methyl (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3-ethyl-4-methylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylate

Details

• Internal ID: 17465b81-ac99-4ae5-9933-dd7ce5a013ed
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3-ethyl-4-methylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylate
• SMILES (Canonical): CCC(=CC(=O)OC1C2C34COC2(C(C(C3C5(C=C(C(=O)C(C5CC4OC1=O)C)OC6C(C(C(OC6O)CO)O)O)C)O)O)C(=O)OC)C(C)(C)OC(=O)C
• SMILES (Isomeric): CC/C(=C\C(=O)O[C@@H]1[C@@H]2[C@@]34CO[C@@]2([C@H]([C@@H]([C@@H]3[C@]5(C=C(C(=O)[C@H]([C@@H]5C[C@H]4OC1=O)C)O[C@@H]6[C@H]([C@@H]([C@H](O[C@H]6O)CO)O)O)C)O)O)C(=O)OC)/C(C)(C)OC(=O)C
• InChI: InChI=1S/C37H50O18/c1-8-16(34(4,5)55-15(3)39)9-21(40)54-27-29-36-13-50-37(29,33(48)49-7)30(45)25(44)28(36)35(6)11-18(22(41)14(2)17(35)10-20(36)53-32(27)47)51-26-24(43)23(42)19(12-38)52-31(26)46/h9,11,14,17,19-20,23-31,38,42-46H,8,10,12-13H2,1-7H3/b16-9+/t14-,17-,19+,20+,23+,24-,25+,26+,27+,28+,29+,30-,31+,35-,36+,37-/m0/s1
• InChI Key: KUWUPYZTOZNFMS-UIDIJMJPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₀O₁₈
• Molecular Weight: 782.80 g/mol
• Exact Mass: 782.29971474 g/mol
• Topological Polar Surface Area (TPSA): 271.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -1.66
• H-Bond Acceptor: 18
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8131	81.31%
Caco-2	-	0.8729	87.29%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7250	72.50%
OATP2B1 inhibitior	-	0.8651	86.51%
OATP1B1 inhibitior	+	0.8008	80.08%
OATP1B3 inhibitior	+	0.9383	93.83%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7591	75.91%
P-glycoprotein inhibitior	+	0.7604	76.04%
P-glycoprotein substrate	+	0.8138	81.38%
CYP3A4 substrate	+	0.7308	73.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8221	82.21%
CYP2C9 inhibition	-	0.8025	80.25%
CYP2C19 inhibition	-	0.8115	81.15%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	-	0.8774	87.74%
CYP2C8 inhibition	+	0.7232	72.32%
CYP inhibitory promiscuity	-	0.8222	82.22%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5908	59.08%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9090	90.90%
Skin irritation	-	0.7028	70.28%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3842	38.42%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5431	54.31%
skin sensitisation	-	0.8514	85.14%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.5566	55.66%
Acute Oral Toxicity (c)	III	0.6641	66.41%
Estrogen receptor binding	+	0.7970	79.70%
Androgen receptor binding	+	0.7454	74.54%
Thyroid receptor binding	+	0.5157	51.57%
Glucocorticoid receptor binding	+	0.7788	77.88%
Aromatase binding	+	0.6406	64.06%
PPAR gamma	+	0.7585	75.85%
Honey bee toxicity	-	0.6233	62.33%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9357	93.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.46%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	97.47%	97.79%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	97.08%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.85%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.78%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.08%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.91%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.68%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.34%	91.24%
CHEMBL221	P23219	Cyclooxygenase-1	90.53%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	90.50%	91.49%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.33%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.65%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.59%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	89.15%	92.88%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.14%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.27%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.91%	96.95%
CHEMBL5028	O14672	ADAM10	85.82%	97.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.34%	89.50%
CHEMBL230	P35354	Cyclooxygenase-2	84.40%	89.63%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.97%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.42%	94.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.95%	97.14%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.77%	98.75%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.31%	96.90%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.99%	95.56%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.83%	97.33%
CHEMBL3776	Q14790	Caspase-8	80.71%	97.06%

Plants that contains it

• Brucea javanica

Cross-Links

• PubChem: 162904166
• LOTUS: LTS0229159
• wikiData: Q105146387