methyl (1R,2S,3R,6R,8S,9S,10S,11R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4-oxo-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate

Details

• Internal ID: 60fea489-a6f6-47b0-9edd-481f408ce0c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,10S,11R,13S,14R,15R,16S,17S)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4-oxo-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate
• SMILES (Canonical): CC1C2CC3C45COC(C4C(C(=O)O3)OC(=O)C=C(C)C)(C(C(C5C2(CC(C1O)OC6C(C(C(C(O6)CO)O)O)O)C)O)O)C(=O)OC
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@@H]3[C@@]45CO[C@@]([C@@H]4[C@H](C(=O)O3)OC(=O)C=C(C)C)([C@H]([C@@H]([C@@H]5[C@]2(C[C@H]([C@H]1O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)O)C(=O)OC
• InChI: InChI=1S/C32H46O16/c1-11(2)6-17(34)48-23-25-31-10-44-32(25,29(42)43-5)26(40)22(39)24(31)30(4)8-14(18(35)12(3)13(30)7-16(31)47-27(23)41)45-28-21(38)20(37)19(36)15(9-33)46-28/h6,12-16,18-26,28,33,35-40H,7-10H2,1-5H3/t12-,13-,14+,15+,16+,18-,19+,20-,21+,22+,23+,24+,25+,26-,28+,30-,31+,32-/m0/s1
• InChI Key: POUGEQYQLBGWLB-OASHSOORSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₆O₁₆
• Molecular Weight: 686.70 g/mol
• Exact Mass: 686.27858538 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -2.70
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7682	76.82%
Caco-2	-	0.8790	87.90%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7661	76.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8282	82.82%
OATP1B3 inhibitior	+	0.9135	91.35%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7689	76.89%
P-glycoprotein inhibitior	+	0.6505	65.05%
P-glycoprotein substrate	+	0.7861	78.61%
CYP3A4 substrate	+	0.7228	72.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8920	89.20%
CYP3A4 inhibition	-	0.8843	88.43%
CYP2C9 inhibition	-	0.8215	82.15%
CYP2C19 inhibition	-	0.8570	85.70%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.8924	89.24%
CYP2C8 inhibition	+	0.5897	58.97%
CYP inhibitory promiscuity	-	0.9127	91.27%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6114	61.14%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9207	92.07%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6849	68.49%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5392	53.92%
skin sensitisation	-	0.8716	87.16%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5510	55.10%
Acute Oral Toxicity (c)	I	0.4259	42.59%
Estrogen receptor binding	+	0.7695	76.95%
Androgen receptor binding	+	0.6931	69.31%
Thyroid receptor binding	-	0.5893	58.93%
Glucocorticoid receptor binding	+	0.6150	61.50%
Aromatase binding	+	0.6773	67.73%
PPAR gamma	+	0.7257	72.57%
Honey bee toxicity	-	0.5697	56.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9727	97.27%

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	98.69%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.38%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.99%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.99%	96.00%
CHEMBL2996	Q05655	Protein kinase C delta	90.09%	97.79%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.64%	91.24%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.18%	96.21%
CHEMBL2581	P07339	Cathepsin D	88.60%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.56%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.07%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.07%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.12%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.72%	86.33%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.16%	97.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.13%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.00%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.87%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.96%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.87%	89.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.28%	95.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.56%	97.28%
CHEMBL5028	O14672	ADAM10	82.57%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.04%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.90%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.60%	95.83%
CHEMBL5255	O00206	Toll-like receptor 4	81.31%	92.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.90%	96.47%
CHEMBL1951	P21397	Monoamine oxidase A	80.89%	91.49%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.43%	89.50%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 11250992
• NPASS: NPC305315
• LOTUS: LTS0148300
• wikiData: Q105216850