methyl (1R,2S,3R,6R,8S,11S,12S,13S,14R,15R,16S,17S)-3-acetyloxy-12,15,16-trihydroxy-9,13-dimethyl-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]nonadec-9-ene-17-carboxylate

Details

• Internal ID: ba36e9a9-ccfa-4b47-9df9-02acb66fa9c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,11S,12S,13S,14R,15R,16S,17S)-3-acetyloxy-12,15,16-trihydroxy-9,13-dimethyl-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]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CC1=CC(C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C)(OC5)C(=O)OC)O)O)C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): CC1=C[C@@H]([C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)C)(OC5)C(=O)OC)O)O)C)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C29H40O16/c1-9-5-12(43-25-17(34)16(33)15(32)13(7-30)44-25)22(36)27(3)11(9)6-14-28-8-41-29(26(39)40-4,23(37)18(35)20(27)28)21(28)19(24(38)45-14)42-10(2)31/h5,11-23,25,30,32-37H,6-8H2,1-4H3/t11-,12-,13+,14+,15+,16-,17+,18+,19+,20+,21+,22+,23-,25+,27-,28+,29-/m0/s1
• InChI Key: IPVONKABOQLBGH-POUVBQLVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₁₆
• Molecular Weight: 644.60 g/mol
• Exact Mass: 644.23163518 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.73
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6522	65.22%
Caco-2	-	0.8766	87.66%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6854	68.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8322	83.22%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4601	46.01%
P-glycoprotein inhibitior	+	0.6114	61.14%
P-glycoprotein substrate	+	0.7676	76.76%
CYP3A4 substrate	+	0.7133	71.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.9093	90.93%
CYP2C9 inhibition	-	0.8958	89.58%
CYP2C19 inhibition	-	0.8739	87.39%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.9020	90.20%
CYP2C8 inhibition	+	0.4623	46.23%
CYP inhibitory promiscuity	-	0.8845	88.45%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6083	60.83%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.6919	69.19%
Skin corrosion	-	0.9356	93.56%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4109	41.09%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8691	86.91%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6934	69.34%
Acute Oral Toxicity (c)	III	0.5125	51.25%
Estrogen receptor binding	+	0.7694	76.94%
Androgen receptor binding	+	0.6830	68.30%
Thyroid receptor binding	-	0.5941	59.41%
Glucocorticoid receptor binding	+	0.6528	65.28%
Aromatase binding	+	0.6486	64.86%
PPAR gamma	+	0.6903	69.03%
Honey bee toxicity	-	0.6064	60.64%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8813	88.13%

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	98.97%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.36%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.75%	96.00%
CHEMBL2581	P07339	Cathepsin D	93.55%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.28%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.29%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.07%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.97%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.13%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.00%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.14%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.07%	86.33%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.86%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.63%	94.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.53%	97.28%
CHEMBL2996	Q05655	Protein kinase C delta	84.52%	97.79%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.15%	97.47%
CHEMBL5255	O00206	Toll-like receptor 4	83.95%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.43%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.21%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.12%	96.77%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.72%	81.11%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.63%	95.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.61%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.11%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.87%	96.47%
CHEMBL5028	O14672	ADAM10	81.57%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.16%	99.17%
CHEMBL4208	P20618	Proteasome component C5	81.07%	90.00%

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: 101659159
• NPASS: NPC281693
• LOTUS: LTS0189031
• wikiData: Q105117527