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

Details

• Internal ID: f6c3afd6-5fb7-4626-81ee-23bbc076697b
• 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)-2-hydroxy-2-methyl-3-oxobutanoyl]oxy-10-methyl-3-methylidene-5-(2-methylpropanoyloxy)-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate
• SMILES (Canonical): CC1=CC2C(C(C(C(=CCC1)C(=O)OC)OC(=O)C(C)C)OC(=O)C(C)(C(=O)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C/[C@@H]2[C@@H]([C@@H]([C@H](/C(=C\CC1)/C(=O)OC)OC(=O)C(C)C)OC(=O)[C@](C)(C(=O)C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C25H32O10/c1-12(2)21(27)34-19-16(23(29)32-7)10-8-9-13(3)11-17-18(14(4)22(28)33-17)20(19)35-24(30)25(6,31)15(5)26/h10-12,17-20,31H,4,8-9H2,1-3,5-7H3/b13-11-,16-10+/t17-,18+,19+,20+,25+/m1/s1
• InChI Key: UYAXGUQGFPEJCB-QBQBJPBOSA-N
• Popularity: 0 references 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): 143.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.74
• 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	+	0.9783	97.83%
Caco-2	-	0.6390	63.90%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6199	61.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8520	85.20%
OATP1B3 inhibitior	+	0.8413	84.13%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8449	84.49%
P-glycoprotein inhibitior	+	0.8179	81.79%
P-glycoprotein substrate	-	0.5486	54.86%
CYP3A4 substrate	+	0.6765	67.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9119	91.19%
CYP3A4 inhibition	-	0.6570	65.70%
CYP2C9 inhibition	-	0.8135	81.35%
CYP2C19 inhibition	-	0.8430	84.30%
CYP2D6 inhibition	-	0.9125	91.25%
CYP1A2 inhibition	-	0.5440	54.40%
CYP2C8 inhibition	+	0.5792	57.92%
CYP inhibitory promiscuity	-	0.9289	92.89%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.5034	50.34%
Eye corrosion	-	0.9650	96.50%
Eye irritation	-	0.8776	87.76%
Skin irritation	-	0.6019	60.19%
Skin corrosion	-	0.8925	89.25%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5241	52.41%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6702	67.02%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6077	60.77%
Acute Oral Toxicity (c)	III	0.4879	48.79%
Estrogen receptor binding	+	0.7875	78.75%
Androgen receptor binding	+	0.6096	60.96%
Thyroid receptor binding	+	0.6164	61.64%
Glucocorticoid receptor binding	+	0.8187	81.87%
Aromatase binding	+	0.5798	57.98%
PPAR gamma	+	0.7721	77.21%
Honey bee toxicity	-	0.6926	69.26%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9618	96.18%

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	97.13%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.83%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.68%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.68%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	92.56%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.06%	96.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	89.13%	90.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.53%	99.23%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.52%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.98%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.80%	93.03%
CHEMBL2581	P07339	Cathepsin D	86.73%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.79%	97.14%
CHEMBL2996	Q05655	Protein kinase C delta	85.09%	97.79%
CHEMBL5028	O14672	ADAM10	84.83%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.68%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.58%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.95%	96.47%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.52%	98.75%
CHEMBL5255	O00206	Toll-like receptor 4	80.84%	92.50%

Plants that contains it

• Tetragonotheca ludoviciana

Cross-Links

• PubChem: 163006246
• LOTUS: LTS0013232
• wikiData: Q105184063