3,5-Dihydroxy-4-(beta-D-glucopyranosyloxy)benzoic acid methyl ester

Details

• Internal ID: 7f9ce132-2703-44e2-80f8-4e2a8bf3ceab
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: methyl 3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• SMILES (Canonical): COC(=O)C1=CC(=C(C(=C1)O)OC2C(C(C(C(O2)CO)O)O)O)O
• SMILES (Isomeric): COC(=O)C1=CC(=C(C(=C1)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• InChI: InChI=1S/C14H18O10/c1-22-13(21)5-2-6(16)12(7(17)3-5)24-14-11(20)10(19)9(18)8(4-15)23-14/h2-3,8-11,14-20H,4H2,1H3/t8-,9-,10+,11-,14+/m1/s1
• InChI Key: JUPHZGHVZWMVHU-QEGBUVANSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₁₀
• Molecular Weight: 346.29 g/mol
• Exact Mass: 346.08999677 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.94
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 3,5-Dihydroxy-4-(beta-D-glucopyranosyloxy)benzoic acid methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7149	71.49%
Caco-2	-	0.8801	88.01%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6648	66.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7451	74.51%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9349	93.49%
P-glycoprotein inhibitior	-	0.9333	93.33%
P-glycoprotein substrate	-	0.9430	94.30%
CYP3A4 substrate	-	0.5105	51.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8551	85.51%
CYP3A4 inhibition	-	0.8632	86.32%
CYP2C9 inhibition	-	0.8775	87.75%
CYP2C19 inhibition	-	0.9154	91.54%
CYP2D6 inhibition	-	0.9346	93.46%
CYP1A2 inhibition	-	0.8980	89.80%
CYP2C8 inhibition	-	0.6903	69.03%
CYP inhibitory promiscuity	-	0.7229	72.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7412	74.12%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.7887	78.87%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6801	68.01%
Micronuclear	-	0.5067	50.67%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8743	87.43%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.7019	70.19%
Acute Oral Toxicity (c)	III	0.7844	78.44%
Estrogen receptor binding	+	0.5480	54.80%
Androgen receptor binding	-	0.6678	66.78%
Thyroid receptor binding	-	0.5976	59.76%
Glucocorticoid receptor binding	+	0.6369	63.69%
Aromatase binding	-	0.5869	58.69%
PPAR gamma	-	0.5541	55.41%
Honey bee toxicity	-	0.9220	92.20%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	-	0.5277	52.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.54%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.82%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	91.10%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.89%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.16%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.36%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.31%	96.00%
CHEMBL2581	P07339	Cathepsin D	82.36%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.04%	94.33%

Plants that contains it

• Anemarrhena asphodeloides
• Carpinus cordata

Cross-Links

• PubChem: 5317705
• NPASS: NPC310661
• LOTUS: LTS0227425
• wikiData: Q105135358