methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-3-propanoyloxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate

Details

• Internal ID: 32ff16d0-8ba0-41b1-acfa-ac976fc77d76
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-3-propanoyloxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CCC(=O)OC1C2C34COC2(C(C(C3C5(CC(=O)C(=C(C5CC4OC1=O)C)O)C)O)O)C(=O)OC
• SMILES (Isomeric): CCC(=O)O[C@@H]1[C@@H]2[C@@]34CO[C@@]2([C@H]([C@@H]([C@@H]3[C@]5(CC(=O)C(=C([C@@H]5C[C@H]4OC1=O)C)O)C)O)O)C(=O)OC
• InChI: InChI=1S/C24H30O11/c1-5-13(26)35-16-18-23-8-33-24(18,21(31)32-4)19(29)15(28)17(23)22(3)7-11(25)14(27)9(2)10(22)6-12(23)34-20(16)30/h10,12,15-19,27-29H,5-8H2,1-4H3/t10-,12+,15+,16+,17+,18+,19-,22-,23+,24-/m0/s1
• InChI Key: JMNCUIIGFZOUJI-WUXZYLOCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₁
• Molecular Weight: 494.50 g/mol
• Exact Mass: 494.17881177 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.04
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9585	95.85%
Caco-2	-	0.7115	71.15%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7684	76.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8465	84.65%
OATP1B3 inhibitior	+	0.9303	93.03%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6727	67.27%
P-glycoprotein inhibitior	+	0.5827	58.27%
P-glycoprotein substrate	+	0.9028	90.28%
CYP3A4 substrate	+	0.7029	70.29%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.8848	88.48%
CYP3A4 inhibition	-	0.6909	69.09%
CYP2C9 inhibition	-	0.8174	81.74%
CYP2C19 inhibition	-	0.8313	83.13%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.8419	84.19%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8631	86.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5726	57.26%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9127	91.27%
Skin irritation	-	0.5753	57.53%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5620	56.20%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8837	88.37%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6548	65.48%
Acute Oral Toxicity (c)	III	0.5438	54.38%
Estrogen receptor binding	+	0.7763	77.63%
Androgen receptor binding	+	0.6739	67.39%
Thyroid receptor binding	-	0.5065	50.65%
Glucocorticoid receptor binding	+	0.7630	76.30%
Aromatase binding	+	0.6674	66.74%
PPAR gamma	+	0.6436	64.36%
Honey bee toxicity	-	0.6252	62.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9903	99.03%

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	99.91%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.84%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.89%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.37%	96.77%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.74%	96.95%
CHEMBL299	P17252	Protein kinase C alpha	92.44%	98.03%
CHEMBL2581	P07339	Cathepsin D	92.38%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.67%	96.38%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.46%	96.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.30%	96.21%
CHEMBL2996	Q05655	Protein kinase C delta	89.81%	97.79%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.65%	95.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.86%	94.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.83%	97.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.93%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.64%	97.28%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.34%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.05%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.62%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.61%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.51%	91.07%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.13%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.60%	97.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.27%	99.23%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.05%	89.50%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.97%	90.93%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.32%	96.47%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.24%	95.71%
CHEMBL5028	O14672	ADAM10	81.43%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.13%	99.17%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.25%	93.03%
CHEMBL5255	O00206	Toll-like receptor 4	80.20%	92.50%

Plants that contains it

• Brucea javanica

Cross-Links

• PubChem: 44361173
• NPASS: NPC323821
• ChEMBL: CHEMBL143600