(2R)-2-[3-[(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]pyridin-1-ium-1-yl]-3-phenylpropanoate

Details

• Internal ID: 3731b909-0c2a-4e1c-93e4-134f8fae6242
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2R)-2-[3-[(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]pyridin-1-ium-1-yl]-3-phenylpropanoate
• SMILES (Canonical): C=CC1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)C=CC3=C[N+](=CC=C3)C(CC4=CC=CC=C4)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=C[N+](=CC=C3)[C@H](CC4=CC=CC=C4)C(=O)[O-]
• InChI: InChI=1S/C30H33NO11/c1-2-19-20(11-10-18-9-6-12-31(14-18)22(28(38)39)13-17-7-4-3-5-8-17)21(27(36)37)16-40-29(19)42-30-26(35)25(34)24(33)23(15-32)41-30/h2-12,14,16,19-20,22-26,29-30,32-35H,1,13,15H2,(H-,36,37,38,39)/b11-10+/t19-,20+,22-,23-,24-,25+,26-,29+,30+/m1/s1
• InChI Key: NESGKYFUGBYZKP-PPHHKDQVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₃NO₁₁
• Molecular Weight: 583.60 g/mol
• Exact Mass: 583.20536087 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): -0.92
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9223	92.23%
Caco-2	-	0.8955	89.55%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Nucleus	0.4982	49.82%
OATP2B1 inhibitior	-	0.5642	56.42%
OATP1B1 inhibitior	+	0.7769	77.69%
OATP1B3 inhibitior	+	0.9379	93.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8675	86.75%
P-glycoprotein inhibitior	-	0.4606	46.06%
P-glycoprotein substrate	-	0.5481	54.81%
CYP3A4 substrate	+	0.6684	66.84%
CYP2C9 substrate	-	0.5975	59.75%
CYP2D6 substrate	-	0.8668	86.68%
CYP3A4 inhibition	-	0.9561	95.61%
CYP2C9 inhibition	-	0.7758	77.58%
CYP2C19 inhibition	-	0.8115	81.15%
CYP2D6 inhibition	-	0.8707	87.07%
CYP1A2 inhibition	-	0.7661	76.61%
CYP2C8 inhibition	+	0.7278	72.78%
CYP inhibitory promiscuity	-	0.8987	89.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5779	57.79%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9248	92.48%
Skin irritation	-	0.7831	78.31%
Skin corrosion	-	0.9361	93.61%
Ames mutagenesis	+	0.5477	54.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.4154	41.54%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8564	85.64%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7125	71.25%
Acute Oral Toxicity (c)	III	0.5729	57.29%
Estrogen receptor binding	+	0.7082	70.82%
Androgen receptor binding	+	0.7242	72.42%
Thyroid receptor binding	+	0.6032	60.32%
Glucocorticoid receptor binding	+	0.6531	65.31%
Aromatase binding	+	0.5700	57.00%
PPAR gamma	+	0.7436	74.36%
Honey bee toxicity	-	0.6127	61.27%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7158	71.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.17%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.57%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.49%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.09%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	87.59%	87.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.37%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.24%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.87%	99.17%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	85.18%	88.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.46%	94.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.73%	94.08%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.51%	83.57%
CHEMBL1255126	O15151	Protein Mdm4	83.30%	90.20%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.97%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.64%	91.71%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.99%	96.09%

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: 76309955
• NPASS: NPC50997
• ChEMBL: CHEMBL3092665