.6511	65.11%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5145	51.45%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6677	66.77%
skin sensitisation	-	0.8390	83.90%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.5834	58.34%
Acute Oral Toxicity (c)	III	0.4953	49.53%
Estrogen receptor binding	+	0.8059	80.59%
Androgen receptor binding	+	0.5944	59.44%
Thyroid receptor binding	+	0.5300	53.00%
Glucocorticoid receptor binding	+	0.8347	83.47%
Aromatase binding	+	0.6595	65.95%
PPAR gamma	+	0.7223	72.23%
Honey bee toxicity	-	0.7267	72.67%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8991	89.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4072	P07858	Cathepsin B	98.22%	93.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.49%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.10%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.27%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	94.85%	97.79%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.89%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.64%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	88.78%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.51%	93.56%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	88.09%	92.88%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.96%	93.03%
CHEMBL299	P17252	Protein kinase C alpha	85.87%	98.03%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.59%	95.83%
CHEMBL4588	P22894	Matrix metalloproteinase 8	85.55%	94.66%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.73%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.10%	95.71%
CHEMBL5255	O00206	Toll-like receptor 4	83.94%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.88%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.56%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	83.05%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.15%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.84%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.78%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.69%	91.24%
CHEMBL5028	O14672	ADAM10	80.30%	97.50%

Plants that contains it

• Tetragonotheca ludoviciana

Cross-Links

• PubChem: 162869644
• LOTUS: LTS0000613
• wikiData: Q105241880