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

Details

• Internal ID: 416d75e7-e20f-44a2-a0e8-11a97806935c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: 5-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(2-hydroxyethyl)pyridin-1-ium-3-carboxylate
• SMILES (Canonical): C=CC1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)C=CC3=CC(=C[N+](=C3)CCO)C(=O)[O-]
• SMILES (Isomeric): C=C[C@@H]1[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)/C=C/C3=CC(=C[N+](=C3)CCO)C(=O)[O-]
• InChI: InChI=1S/C24H29NO12/c1-2-14-15(4-3-12-7-13(21(31)32)9-25(8-12)5-6-26)16(22(33)34)11-35-23(14)37-24-20(30)19(29)18(28)17(10-27)36-24/h2-4,7-9,11,14-15,17-20,23-24,26-30H,1,5-6,10H2,(H-,31,32,33,34)/b4-3+/t14-,15+,17-,18-,19+,20-,23+,24+/m1/s1
• InChI Key: DXFHNEGQVDLRDO-KBCYOOEFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₉NO₁₂
• Molecular Weight: 523.50 g/mol
• Exact Mass: 523.16897536 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -3.10
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9423	94.23%
Caco-2	-	0.9114	91.14%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4172	41.72%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.7600	76.00%
OATP1B3 inhibitior	+	0.9381	93.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5616	56.16%
P-glycoprotein inhibitior	-	0.5742	57.42%
P-glycoprotein substrate	-	0.6641	66.41%
CYP3A4 substrate	+	0.6301	63.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8712	87.12%
CYP3A4 inhibition	-	0.9085	90.85%
CYP2C9 inhibition	-	0.7320	73.20%
CYP2C19 inhibition	-	0.8172	81.72%
CYP2D6 inhibition	-	0.8894	88.94%
CYP1A2 inhibition	-	0.7431	74.31%
CYP2C8 inhibition	+	0.6760	67.60%
CYP inhibitory promiscuity	-	0.9277	92.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5662	56.62%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9333	93.33%
Skin irritation	-	0.7647	76.47%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	+	0.5807	58.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.5232	52.32%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.6680	66.80%
skin sensitisation	-	0.8518	85.18%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6440	64.40%
Acute Oral Toxicity (c)	III	0.5630	56.30%
Estrogen receptor binding	+	0.6752	67.52%
Androgen receptor binding	+	0.5652	56.52%
Thyroid receptor binding	+	0.5293	52.93%
Glucocorticoid receptor binding	+	0.5744	57.44%
Aromatase binding	+	0.6457	64.57%
PPAR gamma	+	0.6700	67.00%
Honey bee toxicity	-	0.7074	70.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.7095	70.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	98.47%	83.57%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.50%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.40%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.73%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.67%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.52%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.51%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.84%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	89.40%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.35%	95.56%
CHEMBL1811	P34995	Prostanoid EP1 receptor	87.99%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.25%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.16%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	84.40%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.06%	96.95%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	82.46%	88.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.86%	95.93%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.03%	89.34%
CHEMBL5255	O00206	Toll-like receptor 4	80.94%	92.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.42%	89.44%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.09%	90.71%

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: 24879106
• NPASS: NPC59033