(2S)-2-[3-[(E)-2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]pyridin-1-ium-1-yl]propanoate

Details

• Internal ID: 73daf8e9-2927-4481-a90c-45b31955f856
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S)-2-[3-[(E)-2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]pyridin-1-ium-1-yl]propanoate
• SMILES (Canonical): CC(C(=O)[O-])[N+]1=CC=CC(=C1)C=CC2C(C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)C=C
• SMILES (Isomeric): C[C@@H](C(=O)[O-])[N+]1=CC=CC(=C1)/C=C/[C@H]2[C@H]([C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C=C
• InChI: InChI=1S/C25H31NO11/c1-4-15-16(8-7-14-6-5-9-26(10-14)13(2)22(31)32)17(23(33)34-3)12-35-24(15)37-25-21(30)20(29)19(28)18(11-27)36-25/h4-10,12-13,15-16,18-21,24-25,27-30H,1,11H2,2-3H3/b8-7+/t13-,15+,16-,18+,19+,20-,21+,24-,25-/m0/s1
• InChI Key: FWQZWKQALMIFIJ-ULVSZBDPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₁NO₁₁
• Molecular Weight: 521.50 g/mol
• Exact Mass: 521.18971080 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -2.05
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9664	96.64%
Caco-2	-	0.8709	87.09%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.4765	47.65%
OATP2B1 inhibitior	-	0.7109	71.09%
OATP1B1 inhibitior	+	0.7884	78.84%
OATP1B3 inhibitior	+	0.9412	94.12%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7207	72.07%
P-glycoprotein inhibitior	-	0.5434	54.34%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6741	67.41%
CYP2C9 substrate	-	0.8010	80.10%
CYP2D6 substrate	-	0.8747	87.47%
CYP3A4 inhibition	-	0.9443	94.43%
CYP2C9 inhibition	-	0.8145	81.45%
CYP2C19 inhibition	-	0.7745	77.45%
CYP2D6 inhibition	-	0.8596	85.96%
CYP1A2 inhibition	-	0.7789	77.89%
CYP2C8 inhibition	+	0.6548	65.48%
CYP inhibitory promiscuity	-	0.8995	89.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5540	55.40%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9401	94.01%
Skin irritation	-	0.7888	78.88%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6442	64.42%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.7048	70.48%
skin sensitisation	-	0.8576	85.76%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.5877	58.77%
Acute Oral Toxicity (c)	III	0.6127	61.27%
Estrogen receptor binding	+	0.6316	63.16%
Androgen receptor binding	+	0.6284	62.84%
Thyroid receptor binding	+	0.6331	63.31%
Glucocorticoid receptor binding	+	0.5792	57.92%
Aromatase binding	+	0.5461	54.61%
PPAR gamma	+	0.6011	60.11%
Honey bee toxicity	-	0.7265	72.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.4856	48.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.34%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.19%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.28%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	94.74%	94.73%
CHEMBL2581	P07339	Cathepsin D	91.30%	98.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.08%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.96%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.64%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.19%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.58%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.45%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.34%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.37%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.53%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.59%	100.00%

Plants that contains it

• Acacia aulacocarpa
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Cryptocarya aschersoniana
• Eupatorium argentinum
• Garcinia madruno
• Guatteria ucayalina
• Juniperus brevifolia
• Lonicera japonica
• Peritassa compta
• Psiadia dentata

Cross-Links

• PubChem: 76335389
• NPASS: NPC127647