[(3aR,5S,11aS)-3,6,10-trimethylidene-2,9-dioxo-4,5,7,8,11,11a-hexahydro-3aH-cyclodeca[b]furan-5-yl] acetate

Details

• Internal ID: 681ef81c-8bf1-4ad8-939d-52db5bfafa82
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3aR,5S,11aS)-3,6,10-trimethylidene-2,9-dioxo-4,5,7,8,11,11a-hexahydro-3aH-cyclodeca[b]furan-5-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(CC(=C)C(=O)CCC1=C)OC(=O)C2=C
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@H]2[C@H](CC(=C)C(=O)CCC1=C)OC(=O)C2=C
• InChI: InChI=1S/C17H20O5/c1-9-5-6-14(19)10(2)7-16-13(11(3)17(20)22-16)8-15(9)21-12(4)18/h13,15-16H,1-3,5-8H2,4H3/t13-,15+,16+/m1/s1
• InChI Key: RPWHOULKLRDDNC-KBMXLJTQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.34 g/mol
• Exact Mass: 304.13107373 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.27
• H-Bond Acceptor: 5
• 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	+	0.9885	98.85%
Caco-2	+	0.4917	49.17%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7283	72.83%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8891	88.91%
OATP1B3 inhibitior	+	0.9228	92.28%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.9062	90.62%
P-glycoprotein inhibitior	-	0.7442	74.42%
P-glycoprotein substrate	-	0.8276	82.76%
CYP3A4 substrate	+	0.5727	57.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.8165	81.65%
CYP2C9 inhibition	-	0.8850	88.50%
CYP2C19 inhibition	-	0.7127	71.27%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	+	0.5724	57.24%
CYP2C8 inhibition	-	0.6931	69.31%
CYP inhibitory promiscuity	-	0.8324	83.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9568	95.68%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.8559	85.59%
Eye irritation	-	0.5127	51.27%
Skin irritation	-	0.6668	66.68%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5444	54.44%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.6392	63.92%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.8114	81.14%
Acute Oral Toxicity (c)	III	0.6025	60.25%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5541	55.41%
Thyroid receptor binding	-	0.6065	60.65%
Glucocorticoid receptor binding	+	0.7024	70.24%
Aromatase binding	-	0.7280	72.80%
PPAR gamma	-	0.5731	57.31%
Honey bee toxicity	-	0.6558	65.58%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9784	97.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.07%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.84%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.53%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.67%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.82%	99.23%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.82%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.78%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	83.33%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.99%	86.33%
CHEMBL2581	P07339	Cathepsin D	82.77%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.18%	89.00%

Plants that contains it

• Calea szyszylowiczii

Cross-Links

• PubChem: 162922058
• LOTUS: LTS0138523
• wikiData: Q105243083