[(3aR,4R,6E,9R,10Z,11aS)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-[[(E)-2-methylbut-2-enoyl]oxymethyl]but-2-enoate

Details

• Internal ID: 6332dcf6-32f5-4053-bd34-a32feeba818d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6E,9R,10Z,11aS)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-[[(E)-2-methylbut-2-enoyl]oxymethyl]but-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OCC(=CCO)C(=O)OC1CC(=CCC(C(=CC2C1C(=C)C(=O)O2)C)OC(=O)C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)OC/C(=C\CO)/C(=O)O[C@@H]1C/C(=C/C[C@H](/C(=C\[C@H]2[C@@H]1C(=C)C(=O)O2)/C)OC(=O)C)/C
• InChI: InChI=1S/C27H34O9/c1-7-16(3)25(30)33-14-20(10-11-28)27(32)36-22-12-15(2)8-9-21(34-19(6)29)17(4)13-23-24(22)18(5)26(31)35-23/h7-8,10,13,21-24,28H,5,9,11-12,14H2,1-4,6H3/b15-8+,16-7+,17-13-,20-10+/t21-,22-,23+,24-/m1/s1
• InChI Key: SBQXXQCXZGLVOZ-QLYNAZOXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₉
• Molecular Weight: 502.60 g/mol
• Exact Mass: 502.22028266 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.04
• 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	+	0.9578	95.78%
Caco-2	-	0.7762	77.62%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6172	61.72%
OATP2B1 inhibitior	-	0.7154	71.54%
OATP1B1 inhibitior	+	0.8580	85.80%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9235	92.35%
P-glycoprotein inhibitior	+	0.8643	86.43%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6673	66.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.5566	55.66%
CYP2C9 inhibition	-	0.8330	83.30%
CYP2C19 inhibition	-	0.7753	77.53%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.6099	60.99%
CYP2C8 inhibition	+	0.5278	52.78%
CYP inhibitory promiscuity	-	0.8521	85.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6036	60.36%
Eye corrosion	-	0.9725	97.25%
Eye irritation	-	0.9231	92.31%
Skin irritation	-	0.6062	60.62%
Skin corrosion	-	0.9348	93.48%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6801	68.01%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8057	80.57%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.8191	81.91%
Acute Oral Toxicity (c)	III	0.4934	49.34%
Estrogen receptor binding	+	0.8125	81.25%
Androgen receptor binding	+	0.5451	54.51%
Thyroid receptor binding	+	0.5344	53.44%
Glucocorticoid receptor binding	+	0.7879	78.79%
Aromatase binding	+	0.5795	57.95%
PPAR gamma	+	0.5859	58.59%
Honey bee toxicity	-	0.6515	65.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9766	97.66%

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	97.84%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.35%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.84%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.65%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.80%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.45%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.17%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.55%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.67%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.24%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.90%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.33%	94.80%
CHEMBL221	P23219	Cyclooxygenase-1	82.15%	90.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.53%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.36%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.23%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.21%	93.00%

Plants that contains it

• Ageratina palmeri

Cross-Links

• PubChem: 163001281
• LOTUS: LTS0233746
• wikiData: Q105249625