[(1S,2S,5S,8R,9R,10S,12R,14S)-10-hydroxy-5,9,14-trimethyl-4-oxo-3,13-dioxatetracyclo[7.5.0.02,6.012,14]tetradecan-8-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: a32fe7e1-9125-41ec-8761-3de7b29f015c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(1S,2S,5S,8R,9R,10S,12R,14S)-10-hydroxy-5,9,14-trimethyl-4-oxo-3,13-dioxatetracyclo[7.5.0.02,6.012,14]tetradecan-8-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H28O6/c1-6-9(2)17(22)24-13-7-11-10(3)18(23)25-15(11)16-19(13,4)12(21)8-14-20(16,5)26-14/h6,10-16,21H,7-8H2,1-5H3/b9-6-/t10-,11?,12-,13+,14+,15-,16+,19+,20+/m0/s1
• InChI Key: JHAYXWWXUGLOHK-QGBCZBPOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 6
• 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	+	0.9865	98.65%
Caco-2	+	0.5794	57.94%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6345	63.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8918	89.18%
OATP1B3 inhibitior	+	0.8875	88.75%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8027	80.27%
P-glycoprotein inhibitior	-	0.5870	58.70%
P-glycoprotein substrate	-	0.5739	57.39%
CYP3A4 substrate	+	0.6660	66.60%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8991	89.91%
CYP3A4 inhibition	-	0.6072	60.72%
CYP2C9 inhibition	-	0.8588	85.88%
CYP2C19 inhibition	-	0.8604	86.04%
CYP2D6 inhibition	-	0.9478	94.78%
CYP1A2 inhibition	-	0.8048	80.48%
CYP2C8 inhibition	-	0.7948	79.48%
CYP inhibitory promiscuity	-	0.8617	86.17%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4498	44.98%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9644	96.44%
Skin irritation	-	0.5637	56.37%
Skin corrosion	-	0.8941	89.41%
Ames mutagenesis	-	0.5082	50.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.3675	36.75%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7444	74.44%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6370	63.70%
Acute Oral Toxicity (c)	I	0.3719	37.19%
Estrogen receptor binding	+	0.8495	84.95%
Androgen receptor binding	+	0.5565	55.65%
Thyroid receptor binding	+	0.5507	55.07%
Glucocorticoid receptor binding	+	0.6501	65.01%
Aromatase binding	+	0.5311	53.11%
PPAR gamma	+	0.5553	55.53%
Honey bee toxicity	-	0.6282	62.82%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9755	97.55%

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	96.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.22%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.80%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.25%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	88.45%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.59%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.40%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.84%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.53%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.85%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.81%	96.61%

Plants that contains it

• Pluchea dioscoridis

Cross-Links

• PubChem: 162816874
• LOTUS: LTS0182607
• wikiData: Q105127839