[(1R,2R,6S,7R,9R,10S,11R,12R,14S)-7-[(E)-2-(acetyloxymethyl)but-2-enoyl]oxy-14-methyl-5-methylidene-4-oxospiro[3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradecane-9,2'-oxirane]-11-yl] (E)-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 24124bc1-29d9-4017-9eb0-baa5ec8b7fc2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: [(1R,2R,6S,7R,9R,10S,11R,12R,14S)-7-[(E)-2-(acetyloxymethyl)but-2-enoyl]oxy-14-methyl-5-methylidene-4-oxospiro[3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradecane-9,2'-oxirane]-11-yl] (E)-2-(hydroxymethyl)but-2-enoate
• InChI: InChI=1S/C27H32O11/c1-6-14(9-28)24(31)37-21-19-18(26(5)22(21)38-26)20-17(12(3)23(30)36-20)16(8-27(19)11-34-27)35-25(32)15(7-2)10-33-13(4)29/h6-7,16-22,28H,3,8-11H2,1-2,4-5H3/b14-6+,15-7+/t16-,17+,18-,19+,20-,21-,22-,26+,27+/m1/s1
• InChI Key: WBOPBWDHSKAJTA-QISITBFHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₁
• Molecular Weight: 532.50 g/mol
• Exact Mass: 532.19446183 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9365	93.65%
Caco-2	-	0.7880	78.80%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7084	70.84%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.8560	85.60%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9105	91.05%
P-glycoprotein inhibitior	+	0.7692	76.92%
P-glycoprotein substrate	+	0.5992	59.92%
CYP3A4 substrate	+	0.6695	66.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8948	89.48%
CYP3A4 inhibition	-	0.6953	69.53%
CYP2C9 inhibition	-	0.9193	91.93%
CYP2C19 inhibition	-	0.8623	86.23%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.8654	86.54%
CYP2C8 inhibition	-	0.5893	58.93%
CYP inhibitory promiscuity	-	0.9094	90.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6258	62.58%
Eye corrosion	-	0.9773	97.73%
Eye irritation	-	0.8953	89.53%
Skin irritation	-	0.6655	66.55%
Skin corrosion	-	0.9094	90.94%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7122	71.22%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	+	0.6218	62.18%
skin sensitisation	-	0.7153	71.53%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8698	86.98%
Acute Oral Toxicity (c)	III	0.3586	35.86%
Estrogen receptor binding	+	0.7043	70.43%
Androgen receptor binding	+	0.7083	70.83%
Thyroid receptor binding	+	0.5431	54.31%
Glucocorticoid receptor binding	+	0.7648	76.48%
Aromatase binding	+	0.6129	61.29%
PPAR gamma	+	0.6797	67.97%
Honey bee toxicity	-	0.5799	57.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9243	92.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.06%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.32%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.87%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.71%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.44%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.93%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	88.53%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.02%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.74%	89.34%
CHEMBL221	P23219	Cyclooxygenase-1	87.65%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.78%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.46%	97.28%
CHEMBL1951	P21397	Monoamine oxidase A	85.07%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	84.27%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.19%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.30%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.97%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.61%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.67%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.10%	94.00%

Plants that contains it

• Liatris pycnostachya

Cross-Links

• PubChem: 162905622
• LOTUS: LTS0141506
• wikiData: Q105300873