[(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl pyridine-2-carboxylate

Details

• Internal ID: f3fb28c6-fbd4-4468-9eca-37b7aba998de
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(3S,4R,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl pyridine-2-carboxylate
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=CC=C(C=C3)CCO)CO)O)O)O)(COC(=O)C4=CC=CC=N4)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC=C(C=C3)CCO)CO)O)O)O)(COC(=O)C4=CC=CC=N4)O
• InChI: InChI=1S/C25H31NO12/c27-10-8-14-4-6-15(7-5-14)36-23-20(19(30)18(29)17(11-28)37-23)38-24-21(31)25(33,13-35-24)12-34-22(32)16-3-1-2-9-26-16/h1-7,9,17-21,23-24,27-31,33H,8,10-13H2/t17-,18-,19+,20-,21+,23-,24+,25-/m1/s1
• InChI Key: CRSDKJHRLZLQLO-KXQNOTADSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₁NO₁₂
• Molecular Weight: 537.50 g/mol
• Exact Mass: 537.18462542 g/mol
• Topological Polar Surface Area (TPSA): 198.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.88
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6333	63.33%
Caco-2	-	0.8805	88.05%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5630	56.30%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.8937	89.37%
OATP1B3 inhibitior	+	0.9445	94.45%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9213	92.13%
P-glycoprotein inhibitior	-	0.4813	48.13%
P-glycoprotein substrate	-	0.5797	57.97%
CYP3A4 substrate	+	0.6860	68.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.9144	91.44%
CYP2C9 inhibition	-	0.8454	84.54%
CYP2C19 inhibition	-	0.8783	87.83%
CYP2D6 inhibition	-	0.8850	88.50%
CYP1A2 inhibition	-	0.7794	77.94%
CYP2C8 inhibition	+	0.7526	75.26%
CYP inhibitory promiscuity	-	0.7145	71.45%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.8160	81.60%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7284	72.84%
Micronuclear	-	0.5226	52.26%
Hepatotoxicity	-	0.6265	62.65%
skin sensitisation	-	0.8423	84.23%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8577	85.77%
Acute Oral Toxicity (c)	III	0.6035	60.35%
Estrogen receptor binding	+	0.7864	78.64%
Androgen receptor binding	+	0.5980	59.80%
Thyroid receptor binding	+	0.5151	51.51%
Glucocorticoid receptor binding	+	0.6281	62.81%
Aromatase binding	+	0.6964	69.64%
PPAR gamma	+	0.6919	69.19%
Honey bee toxicity	-	0.6924	69.24%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.8479	84.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	98.99%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.97%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.29%	94.00%
CHEMBL230	P35354	Cyclooxygenase-2	96.00%	89.63%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.71%	94.62%
CHEMBL2243	O00519	Anandamide amidohydrolase	95.10%	97.53%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.12%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.72%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.73%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.72%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.62%	94.73%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	86.10%	92.67%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.02%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.97%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.80%	94.45%
CHEMBL4208	P20618	Proteasome component C5	83.31%	90.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.45%	91.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.10%	96.00%
CHEMBL2581	P07339	Cathepsin D	81.70%	98.95%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.40%	94.97%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.93%	92.62%
CHEMBL3902	P09211	Glutathione S-transferase Pi	80.87%	93.81%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.44%	94.23%
CHEMBL3891	P07384	Calpain 1	80.41%	93.04%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.33%	86.92%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.07%	94.00%

Plants that contains it

• Cucurbita pepo

Cross-Links

• PubChem: 163103727
• LOTUS: LTS0206583
• wikiData: Q104968794