Methyl (1R,2R,6S,7R,8R,13R,14R,15R,16S,17S)-15,16-dihydroxy-9,13-dimethyl-7-(3-methylbut-2-enoyloxy)-4,11-dioxo-10-[(2S,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]nonadec-9-ene-17-carboxylate

Details

• Internal ID: 552e4532-d99a-4111-b27f-53f65dc59e86
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2R,6S,7R,8R,13R,14R,15R,16S,17S)-15,16-dihydroxy-9,13-dimethyl-7-(3-methylbut-2-enoyloxy)-4,11-dioxo-10-[(2S,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]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CC1=C(C(=O)CC2(C1C(C3C45C2C(C(C(C4CC(=O)O3)(OC5)C(=O)OC)O)O)OC(=O)C=C(C)C)C)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): CC1=C(C(=O)C[C@]2([C@H]1[C@H]([C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4CC(=O)O3)(OC5)C(=O)OC)O)O)OC(=O)C=C(C)C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C32H42O16/c1-11(2)6-16(35)46-24-18-12(3)23(48-28-21(39)20(38)19(37)14(9-33)45-28)13(34)8-30(18,4)25-22(40)26(41)32(29(42)43-5)15-7-17(36)47-27(24)31(15,25)10-44-32/h6,14-15,18-22,24-28,33,37-41H,7-10H2,1-5H3/t14-,15-,18-,19-,20+,21-,22-,24-,25-,26+,27-,28+,30+,31+,32+/m1/s1
• InChI Key: ASOOSZCOBHWYHJ-DGGNSZFLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₆
• Molecular Weight: 682.70 g/mol
• Exact Mass: 682.24728525 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -2.22
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6627	66.27%
Caco-2	-	0.8733	87.33%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7740	77.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8271	82.71%
OATP1B3 inhibitior	+	0.9226	92.26%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9265	92.65%
P-glycoprotein inhibitior	+	0.7112	71.12%
P-glycoprotein substrate	+	0.6350	63.50%
CYP3A4 substrate	+	0.7206	72.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.8559	85.59%
CYP2C9 inhibition	-	0.8085	80.85%
CYP2C19 inhibition	-	0.8335	83.35%
CYP2D6 inhibition	-	0.9381	93.81%
CYP1A2 inhibition	-	0.9005	90.05%
CYP2C8 inhibition	+	0.6340	63.40%
CYP inhibitory promiscuity	-	0.8853	88.53%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5635	56.35%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9163	91.63%
Skin irritation	-	0.7196	71.96%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.6277	62.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.4144	41.44%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6479	64.79%
skin sensitisation	-	0.8596	85.96%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7417	74.17%
Acute Oral Toxicity (c)	III	0.4750	47.50%
Estrogen receptor binding	+	0.7841	78.41%
Androgen receptor binding	+	0.7149	71.49%
Thyroid receptor binding	-	0.5391	53.91%
Glucocorticoid receptor binding	+	0.6801	68.01%
Aromatase binding	+	0.6658	66.58%
PPAR gamma	+	0.7306	73.06%
Honey bee toxicity	-	0.6064	60.64%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9505	95.05%

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	97.98%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.39%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	95.82%	98.03%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.58%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.45%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	94.82%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.26%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.73%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.18%	91.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.86%	96.00%
CHEMBL5028	O14672	ADAM10	89.76%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.66%	89.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	88.20%	97.47%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.12%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.73%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.23%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.07%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.71%	94.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.03%	93.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.35%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.25%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.05%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.58%	95.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.50%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.28%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.23%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	80.95%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.77%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.47%	95.83%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.24%	94.80%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.17%	96.90%

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: 21115217
• NPASS: NPC193087