[(3R,3aR,5Z,7S,9E,11aR)-3,6,10-trimethyl-2-oxo-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-7-yl] acetate

Details

• Internal ID: 7b89e9f6-3179-4a1c-861b-623975dfbb8e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3R,3aR,5Z,7S,9E,11aR)-3,6,10-trimethyl-2-oxo-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-7-yl] acetate
• SMILES (Canonical): CC1C2CC=C(C(CC=C(CC2OC1=O)C)OC(=O)C)C
• SMILES (Isomeric): C[C@@H]1[C@H]2C/C=C(\[C@H](C/C=C(/C[C@H]2OC1=O)\C)OC(=O)C)/C
• InChI: InChI=1S/C17H24O4/c1-10-5-8-15(20-13(4)18)11(2)6-7-14-12(3)17(19)21-16(14)9-10/h5-6,12,14-16H,7-9H2,1-4H3/b10-5+,11-6-/t12-,14-,15+,16-/m1/s1
• InChI Key: FWCGEBHNUDACCZ-XOVSNVFFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.40 g/mol
• Exact Mass: 292.16745924 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.8065	80.65%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6184	61.84%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.9387	93.87%
OATP1B3 inhibitior	+	0.9205	92.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6290	62.90%
P-glycoprotein inhibitior	-	0.6948	69.48%
P-glycoprotein substrate	-	0.7279	72.79%
CYP3A4 substrate	+	0.5598	55.98%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8605	86.05%
CYP3A4 inhibition	-	0.7735	77.35%
CYP2C9 inhibition	-	0.8977	89.77%
CYP2C19 inhibition	-	0.8385	83.85%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.5675	56.75%
CYP2C8 inhibition	-	0.8768	87.68%
CYP inhibitory promiscuity	-	0.8711	87.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9217	92.17%
Carcinogenicity (trinary)	Non-required	0.6080	60.80%
Eye corrosion	-	0.9551	95.51%
Eye irritation	-	0.8563	85.63%
Skin irritation	-	0.6168	61.68%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4218	42.18%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.8837	88.37%
skin sensitisation	-	0.6941	69.41%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7507	75.07%
Acute Oral Toxicity (c)	III	0.5203	52.03%
Estrogen receptor binding	+	0.5310	53.10%
Androgen receptor binding	-	0.6436	64.36%
Thyroid receptor binding	-	0.6815	68.15%
Glucocorticoid receptor binding	+	0.6743	67.43%
Aromatase binding	-	0.7498	74.98%
PPAR gamma	-	0.5072	50.72%
Honey bee toxicity	-	0.7373	73.73%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9937	99.37%

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	93.64%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.14%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.99%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.62%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.60%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.96%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.54%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.49%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.78%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.93%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.17%	85.14%

Plants that contains it

• Stevia yaconensis

Cross-Links

• PubChem: 15143889
• LOTUS: LTS0189433
• wikiData: Q105003095