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

Details

• Internal ID: 03ab2105-4769-45ea-b297-ffeb47e1188c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: methyl 9-butan-2-yloxy-1-(chloromethyl)-2-hydroxy-8-[2-(hydroxymethyl)but-2-enoyloxy]-6-methylidene-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradecane-10-carboxylate
• SMILES (Canonical): CCC(C)OC1C(C2CCC(O2)(C(C3C(C1OC(=O)C(=CC)CO)C(=C)C(=O)O3)O)CCl)C(=O)OC
• SMILES (Isomeric): CCC(C)OC1C(C2CCC(O2)(C(C3C(C1OC(=O)C(=CC)CO)C(=C)C(=O)O3)O)CCl)C(=O)OC
• InChI: InChI=1S/C25H35ClO10/c1-6-12(3)33-19-17(24(31)32-5)15-8-9-25(11-26,36-15)21(28)20-16(13(4)22(29)35-20)18(19)34-23(30)14(7-2)10-27/h7,12,15-21,27-28H,4,6,8-11H2,1-3,5H3
• InChI Key: CDBISUDKLFWAQY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₅ClO₁₀
• Molecular Weight: 531.00 g/mol
• Exact Mass: 530.1918750 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 10
• 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	-	0.7016	70.16%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7196	71.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8182	81.82%
OATP1B3 inhibitior	+	0.9095	90.95%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6884	68.84%
P-glycoprotein inhibitior	+	0.6469	64.69%
P-glycoprotein substrate	+	0.6724	67.24%
CYP3A4 substrate	+	0.6947	69.47%
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	-	0.5625	56.25%
CYP inhibitory promiscuity	-	0.9035	90.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8244	82.44%
Carcinogenicity (trinary)	Danger	0.4496	44.96%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.6355	63.55%
Skin corrosion	-	0.9293	92.93%
Ames mutagenesis	-	0.5940	59.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.6552	65.52%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5354	53.54%
skin sensitisation	-	0.8927	89.27%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.7192	71.92%
Acute Oral Toxicity (c)	III	0.4635	46.35%
Estrogen receptor binding	+	0.7270	72.70%
Androgen receptor binding	+	0.5795	57.95%
Thyroid receptor binding	+	0.5272	52.72%
Glucocorticoid receptor binding	+	0.7244	72.44%
Aromatase binding	+	0.6212	62.12%
PPAR gamma	+	0.6688	66.88%
Honey bee toxicity	-	0.6433	64.33%
Biodegradation	-	0.6500	65.00%
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	98.81%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.26%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.43%	96.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.77%	95.71%
CHEMBL299	P17252	Protein kinase C alpha	91.69%	98.03%
CHEMBL221	P23219	Cyclooxygenase-1	90.23%	90.17%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.14%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.13%	96.47%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	89.87%	92.88%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.44%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.02%	97.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.56%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	87.99%	95.93%
CHEMBL4072	P07858	Cathepsin B	87.98%	93.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.45%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.26%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.04%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.01%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.03%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.43%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.77%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.29%	93.03%
CHEMBL5028	O14672	ADAM10	81.34%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.59%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.51%	99.23%
CHEMBL1871	P10275	Androgen Receptor	80.27%	96.43%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.25%	95.83%

Plants that contains it

• Tetragonotheca repanda

Cross-Links

• PubChem: 162935425
• LOTUS: LTS0002132
• wikiData: Q104954156