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

Details

• Internal ID: a452fa14-b960-4e28-a896-68793762c181
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S)-4-[(E)-2-[5-carboxy-1-[(1S,2S)-1-carboxy-2-methylbutyl]pyridin-1-ium-3-yl]ethenyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
• SMILES (Canonical): CCC(C)C(C(=O)O)[N+]1=CC(=CC(=C1)C(=O)O)C=CC2C(C(OC=C2C(=O)[O-])OC3C(C(C(C(O3)CO)O)O)O)C=C
• SMILES (Isomeric): CC[C@H](C)[C@@H](C(=O)O)[N+]1=CC(=CC(=C1)C(=O)O)/C=C/[C@H]2[C@H]([C@@H](OC=C2C(=O)[O-])O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C=C
• InChI: InChI=1S/C28H35NO13/c1-4-13(3)20(26(38)39)29-9-14(8-15(10-29)24(34)35)6-7-17-16(5-2)27(40-12-18(17)25(36)37)42-28-23(33)22(32)21(31)19(11-30)41-28/h5-10,12-13,16-17,19-23,27-28,30-33H,2,4,11H2,1,3H3,(H2-,34,35,36,37,38,39)/b7-6+/t13-,16+,17-,19+,20-,21+,22-,23+,27-,28-/m0/s1
• InChI Key: PBSWZDXYMMYYEU-VYNQEGOFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₅NO₁₃
• Molecular Weight: 593.60 g/mol
• Exact Mass: 593.21084017 g/mol
• Topological Polar Surface Area (TPSA): 227.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): -1.42
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9396	93.96%
Caco-2	-	0.9012	90.12%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.3582	35.82%
OATP2B1 inhibitior	-	0.7202	72.02%
OATP1B1 inhibitior	+	0.7626	76.26%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6485	64.85%
P-glycoprotein inhibitior	-	0.4819	48.19%
P-glycoprotein substrate	-	0.5565	55.65%
CYP3A4 substrate	+	0.6388	63.88%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8726	87.26%
CYP3A4 inhibition	-	0.9216	92.16%
CYP2C9 inhibition	-	0.7793	77.93%
CYP2C19 inhibition	-	0.7097	70.97%
CYP2D6 inhibition	-	0.8743	87.43%
CYP1A2 inhibition	-	0.7215	72.15%
CYP2C8 inhibition	+	0.6462	64.62%
CYP inhibitory promiscuity	-	0.8475	84.75%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5042	50.42%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9284	92.84%
Skin irritation	-	0.7839	78.39%
Skin corrosion	-	0.9361	93.61%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7256	72.56%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5920	59.20%
Acute Oral Toxicity (c)	III	0.6268	62.68%
Estrogen receptor binding	+	0.7367	73.67%
Androgen receptor binding	+	0.6153	61.53%
Thyroid receptor binding	+	0.5470	54.70%
Glucocorticoid receptor binding	+	0.5841	58.41%
Aromatase binding	+	0.5717	57.17%
PPAR gamma	+	0.6129	61.29%
Honey bee toxicity	-	0.7314	73.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.8303	83.03%

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+]	97.45%	83.57%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.47%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.64%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.85%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.55%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.54%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.25%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.83%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.60%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.37%	96.95%
CHEMBL1811	P34995	Prostanoid EP1 receptor	86.99%	95.71%
CHEMBL226	P30542	Adenosine A1 receptor	86.87%	95.93%
CHEMBL2581	P07339	Cathepsin D	86.80%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	86.39%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.54%	97.21%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.91%	93.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.84%	96.21%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.72%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.15%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.15%	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: 76317186
• NPASS: NPC25442