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

Details

• Internal ID: dfdd4300-7ba0-4e19-a122-6174c2007d25
• 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,3S)-2,3-dihydroxy-2-methylbutanoyl]oxy-10-methyl-5-[(2R)-2-methylbutanoyl]oxy-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2C(C=C(CCC=C1C(=O)OC)C)OC(=O)C2=C)OC(=O)C(C)(C(C)O)O
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]/1[C@H]([C@@H]2[C@@H](/C=C(\CC/C=C1/C(=O)OC)/C)OC(=O)C2=C)OC(=O)[C@](C)([C@H](C)O)O
• InChI: InChI=1S/C26H36O10/c1-8-14(3)22(28)35-20-17(24(30)33-7)11-9-10-13(2)12-18-19(15(4)23(29)34-18)21(20)36-25(31)26(6,32)16(5)27/h11-12,14,16,18-21,27,32H,4,8-10H2,1-3,5-7H3/b13-12-,17-11+/t14-,16+,18-,19+,20+,21+,26+/m1/s1
• InChI Key: WCLMXJUYTOWYKJ-BGKBWHSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₀
• Molecular Weight: 508.60 g/mol
• Exact Mass: 508.23084734 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9654	96.54%
Caco-2	-	0.6819	68.19%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5321	53.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8258	82.58%
OATP1B3 inhibitior	+	0.8829	88.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8761	87.61%
P-glycoprotein inhibitior	+	0.7541	75.41%
P-glycoprotein substrate	+	0.5551	55.51%
CYP3A4 substrate	+	0.6675	66.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9036	90.36%
CYP3A4 inhibition	-	0.5550	55.50%
CYP2C9 inhibition	-	0.7259	72.59%
CYP2C19 inhibition	-	0.7165	71.65%
CYP2D6 inhibition	-	0.9102	91.02%
CYP1A2 inhibition	-	0.5566	55.66%
CYP2C8 inhibition	+	0.6341	63.41%
CYP inhibitory promiscuity	-	0.8666	86.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5280	52.80%
Eye corrosion	-	0.9751	97.51%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.5910	59.10%
Skin corrosion	-	0.8979	89.79%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4388	43.88%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.7519	75.19%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7175	71.75%
Acute Oral Toxicity (c)	III	0.4660	46.60%
Estrogen receptor binding	+	0.7818	78.18%
Androgen receptor binding	+	0.6088	60.88%
Thyroid receptor binding	+	0.5539	55.39%
Glucocorticoid receptor binding	+	0.7910	79.10%
Aromatase binding	+	0.6199	61.99%
PPAR gamma	+	0.7536	75.36%
Honey bee toxicity	-	0.7239	72.39%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9698	96.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.23%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.89%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.25%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.90%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.28%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.68%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.01%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	90.98%	97.79%
CHEMBL4040	P28482	MAP kinase ERK2	87.98%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.38%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.34%	97.14%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.12%	90.93%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.75%	98.75%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.14%	95.71%
CHEMBL5028	O14672	ADAM10	83.92%	97.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.80%	93.03%
CHEMBL5255	O00206	Toll-like receptor 4	82.80%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.04%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.90%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.85%	94.33%
CHEMBL4588	P22894	Matrix metalloproteinase 8	81.54%	94.66%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.12%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.04%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.40%	93.56%

Plants that contains it

• Tetragonotheca ludoviciana

Cross-Links

• PubChem: 162926994
• LOTUS: LTS0136323
• wikiData: Q105301864