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

Details

• Internal ID: 400e9971-b305-4990-9a3f-8ad97bd681e2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(1S,2R,4S,5R,9S,10S,11R)-2-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.01,10.05,9]pentadec-14-en-4-yl] propanoate
• InChI: InChI=1S/C18H22O7/c1-5-11(19)22-10-8-17(4,21)18-7-6-16(3,24-25-18)14(18)13-12(10)9(2)15(20)23-13/h6-7,10,12-14,21H,2,5,8H2,1,3-4H3/t10-,12+,13-,14-,16+,17+,18-/m0/s1
• InChI Key: JUGXZNIBVYVWTE-VHYAJVQDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₇
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.13655304 g/mol
• Topological Polar Surface Area (TPSA): 91.30 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.21
• H-Bond Acceptor: 7
• 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	+	0.9764	97.64%
Caco-2	-	0.5289	52.89%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5100	51.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.8682	86.82%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8953	89.53%
P-glycoprotein inhibitior	-	0.6083	60.83%
P-glycoprotein substrate	-	0.6481	64.81%
CYP3A4 substrate	+	0.6411	64.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8861	88.61%
CYP3A4 inhibition	+	0.6002	60.02%
CYP2C9 inhibition	-	0.8655	86.55%
CYP2C19 inhibition	-	0.8118	81.18%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.8502	85.02%
CYP2C8 inhibition	-	0.5805	58.05%
CYP inhibitory promiscuity	-	0.9271	92.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5282	52.82%
Eye corrosion	-	0.9765	97.65%
Eye irritation	-	0.9311	93.11%
Skin irritation	-	0.6431	64.31%
Skin corrosion	-	0.9117	91.17%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4696	46.96%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7328	73.28%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5455	54.55%
Acute Oral Toxicity (c)	III	0.4414	44.14%
Estrogen receptor binding	+	0.7903	79.03%
Androgen receptor binding	+	0.6605	66.05%
Thyroid receptor binding	+	0.7324	73.24%
Glucocorticoid receptor binding	+	0.7566	75.66%
Aromatase binding	+	0.6041	60.41%
PPAR gamma	+	0.6368	63.68%
Honey bee toxicity	-	0.8321	83.21%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5850	58.50%
Fish aquatic toxicity	+	0.9660	96.60%

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	97.44%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.19%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.36%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.19%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.29%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.39%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.36%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	84.96%	97.79%
CHEMBL2581	P07339	Cathepsin D	84.33%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.57%	97.09%
CHEMBL4208	P20618	Proteasome component C5	82.89%	90.00%

Plants that contains it

• Artemisia douglasiana

Cross-Links

• PubChem: 162856171
• LOTUS: LTS0148645
• wikiData: Q105135235