[(1S,2S,4S,5R,9S,10S,11R)-2-hydroperoxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.01,10.05,9]pentadec-14-en-4-yl] acetate

Details

• Internal ID: 61731d78-9076-42f3-ab30-c061a09a22ca
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(1S,2S,4S,5R,9S,10S,11R)-2-hydroperoxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.01,10.05,9]pentadec-14-en-4-yl] acetate
• InChI: InChI=1S/C17H20O8/c1-8-11-10(21-9(2)18)7-16(4,23-20)17-6-5-15(3,24-25-17)13(17)12(11)22-14(8)19/h5-6,10-13,20H,1,7H2,2-4H3/t10-,11+,12-,13-,15+,16-,17-/m0/s1
• InChI Key: KKSBOIOUPUSWLD-DIQVCCITSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₈
• Molecular Weight: 352.30 g/mol
• Exact Mass: 352.11581759 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9401	94.01%
Caco-2	-	0.5740	57.40%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6233	62.33%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.8528	85.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7782	77.82%
P-glycoprotein inhibitior	-	0.6561	65.61%
P-glycoprotein substrate	-	0.7259	72.59%
CYP3A4 substrate	+	0.6461	64.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8765	87.65%
CYP3A4 inhibition	+	0.5179	51.79%
CYP2C9 inhibition	-	0.8372	83.72%
CYP2C19 inhibition	-	0.8080	80.80%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.7584	75.84%
CYP2C8 inhibition	-	0.6646	66.46%
CYP inhibitory promiscuity	-	0.9267	92.67%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.4948	49.48%
Eye corrosion	-	0.9697	96.97%
Eye irritation	-	0.8902	89.02%
Skin irritation	-	0.6877	68.77%
Skin corrosion	-	0.8793	87.93%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4435	44.35%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.7613	76.13%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7980	79.80%
Acute Oral Toxicity (c)	III	0.4289	42.89%
Estrogen receptor binding	+	0.8315	83.15%
Androgen receptor binding	+	0.7045	70.45%
Thyroid receptor binding	+	0.7473	74.73%
Glucocorticoid receptor binding	+	0.7008	70.08%
Aromatase binding	-	0.5582	55.82%
PPAR gamma	+	0.7152	71.52%
Honey bee toxicity	-	0.7278	72.78%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9531	95.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.07%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.93%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.34%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.96%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.15%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.94%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.83%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.18%	95.56%
CHEMBL2581	P07339	Cathepsin D	82.10%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.22%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	80.30%	97.79%

Plants that contains it

• Artemisia afra

Cross-Links

• PubChem: 163036646
• LOTUS: LTS0141820
• wikiData: Q105142334