methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-benzoyloxy-15,16-dihydroxy-9,13-dimethyl-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: 1f7abf8c-6b17-493f-8281-8e8504868261
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-benzoyloxy-15,16-dihydroxy-9,13-dimethyl-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(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C6=CC=CC=C6)(OC5)C(=O)OC)O)O)C)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): CC1=C(C(=O)C[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)C6=CC=CC=C6)(OC5)C(=O)OC)O)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C34H40O16/c1-13-15-9-18-33-12-46-34(31(44)45-3,26(33)24(29(43)48-18)49-28(42)14-7-5-4-6-8-14)27(41)22(40)25(33)32(15,2)10-16(36)23(13)50-30-21(39)20(38)19(37)17(11-35)47-30/h4-8,15,17-22,24-27,30,35,37-41H,9-12H2,1-3H3/t15-,17+,18+,19+,20-,21+,22+,24+,25+,26+,27-,30-,32-,33+,34-/m0/s1
• InChI Key: CETPXHIOCLMKFO-BPIPPOPGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₀O₁₆
• Molecular Weight: 704.70 g/mol
• Exact Mass: 704.23163518 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.88
• 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	+	0.7709	77.09%
Caco-2	-	0.8751	87.51%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6842	68.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8350	83.50%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7712	77.12%
P-glycoprotein inhibitior	+	0.7252	72.52%
P-glycoprotein substrate	+	0.7347	73.47%
CYP3A4 substrate	+	0.7110	71.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8841	88.41%
CYP3A4 inhibition	-	0.8327	83.27%
CYP2C9 inhibition	-	0.8701	87.01%
CYP2C19 inhibition	-	0.8508	85.08%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	-	0.8666	86.66%
CYP2C8 inhibition	+	0.6899	68.99%
CYP inhibitory promiscuity	-	0.8855	88.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6156	61.56%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9199	91.99%
Skin irritation	-	0.6950	69.50%
Skin corrosion	-	0.9442	94.42%
Ames mutagenesis	-	0.5477	54.77%
Human Ether-a-go-go-Related Gene inhibition	+	0.7497	74.97%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5966	59.66%
skin sensitisation	-	0.8802	88.02%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6180	61.80%
Acute Oral Toxicity (c)	I	0.5567	55.67%
Estrogen receptor binding	+	0.7946	79.46%
Androgen receptor binding	+	0.7089	70.89%
Thyroid receptor binding	-	0.4876	48.76%
Glucocorticoid receptor binding	+	0.7099	70.99%
Aromatase binding	+	0.5800	58.00%
PPAR gamma	+	0.7251	72.51%
Honey bee toxicity	-	0.6615	66.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9841	98.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.70%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.42%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.19%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.11%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.01%	96.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.84%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.73%	95.56%
CHEMBL5028	O14672	ADAM10	90.65%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	89.09%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.78%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.68%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	86.44%	97.79%
CHEMBL220	P22303	Acetylcholinesterase	85.43%	94.45%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	84.97%	87.67%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.89%	96.47%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.90%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.82%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.56%	93.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.59%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.00%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.24%	96.21%

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: 11411443
• NPASS: NPC163908
• LOTUS: LTS0172865
• wikiData: Q104956040