methyl (1R,2E,4S,6R,7E,9S,10S,11R)-10-[(2S,3S)-3-acetyloxy-2-hydroxy-2-methylbutanoyl]oxy-3-methyl-9-[(2R)-2-methylbutanoyl]oxy-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate

Details

• Internal ID: 6c874692-c8a1-4e94-806d-3350acbf1e75
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl (1R,2E,4S,6R,7E,9S,10S,11R)-10-[(2S,3S)-3-acetyloxy-2-hydroxy-2-methylbutanoyl]oxy-3-methyl-9-[(2R)-2-methylbutanoyl]oxy-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.04,6]tetradeca-2,7-diene-8-carboxylate
• InChI: InChI=1S/C28H36O12/c1-9-12(2)24(30)39-22-17(26(32)35-8)11-19-21(37-19)13(3)10-18-20(14(4)25(31)38-18)23(22)40-27(33)28(7,34)15(5)36-16(6)29/h10-12,15,18-23,34H,4,9H2,1-3,5-8H3/b13-10+,17-11+/t12-,15+,18-,19-,20-,21+,22+,23+,28+/m1/s1
• InChI Key: PGGJXRNXCXSEIB-OSVVSDBISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₂
• Molecular Weight: 564.60 g/mol
• Exact Mass: 564.22067658 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 12
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9765	97.65%
Caco-2	-	0.7781	77.81%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5293	52.93%
OATP2B1 inhibitior	-	0.7210	72.10%
OATP1B1 inhibitior	+	0.7931	79.31%
OATP1B3 inhibitior	+	0.8981	89.81%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8142	81.42%
P-glycoprotein inhibitior	+	0.8380	83.80%
P-glycoprotein substrate	+	0.6008	60.08%
CYP3A4 substrate	+	0.6822	68.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9053	90.53%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8159	81.59%
CYP2C19 inhibition	-	0.7863	78.63%
CYP2D6 inhibition	-	0.9241	92.41%
CYP1A2 inhibition	-	0.7855	78.55%
CYP2C8 inhibition	+	0.6726	67.26%
CYP inhibitory promiscuity	-	0.8432	84.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Danger	0.4196	41.96%
Eye corrosion	-	0.9665	96.65%
Eye irritation	-	0.8961	89.61%
Skin irritation	-	0.6764	67.64%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5708	57.08%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5336	53.36%
skin sensitisation	-	0.6424	64.24%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5751	57.51%
Acute Oral Toxicity (c)	III	0.4596	45.96%
Estrogen receptor binding	+	0.7793	77.93%
Androgen receptor binding	+	0.6377	63.77%
Thyroid receptor binding	+	0.5910	59.10%
Glucocorticoid receptor binding	+	0.8096	80.96%
Aromatase binding	+	0.5836	58.36%
PPAR gamma	+	0.7021	70.21%
Honey bee toxicity	-	0.7234	72.34%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9471	94.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	97.83%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.96%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.39%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.74%	85.14%
CHEMBL2581	P07339	Cathepsin D	89.61%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.30%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.09%	97.21%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.00%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.65%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.33%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.56%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.50%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	82.86%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.69%	97.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.30%	98.75%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.03%	96.90%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.93%	90.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.11%	94.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.84%	96.47%

Plants that contains it

• Melampodium americanum

Cross-Links

• PubChem: 163087516
• LOTUS: LTS0018836
• wikiData: Q105208379