methyl (1R,2S,3R,6R,8S,9S,13S,14S,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-[(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-10-ene-17-carboxylate

Details

• Internal ID: f974d65d-99ba-4ff9-9cbc-f47204f0a593
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,13S,14S,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,12-dioxo-11-[(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-10-ene-17-carboxylate
• SMILES (Canonical): CC1C=C(C(=O)C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(OC5)C(=O)OC)O)O)C)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C=C(C(=O)[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=C(\C)/C(C)C)(OC5)C(=O)OC)O)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C34H46O16/c1-12(2)13(3)8-19(36)50-24-26-33-11-46-34(26,31(44)45-6)28(42)23(40)25(33)32(5)15(9-18(33)49-29(24)43)14(4)7-16(27(32)41)47-30-22(39)21(38)20(37)17(10-35)48-30/h7-8,12,14-15,17-18,20-26,28,30,35,37-40,42H,9-11H2,1-6H3/b13-8+/t14-,15+,17-,18-,20-,21+,22-,23-,24-,25-,26-,28+,30-,32+,33-,34+/m1/s1
• InChI Key: YSFALLIAQRJCQF-JTCMMNOTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₆O₁₆
• Molecular Weight: 710.70 g/mol
• Exact Mass: 710.27858538 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -1.73
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7012	70.12%
Caco-2	-	0.8689	86.89%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.8212	82.12%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8105	81.05%
P-glycoprotein inhibitior	+	0.7232	72.32%
P-glycoprotein substrate	+	0.7897	78.97%
CYP3A4 substrate	+	0.7153	71.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.8951	89.51%
CYP2C9 inhibition	-	0.8400	84.00%
CYP2C19 inhibition	-	0.8450	84.50%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	-	0.8917	89.17%
CYP2C8 inhibition	+	0.6301	63.01%
CYP inhibitory promiscuity	-	0.8718	87.18%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5995	59.95%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9150	91.50%
Skin irritation	-	0.7143	71.43%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6774	67.74%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5374	53.74%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6221	62.21%
Acute Oral Toxicity (c)	III	0.5883	58.83%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.7060	70.60%
Thyroid receptor binding	-	0.5214	52.14%
Glucocorticoid receptor binding	+	0.7299	72.99%
Aromatase binding	+	0.6637	66.37%
PPAR gamma	+	0.7489	74.89%
Honey bee toxicity	-	0.5584	55.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9128	91.28%

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	99.72%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.67%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.74%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.38%	96.00%
CHEMBL4072	P07858	Cathepsin B	96.86%	93.67%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	96.21%	89.34%
CHEMBL2581	P07339	Cathepsin D	96.00%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.89%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.90%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.23%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.49%	95.56%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.41%	98.75%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	88.17%	95.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.96%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.87%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.64%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.04%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.98%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.77%	91.24%
CHEMBL3837	P07711	Cathepsin L	86.10%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.62%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	84.17%	97.79%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.12%	89.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.09%	94.33%
CHEMBL3401	O75469	Pregnane X receptor	83.92%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.80%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.96%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	82.90%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.18%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	80.51%	83.82%
CHEMBL5028	O14672	ADAM10	80.36%	97.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.02%	95.83%

Plants that contains it

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

Cross-Links

• PubChem: 101659164
• NPASS: NPC241365
• LOTUS: LTS0262730
• wikiData: Q105341328