[(3aS,4R,5E,9R,10E,11aS)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate

Details

• Internal ID: 557e078f-3e12-42b5-a4a8-a82688156baa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4R,5E,9R,10E,11aS)-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate
• SMILES (Canonical): CC1=CC(C2C(C=C(C(CC1)O)C)OC(=O)C2=C)OC(=O)C
• SMILES (Isomeric): C/C/1=C\[C@H]([C@H]2[C@H](/C=C(/[C@@H](CC1)O)\C)OC(=O)C2=C)OC(=O)C
• InChI: InChI=1S/C17H22O5/c1-9-5-6-13(19)10(2)8-15-16(11(3)17(20)22-15)14(7-9)21-12(4)18/h7-8,13-16,19H,3,5-6H2,1-2,4H3/b9-7+,10-8+/t13-,14-,15+,16+/m1/s1
• InChI Key: QAUJITGGHQZVFF-UCEZPBCSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 2.06
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.7466	74.66%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5894	58.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.8767	87.67%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9042	90.42%
P-glycoprotein inhibitior	-	0.8360	83.60%
P-glycoprotein substrate	-	0.8653	86.53%
CYP3A4 substrate	+	0.5840	58.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.6136	61.36%
CYP2C9 inhibition	-	0.8841	88.41%
CYP2C19 inhibition	-	0.8843	88.43%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.7802	78.02%
CYP inhibitory promiscuity	-	0.9589	95.89%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5967	59.67%
Eye corrosion	-	0.9655	96.55%
Eye irritation	-	0.6482	64.82%
Skin irritation	-	0.5246	52.46%
Skin corrosion	-	0.8640	86.40%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6460	64.60%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6416	64.16%
skin sensitisation	-	0.7696	76.96%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5480	54.80%
Acute Oral Toxicity (c)	III	0.3760	37.60%
Estrogen receptor binding	-	0.4923	49.23%
Androgen receptor binding	-	0.6447	64.47%
Thyroid receptor binding	-	0.5911	59.11%
Glucocorticoid receptor binding	+	0.6469	64.69%
Aromatase binding	-	0.7036	70.36%
PPAR gamma	-	0.5976	59.76%
Honey bee toxicity	-	0.7790	77.90%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9512	95.12%

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	90.35%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.01%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.64%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.54%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.66%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.48%	94.45%
CHEMBL2581	P07339	Cathepsin D	84.36%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.61%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.62%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.47%	95.89%

Plants that contains it

• Tanacetum densum

Cross-Links

• PubChem: 163025918
• LOTUS: LTS0266264
• wikiData: Q105217624