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

Details

• Internal ID: bac14312-a037-4abb-81aa-667c79fe882a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3R,3aS,6Z,9S,10Z,11aS)-3,6,10-trimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-9-yl] acetate
• SMILES (Canonical): CC1C2CCC(=CCC(C(=CC2OC1=O)C)OC(=O)C)C
• SMILES (Isomeric): C[C@@H]1[C@@H]2CC/C(=C\C[C@@H](/C(=C\[C@H]2OC1=O)/C)OC(=O)C)/C
• InChI: InChI=1S/C17H24O4/c1-10-5-7-14-12(3)17(19)21-16(14)9-11(2)15(8-6-10)20-13(4)18/h6,9,12,14-16H,5,7-8H2,1-4H3/b10-6-,11-9-/t12-,14+,15+,16-/m1/s1
• InChI Key: GYXQQENGZKKHNQ-ISVRTBQUSA-N
• Popularity: 1 reference 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: 2.40
• 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	+	0.9921	99.21%
Caco-2	+	0.8252	82.52%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6672	66.72%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9194	91.94%
OATP1B3 inhibitior	+	0.9199	91.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5816	58.16%
P-glycoprotein inhibitior	-	0.6274	62.74%
P-glycoprotein substrate	-	0.7878	78.78%
CYP3A4 substrate	+	0.6028	60.28%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8605	86.05%
CYP3A4 inhibition	-	0.7383	73.83%
CYP2C9 inhibition	-	0.9025	90.25%
CYP2C19 inhibition	-	0.8178	81.78%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	+	0.6318	63.18%
CYP2C8 inhibition	-	0.8051	80.51%
CYP inhibitory promiscuity	-	0.8958	89.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6611	66.11%
Eye corrosion	-	0.9593	95.93%
Eye irritation	-	0.9001	90.01%
Skin irritation	-	0.5511	55.11%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4334	43.34%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.7647	76.47%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5117	51.17%
Acute Oral Toxicity (c)	III	0.5403	54.03%
Estrogen receptor binding	-	0.5861	58.61%
Androgen receptor binding	-	0.5824	58.24%
Thyroid receptor binding	-	0.6800	68.00%
Glucocorticoid receptor binding	+	0.5542	55.42%
Aromatase binding	-	0.8115	81.15%
PPAR gamma	-	0.6173	61.73%
Honey bee toxicity	-	0.8023	80.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9902	99.02%

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	96.18%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.30%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.21%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.73%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.56%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.97%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.82%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.28%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.39%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.02%	99.23%

Plants that contains it

• Ajania fruticulosa

Cross-Links

• PubChem: 100931476
• LOTUS: LTS0209072
• wikiData: Q105024224