Methyl 1-(chloromethyl)-2-hydroxy-8-[2-(hydroxymethyl)but-2-enoyloxy]-9-(2-methylbutanoyloxy)-6-methylidene-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradecane-10-carboxylate

Details

• Internal ID: b26b3113-4fac-47a0-bac3-c636ba1acb74
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl 1-(chloromethyl)-2-hydroxy-8-[2-(hydroxymethyl)but-2-enoyloxy]-9-(2-methylbutanoyloxy)-6-methylidene-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradecane-10-carboxylate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2CCC(O2)(C(C3C(C1OC(=O)C(=CC)CO)C(=C)C(=O)O3)O)CCl)C(=O)OC
• SMILES (Isomeric): CCC(C)C(=O)OC1C(C2CCC(O2)(C(C3C(C1OC(=O)C(=CC)CO)C(=C)C(=O)O3)O)CCl)C(=O)OC
• InChI: InChI=1S/C26H35ClO11/c1-6-12(3)22(30)35-19-17(25(33)34-5)15-8-9-26(11-27,38-15)21(29)20-16(13(4)23(31)37-20)18(19)36-24(32)14(7-2)10-28/h7,12,15-21,28-29H,4,6,8-11H2,1-3,5H3
• InChI Key: YWPYYKGRHLJLGA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₅ClO₁₁
• Molecular Weight: 559.00 g/mol
• Exact Mass: 558.1867896 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.21
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9741	97.41%
Caco-2	-	0.7511	75.11%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7196	71.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8162	81.62%
OATP1B3 inhibitior	+	0.9095	90.95%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.7212	72.12%
P-glycoprotein inhibitior	+	0.6845	68.45%
P-glycoprotein substrate	+	0.6498	64.98%
CYP3A4 substrate	+	0.6966	69.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8934	89.34%
CYP3A4 inhibition	-	0.6408	64.08%
CYP2C9 inhibition	-	0.7769	77.69%
CYP2C19 inhibition	-	0.7783	77.83%
CYP2D6 inhibition	-	0.9140	91.40%
CYP1A2 inhibition	-	0.7630	76.30%
CYP2C8 inhibition	+	0.4470	44.70%
CYP inhibitory promiscuity	-	0.9035	90.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8244	82.44%
Carcinogenicity (trinary)	Danger	0.4496	44.96%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.9194	91.94%
Skin irritation	-	0.6355	63.55%
Skin corrosion	-	0.9293	92.93%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6073	60.73%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6104	61.04%
skin sensitisation	-	0.8927	89.27%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6801	68.01%
Acute Oral Toxicity (c)	III	0.4635	46.35%
Estrogen receptor binding	+	0.7727	77.27%
Androgen receptor binding	+	0.6476	64.76%
Thyroid receptor binding	+	0.5359	53.59%
Glucocorticoid receptor binding	+	0.7506	75.06%
Aromatase binding	+	0.5986	59.86%
PPAR gamma	+	0.6665	66.65%
Honey bee toxicity	-	0.6522	65.22%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9763	97.63%

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	99.10%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.76%	91.11%
CHEMBL299	P17252	Protein kinase C alpha	96.87%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.36%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.84%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.70%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.65%	96.47%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.86%	96.61%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.91%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.21%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.06%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	88.71%	95.93%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	88.56%	92.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.51%	97.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.77%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.02%	95.89%
CHEMBL4072	P07858	Cathepsin B	86.36%	93.67%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.15%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.98%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.43%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	84.84%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.60%	91.07%
CHEMBL2581	P07339	Cathepsin D	84.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.92%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	81.68%	91.19%
CHEMBL5028	O14672	ADAM10	81.62%	97.50%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.75%	86.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.43%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.05%	93.03%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.02%	89.50%

Plants that contains it

• Tetragonotheca ludoviciana

Cross-Links

• PubChem: 162903535
• LOTUS: LTS0272116
• wikiData: Q105367037