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

Details

• Internal ID: 02ed15f9-5eaa-4233-b30c-785fd6ebd292
• 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-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]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)CO)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)CO)CO)O)O)O)(COC(=O)C4=CC=CC=N4)O
• InChI: InChI=1S/C24H29NO12/c26-9-13-4-6-14(7-5-13)35-22-19(18(29)17(28)16(10-27)36-22)37-23-20(30)24(32,12-34-23)11-33-21(31)15-3-1-2-8-25-15/h1-8,16-20,22-23,26-30,32H,9-12H2/t16-,17-,18+,19-,20+,22-,23+,24-/m1/s1
• InChI Key: XWINDNDXLPMAED-JALRXJJFSA-N
• Popularity: 0 references 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): 198.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.92
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6446	64.46%
Caco-2	-	0.8784	87.84%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.4588	45.88%
OATP2B1 inhibitior	-	0.8517	85.17%
OATP1B1 inhibitior	+	0.9058	90.58%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8257	82.57%
P-glycoprotein inhibitior	-	0.5434	54.34%
P-glycoprotein substrate	-	0.6665	66.65%
CYP3A4 substrate	+	0.6762	67.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.9250	92.50%
CYP2C9 inhibition	-	0.9100	91.00%
CYP2C19 inhibition	-	0.9140	91.40%
CYP2D6 inhibition	-	0.8772	87.72%
CYP1A2 inhibition	-	0.7948	79.48%
CYP2C8 inhibition	+	0.7054	70.54%
CYP inhibitory promiscuity	-	0.6857	68.57%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5817	58.17%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9385	93.85%
Skin irritation	-	0.8281	82.81%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6577	65.77%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.6140	61.40%
skin sensitisation	-	0.8359	83.59%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8916	89.16%
Acute Oral Toxicity (c)	III	0.5952	59.52%
Estrogen receptor binding	+	0.7902	79.02%
Androgen receptor binding	+	0.5841	58.41%
Thyroid receptor binding	+	0.5501	55.01%
Glucocorticoid receptor binding	+	0.6191	61.91%
Aromatase binding	+	0.7094	70.94%
PPAR gamma	+	0.7061	70.61%
Honey bee toxicity	-	0.7214	72.14%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.7808	78.08%

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	98.76%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.50%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.19%	94.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	95.22%	97.53%
CHEMBL221	P23219	Cyclooxygenase-1	94.41%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.68%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.09%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.94%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	88.24%	89.67%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.84%	89.44%
CHEMBL4208	P20618	Proteasome component C5	86.43%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.97%	99.17%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.85%	92.67%
CHEMBL3401	O75469	Pregnane X receptor	84.79%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.72%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.69%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.62%	96.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	83.38%	97.86%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.12%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.96%	94.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.56%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.39%	91.24%
CHEMBL3891	P07384	Calpain 1	82.20%	93.04%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.74%	88.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	81.60%	93.81%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.81%	93.10%
CHEMBL230	P35354	Cyclooxygenase-2	80.74%	89.63%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.31%	95.83%

Plants that contains it

• Cucurbita pepo

Cross-Links

• PubChem: 163106643
• LOTUS: LTS0001632
• wikiData: Q105343424