[(1R,2R,3R,6S,8E,11S)-3,8-dimethyl-4,13-dioxo-5,14-dioxatricyclo[10.2.1.02,6]pentadeca-8,12(15)-dien-11-yl] acetate

Details

• Internal ID: 3b5ce87f-90c9-4641-b8be-a1c1e221dc9a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1R,2R,3R,6S,8E,11S)-3,8-dimethyl-4,13-dioxo-5,14-dioxatricyclo[10.2.1.02,6]pentadeca-8,12(15)-dien-11-yl] acetate
• SMILES (Canonical): CC1C2C(CC(=CCC(C3=CC2OC3=O)OC(=O)C)C)OC1=O
• SMILES (Isomeric): C[C@@H]1[C@@H]2[C@H](C/C(=C/C[C@@H](C3=C[C@H]2OC3=O)OC(=O)C)/C)OC1=O
• InChI: InChI=1S/C17H20O6/c1-8-4-5-12(21-10(3)18)11-7-14(23-17(11)20)15-9(2)16(19)22-13(15)6-8/h4,7,9,12-15H,5-6H2,1-3H3/b8-4+/t9-,12+,13+,14-,15-/m1/s1
• InChI Key: MBSONWVPLADQOL-XPEONNQGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.12598835 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.69
• H-Bond Acceptor: 6
• 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	+	0.9942	99.42%
Caco-2	+	0.7294	72.94%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6307	63.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9073	90.73%
OATP1B3 inhibitior	+	0.9011	90.11%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5539	55.39%
P-glycoprotein inhibitior	-	0.6873	68.73%
P-glycoprotein substrate	-	0.7283	72.83%
CYP3A4 substrate	+	0.6069	60.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9025	90.25%
CYP3A4 inhibition	-	0.6660	66.60%
CYP2C9 inhibition	-	0.8560	85.60%
CYP2C19 inhibition	-	0.8751	87.51%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.5522	55.22%
CYP2C8 inhibition	-	0.7770	77.70%
CYP inhibitory promiscuity	-	0.8693	86.93%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4543	45.43%
Eye corrosion	-	0.9477	94.77%
Eye irritation	-	0.7973	79.73%
Skin irritation	-	0.6104	61.04%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5697	56.97%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.8191	81.91%
skin sensitisation	-	0.7608	76.08%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7588	75.88%
Acute Oral Toxicity (c)	III	0.4961	49.61%
Estrogen receptor binding	+	0.6971	69.71%
Androgen receptor binding	-	0.5912	59.12%
Thyroid receptor binding	-	0.6404	64.04%
Glucocorticoid receptor binding	+	0.7763	77.63%
Aromatase binding	-	0.6880	68.80%
PPAR gamma	-	0.5261	52.61%
Honey bee toxicity	-	0.8060	80.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9848	98.48%

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	94.28%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.82%	94.80%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.56%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.53%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.28%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.12%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.32%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.15%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.82%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.20%	85.14%

Plants that contains it

• Mikania cynanchifolia
• Mikania periplocifolia

Cross-Links

• PubChem: 163022300
• LOTUS: LTS0093689
• wikiData: Q105160942