[(3aS,4R,6R,7S,10E,11aS)-7-methoxy-6,10-dimethyl-3-methylidene-2,5-dioxo-4,6,7,8,9,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 4faa3889-1f5e-41d9-bac5-d3d567d8c26d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4R,6R,7S,10E,11aS)-7-methoxy-6,10-dimethyl-3-methylidene-2,5-dioxo-4,6,7,8,9,11a-hexahydro-3aH-cyclodeca[b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(CCC(=CC2C(C(C1=O)OC(=O)C3(C(O3)C)C)C(=C)C(=O)O2)C)OC
• SMILES (Isomeric): C[C@@H]1[C@H](CC/C(=C/[C@H]2[C@@H]([C@H](C1=O)OC(=O)[C@]3([C@H](O3)C)C)C(=C)C(=O)O2)/C)OC
• InChI: InChI=1S/C21H28O7/c1-10-7-8-14(25-6)11(2)17(22)18(27-20(24)21(5)13(4)28-21)16-12(3)19(23)26-15(16)9-10/h9,11,13-16,18H,3,7-8H2,1-2,4-6H3/b10-9+/t11-,13-,14+,15+,16+,18-,21-/m1/s1
• InChI Key: JVPXFGCRXBYZOY-RBALFDDQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₇
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.18350323 g/mol
• Topological Polar Surface Area (TPSA): 91.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9788	97.88%
Caco-2	+	0.5499	54.99%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5435	54.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8664	86.64%
OATP1B3 inhibitior	+	0.9363	93.63%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5661	56.61%
P-glycoprotein inhibitior	+	0.7017	70.17%
P-glycoprotein substrate	-	0.6529	65.29%
CYP3A4 substrate	+	0.6878	68.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8848	88.48%
CYP3A4 inhibition	-	0.5788	57.88%
CYP2C9 inhibition	-	0.8735	87.35%
CYP2C19 inhibition	-	0.8618	86.18%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	+	0.5496	54.96%
CYP2C8 inhibition	-	0.5719	57.19%
CYP inhibitory promiscuity	-	0.9232	92.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4795	47.95%
Eye corrosion	-	0.9745	97.45%
Eye irritation	-	0.8642	86.42%
Skin irritation	-	0.6069	60.69%
Skin corrosion	-	0.8395	83.95%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5772	57.72%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7316	73.16%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4897	48.97%
Estrogen receptor binding	+	0.8475	84.75%
Androgen receptor binding	+	0.6459	64.59%
Thyroid receptor binding	+	0.6274	62.74%
Glucocorticoid receptor binding	+	0.8058	80.58%
Aromatase binding	+	0.6638	66.38%
PPAR gamma	+	0.7405	74.05%
Honey bee toxicity	-	0.7400	74.00%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9189	91.89%

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	98.16%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.08%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.63%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.40%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.08%	97.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.68%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.13%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.09%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.81%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.48%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.64%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.55%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.01%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.57%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.36%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.71%	89.00%
CHEMBL5028	O14672	ADAM10	80.71%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.68%	94.00%

Plants that contains it

• Montanoa hibiscifolia

Cross-Links

• PubChem: 21577299
• LOTUS: LTS0168949
• wikiData: Q105135891