Methyl 5-acetyloxy-4-(2,3-dimethyloxirane-2-carbonyl)oxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carboxylate

Details

• Internal ID: 68a18ef2-5436-42f5-940b-79fbfb9485a0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl 5-acetyloxy-4-(2,3-dimethyloxirane-2-carbonyl)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(=O)OC)C)OC(=O)C3=C
• SMILES (Isomeric): CC1C(O1)(C)C(=O)OC2C3C(C=C(CCC=C(C2OC(=O)C)C(=O)OC)C)OC(=O)C3=C
• InChI: InChI=1S/C23H28O9/c1-11-8-7-9-15(21(26)28-6)18(29-14(4)24)19(31-22(27)23(5)13(3)32-23)17-12(2)20(25)30-16(17)10-11/h9-10,13,16-19H,2,7-8H2,1,3-6H3
• InChI Key: JIEVJXRUYDZFTD-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₉
• Molecular Weight: 448.50 g/mol
• Exact Mass: 448.17333247 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.94
• H-Bond Acceptor: 9
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• CID 92043370

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9819	98.19%
Caco-2	+	0.5173	51.73%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5304	53.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8523	85.23%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7809	78.09%
P-glycoprotein inhibitior	+	0.8234	82.34%
P-glycoprotein substrate	-	0.5405	54.05%
CYP3A4 substrate	+	0.6834	68.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9019	90.19%
CYP3A4 inhibition	-	0.6424	64.24%
CYP2C9 inhibition	-	0.8654	86.54%
CYP2C19 inhibition	-	0.8346	83.46%
CYP2D6 inhibition	-	0.9159	91.59%
CYP1A2 inhibition	+	0.5330	53.30%
CYP2C8 inhibition	+	0.5177	51.77%
CYP inhibitory promiscuity	-	0.8765	87.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4748	47.48%
Eye corrosion	-	0.9645	96.45%
Eye irritation	-	0.8801	88.01%
Skin irritation	-	0.6432	64.32%
Skin corrosion	-	0.8871	88.71%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6763	67.63%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5940	59.40%
skin sensitisation	-	0.6977	69.77%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5896	58.96%
Acute Oral Toxicity (c)	III	0.4500	45.00%
Estrogen receptor binding	+	0.7771	77.71%
Androgen receptor binding	+	0.5977	59.77%
Thyroid receptor binding	+	0.6197	61.97%
Glucocorticoid receptor binding	+	0.8673	86.73%
Aromatase binding	+	0.5787	57.87%
PPAR gamma	+	0.8024	80.24%
Honey bee toxicity	-	0.6851	68.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9562	95.62%

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	99.06%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.70%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.61%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.33%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.19%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.11%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.33%	93.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.22%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.97%	97.14%
CHEMBL2581	P07339	Cathepsin D	85.96%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	85.43%	97.79%
CHEMBL5028	O14672	ADAM10	84.15%	97.50%
CHEMBL4208	P20618	Proteasome component C5	82.99%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.66%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	82.63%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.08%	97.25%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.83%	81.11%
CHEMBL5255	O00206	Toll-like receptor 4	81.44%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.79%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.51%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.50%	95.89%

Plants that contains it

• Enydra fluctuans
• Smallanthus fruticosus
• Smallanthus sonchifolius
• Smallanthus uvedalia

Cross-Links

• PubChem: 74155557
• LOTUS: LTS0248567
• wikiData: Q104169562