[(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-aminobenzoate

Details

• Internal ID: 1fca8534-066c-4bae-9e03-ac516ef06f31
• 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-aminobenzoate
• 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)N)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)N)O
• InChI: InChI=1S/C26H33NO12/c27-16-5-3-15(4-6-16)23(33)35-12-26(34)13-36-25(22(26)32)39-21-20(31)19(30)18(11-29)38-24(21)37-17-7-1-14(2-8-17)9-10-28/h1-8,18-22,24-25,28-32,34H,9-13,27H2/t18-,19-,20+,21-,22+,24-,25+,26-/m1/s1
• InChI Key: ACOKXVSLVQCZRD-JUKYQPCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₃NO₁₂
• Molecular Weight: 551.50 g/mol
• Exact Mass: 551.20027549 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.69
• 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	-	0.7963	79.63%
Caco-2	-	0.8851	88.51%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.3988	39.88%
OATP2B1 inhibitior	-	0.8532	85.32%
OATP1B1 inhibitior	+	0.9068	90.68%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6543	65.43%
P-glycoprotein inhibitior	-	0.4683	46.83%
P-glycoprotein substrate	-	0.5431	54.31%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8219	82.19%
CYP3A4 inhibition	-	0.9221	92.21%
CYP2C9 inhibition	-	0.8194	81.94%
CYP2C19 inhibition	-	0.7684	76.84%
CYP2D6 inhibition	-	0.8819	88.19%
CYP1A2 inhibition	-	0.8487	84.87%
CYP2C8 inhibition	+	0.6290	62.90%
CYP inhibitory promiscuity	-	0.8140	81.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5184	51.84%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.7947	79.47%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6684	66.84%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.7570	75.70%
skin sensitisation	-	0.8372	83.72%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8801	88.01%
Acute Oral Toxicity (c)	III	0.6122	61.22%
Estrogen receptor binding	+	0.7619	76.19%
Androgen receptor binding	+	0.7122	71.22%
Thyroid receptor binding	-	0.5063	50.63%
Glucocorticoid receptor binding	+	0.5806	58.06%
Aromatase binding	+	0.6737	67.37%
PPAR gamma	+	0.6877	68.77%
Honey bee toxicity	-	0.7241	72.41%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	-	0.6066	60.66%

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	99.29%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.27%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.71%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.93%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.71%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.67%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.11%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.03%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.05%	99.17%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	89.00%	95.48%
CHEMBL4208	P20618	Proteasome component C5	88.64%	90.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	87.71%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.76%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.42%	94.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.28%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.44%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.25%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.88%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.51%	86.92%
CHEMBL3891	P07384	Calpain 1	80.05%	93.04%

Plants that contains it

• Cucurbita pepo

Cross-Links

• PubChem: 11555787
• LOTUS: LTS0268464
• wikiData: Q104909212