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

Details

• Internal ID: 4a7a51a7-7b85-4785-9a4f-c397fe40faba
• 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)-12,15,16-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]nonadec-9-ene-17-carboxylate
• SMILES (Canonical): CC1=CC(C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)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=C(C)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/C32H44O16/c1-11(2)6-17(34)48-22-24-31-10-44-32(24,29(42)43-5)26(40)21(38)23(31)30(4)13(8-16(31)47-27(22)41)12(3)7-14(25(30)39)45-28-20(37)19(36)18(35)15(9-33)46-28/h6-7,13-16,18-26,28,33,35-40H,8-10H2,1-5H3/t13-,14-,15+,16+,18+,19-,20+,21+,22+,23+,24+,25+,26-,28+,30-,31+,32-/m0/s1
• InChI Key: IZUDZNKPPXKFJY-DXMXMRDXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₄O₁₆
• Molecular Weight: 684.70 g/mol
• Exact Mass: 684.26293531 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.78
• 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	+	0.7012	70.12%
Caco-2	-	0.8739	87.39%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8378	83.78%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8665	86.65%
P-glycoprotein inhibitior	+	0.6652	66.52%
P-glycoprotein substrate	+	0.8169	81.69%
CYP3A4 substrate	+	0.7151	71.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8920	89.20%
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	+	0.5440	54.40%
CYP inhibitory promiscuity	-	0.8718	87.18%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5995	59.95%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9163	91.63%
Skin irritation	-	0.7143	71.43%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6889	68.89%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5392	53.92%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6078	60.78%
Acute Oral Toxicity (c)	III	0.5883	58.83%
Estrogen receptor binding	+	0.7942	79.42%
Androgen receptor binding	+	0.6954	69.54%
Thyroid receptor binding	-	0.5524	55.24%
Glucocorticoid receptor binding	+	0.6733	67.33%
Aromatase binding	+	0.6672	66.72%
PPAR gamma	+	0.7428	74.28%
Honey bee toxicity	-	0.5584	55.84%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	98.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.49%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.41%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.21%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	90.84%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.99%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.49%	94.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.96%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.80%	91.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.20%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.20%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.09%	97.28%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.30%	97.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.13%	97.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.12%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.94%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.81%	91.07%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.63%	89.34%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.38%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.37%	96.47%
CHEMBL5255	O00206	Toll-like receptor 4	84.32%	92.50%
CHEMBL5028	O14672	ADAM10	83.50%	97.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.50%	98.75%
CHEMBL4208	P20618	Proteasome component C5	82.97%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.55%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.07%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.77%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.33%	99.17%

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: 101659160
• NPASS: NPC45659
• LOTUS: LTS0253449
• wikiData: Q104399321