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

Details

• Internal ID: 9bb40d9f-dbf3-4437-98cb-f205754807e8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1R,2R,6S,8E,11S)-8-methyl-3-methylidene-4,13-dioxo-5,14-dioxatricyclo[10.2.1.02,6]pentadeca-8,12(15)-dien-11-yl] acetate
• SMILES (Canonical): CC1=CCC(C2=CC(C3C(C1)OC(=O)C3=C)OC2=O)OC(=O)C
• SMILES (Isomeric): C/C/1=C\C[C@@H](C2=C[C@H]([C@H]3[C@H](C1)OC(=O)C3=C)OC2=O)OC(=O)C
• InChI: InChI=1S/C17H18O6/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/h4,7,12-15H,2,5-6H2,1,3H3/b8-4+/t12-,13-,14+,15+/m0/s1
• InChI Key: MTAWFKXRSLGICW-ZMQHVDFUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.32 g/mol
• Exact Mass: 318.11033829 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.61
• 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	+	0.9928	99.28%
Caco-2	+	0.6243	62.43%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6063	60.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9166	91.66%
OATP1B3 inhibitior	+	0.8633	86.33%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6026	60.26%
P-glycoprotein inhibitior	-	0.6907	69.07%
P-glycoprotein substrate	-	0.7859	78.59%
CYP3A4 substrate	+	0.5909	59.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9025	90.25%
CYP3A4 inhibition	-	0.5996	59.96%
CYP2C9 inhibition	-	0.8471	84.71%
CYP2C19 inhibition	-	0.8378	83.78%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.6692	66.92%
CYP inhibitory promiscuity	-	0.8519	85.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5241	52.41%
Eye corrosion	-	0.9394	93.94%
Eye irritation	-	0.6503	65.03%
Skin irritation	-	0.6036	60.36%
Skin corrosion	-	0.8982	89.82%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5844	58.44%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.7441	74.41%
skin sensitisation	-	0.6943	69.43%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7938	79.38%
Acute Oral Toxicity (c)	III	0.4588	45.88%
Estrogen receptor binding	+	0.7154	71.54%
Androgen receptor binding	-	0.5951	59.51%
Thyroid receptor binding	-	0.6854	68.54%
Glucocorticoid receptor binding	+	0.8003	80.03%
Aromatase binding	-	0.5753	57.53%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7029	70.29%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9930	99.30%

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	94.76%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.54%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.51%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.16%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.54%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.94%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.85%	99.23%
CHEMBL2581	P07339	Cathepsin D	84.41%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.40%	95.56%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.77%	96.00%

Plants that contains it

• Mikania cynanchifolia

Cross-Links

• PubChem: 162975597
• LOTUS: LTS0062200
• wikiData: Q105171586