[(E)-4-[[(1S,2S,4S,7E,10R,11R)-4-(hydroxymethyl)-8-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-10-yl]oxy]-3-methyl-4-oxobut-2-enyl] (3R)-3-hydroxyoctadecanoate

Details

• Internal ID: b2d59b4c-63f8-4a85-aa8e-9911398f8858
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(E)-4-[[(1S,2S,4S,7E,10R,11R)-4-(hydroxymethyl)-8-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-10-yl]oxy]-3-methyl-4-oxobut-2-enyl] (3R)-3-hydroxyoctadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(CC(=O)OCC=C(C)C(=O)OC1CC(=CCCC2(C(O2)C3C1C(=C)C(=O)O3)CO)C)O
• SMILES (Isomeric): CCCCCCCCCCCCCCC[C@H](CC(=O)OC/C=C(\C)/C(=O)O[C@@H]1C/C(=C/CC[C@@]2([C@@H](O2)[C@@H]3[C@@H]1C(=C)C(=O)O3)CO)/C)O
• InChI: InChI=1S/C38H60O9/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-30(40)25-32(41)44-23-21-28(3)36(42)45-31-24-27(2)19-18-22-38(26-39)35(47-38)34-33(31)29(4)37(43)46-34/h19,21,30-31,33-35,39-40H,4-18,20,22-26H2,1-3H3/b27-19+,28-21+/t30-,31-,33-,34+,35+,38+/m1/s1
• InChI Key: MVHKLUNQRGAKNA-MFYILHFSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₀O₉
• Molecular Weight: 660.90 g/mol
• Exact Mass: 660.42373349 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 8.50
• Atomic LogP (AlogP): 6.98
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 21

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9608	96.08%
Caco-2	-	0.8247	82.47%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6747	67.47%
OATP2B1 inhibitior	-	0.5742	57.42%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9408	94.08%
P-glycoprotein inhibitior	+	0.7446	74.46%
P-glycoprotein substrate	+	0.6595	65.95%
CYP3A4 substrate	+	0.7058	70.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8957	89.57%
CYP3A4 inhibition	+	0.7298	72.98%
CYP2C9 inhibition	-	0.6703	67.03%
CYP2C19 inhibition	-	0.8068	80.68%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.7670	76.70%
CYP2C8 inhibition	+	0.6788	67.88%
CYP inhibitory promiscuity	-	0.9216	92.16%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4520	45.20%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9015	90.15%
Skin irritation	+	0.5060	50.60%
Skin corrosion	-	0.9326	93.26%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3697	36.97%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8649	86.49%
Acute Oral Toxicity (c)	III	0.4920	49.20%
Estrogen receptor binding	+	0.7826	78.26%
Androgen receptor binding	+	0.7163	71.63%
Thyroid receptor binding	-	0.5712	57.12%
Glucocorticoid receptor binding	+	0.6236	62.36%
Aromatase binding	+	0.5707	57.07%
PPAR gamma	+	0.5607	56.07%
Honey bee toxicity	-	0.7153	71.53%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5702	57.02%
Fish aquatic toxicity	+	0.9754	97.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.44%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL299	P17252	Protein kinase C alpha	97.80%	98.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.36%	94.45%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	96.69%	94.08%
CHEMBL2996	Q05655	Protein kinase C delta	95.55%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	95.34%	90.17%
CHEMBL2581	P07339	Cathepsin D	95.25%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.44%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.42%	95.56%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.39%	97.29%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.28%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.05%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.63%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.95%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.15%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	88.66%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.28%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.83%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.94%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.58%	95.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.59%	96.90%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.54%	99.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.05%	96.47%
CHEMBL230	P35354	Cyclooxygenase-2	83.35%	89.63%
CHEMBL5028	O14672	ADAM10	82.79%	97.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.42%	94.62%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.76%	96.37%
CHEMBL340	P08684	Cytochrome P450 3A4	81.51%	91.19%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	81.50%	91.81%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	80.82%	97.50%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.51%	85.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.40%	95.89%

Plants that contains it

• Eupatorium hyssopifolium

Cross-Links

• PubChem: 163053493
• LOTUS: LTS0273731
• wikiData: Q105173020