[(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 4-hydroxybenzoate

Details

• Internal ID: a80e3e8e-2342-4f10-83eb-3b4e343814d6
• 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 4-hydroxybenzoate
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=CC=C(C=C3)CCO)CO)O)O)O)(COC(=O)C4=CC=C(C=C4)O)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=C(C=C4)O)O
• InChI: InChI=1S/C26H32O13/c27-10-9-14-1-7-17(8-2-14)37-24-21(20(31)19(30)18(11-28)38-24)39-25-22(32)26(34,13-36-25)12-35-23(33)15-3-5-16(29)6-4-15/h1-8,18-22,24-25,27-32,34H,9-13H2/t18-,19-,20+,21-,22+,24-,25+,26-/m1/s1
• InChI Key: AYLSGEWHCBDIDG-JUKYQPCLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₃
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.18429107 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.56
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7337	73.37%
Caco-2	-	0.8984	89.84%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7885	78.85%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.8777	87.77%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5836	58.36%
P-glycoprotein inhibitior	-	0.5243	52.43%
P-glycoprotein substrate	-	0.5819	58.19%
CYP3A4 substrate	+	0.6803	68.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.8661	86.61%
CYP2C9 inhibition	-	0.8372	83.72%
CYP2C19 inhibition	-	0.8671	86.71%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	-	0.9136	91.36%
CYP2C8 inhibition	+	0.7865	78.65%
CYP inhibitory promiscuity	-	0.8475	84.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5542	55.42%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9106	91.06%
Skin irritation	-	0.8163	81.63%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6959	69.59%
Micronuclear	-	0.6767	67.67%
Hepatotoxicity	-	0.7445	74.45%
skin sensitisation	-	0.8726	87.26%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7794	77.94%
Acute Oral Toxicity (c)	III	0.6551	65.51%
Estrogen receptor binding	+	0.7902	79.02%
Androgen receptor binding	+	0.6771	67.71%
Thyroid receptor binding	-	0.5250	52.50%
Glucocorticoid receptor binding	+	0.5637	56.37%
Aromatase binding	+	0.6904	69.04%
PPAR gamma	+	0.6638	66.38%
Honey bee toxicity	-	0.6928	69.28%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7350	73.50%
Fish aquatic toxicity	-	0.4860	48.60%

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	98.36%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.12%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.00%	97.09%
CHEMBL3437	Q16853	Amine oxidase, copper containing	95.41%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.41%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.34%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.58%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.91%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.38%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.65%	95.89%
CHEMBL4208	P20618	Proteasome component C5	89.52%	90.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	89.30%	94.97%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	88.32%	85.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.17%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.17%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.53%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.19%	94.62%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	82.44%	96.69%
CHEMBL3232685	O00257	E3 SUMO-protein ligase CBX4	82.00%	93.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.86%	94.33%
CHEMBL2514	O95665	Neurotensin receptor 2	81.71%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.19%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.04%	91.19%
CHEMBL2581	P07339	Cathepsin D	80.41%	98.95%

Plants that contains it

• Bryonia alba
• Cucurbita moschata

Cross-Links

• PubChem: 11444250
• NPASS: NPC74181
• LOTUS: LTS0018885
• wikiData: Q104921202