1-O-(2-hydroxybenzoyl)-D-glucopyranose

Details

• Internal ID: a4cd99b2-fc22-43e6-b4cc-50b494b9f74e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Hexoses
• IUPAC Name: [(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-hydroxybenzoate
• SMILES (Canonical): C1=CC=C(C(=C1)C(=O)OC2C(C(C(C(O2)CO)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C(=C1)C(=O)OC2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• InChI: InChI=1S/C13H16O8/c14-5-8-9(16)10(17)11(18)13(20-8)21-12(19)6-3-1-2-4-7(6)15/h1-4,8-11,13-18H,5H2/t8-,9-,10+,11-,13?/m1/s1
• InChI Key: XNHKMZHWRNMFCU-TWEVDUBQSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₈
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.08451746 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.65
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 1-O-salicyl-D-glucose
• salicylate-D-glucose ester
• SCHEMBL4652290
• CHEBI:133564
• 1-O-(2-hydroxybenzoyl)-D-glucose
• 1-O-(2-hydroxybenzoyl)-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7179	71.79%
Caco-2	-	0.8846	88.46%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6547	65.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8900	89.00%
OATP1B3 inhibitior	+	0.9117	91.17%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9875	98.75%
P-glycoprotein inhibitior	-	0.9527	95.27%
P-glycoprotein substrate	-	0.9814	98.14%
CYP3A4 substrate	-	0.5390	53.90%
CYP2C9 substrate	-	0.8109	81.09%
CYP2D6 substrate	-	0.8580	85.80%
CYP3A4 inhibition	-	0.8778	87.78%
CYP2C9 inhibition	-	0.8645	86.45%
CYP2C19 inhibition	-	0.9316	93.16%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	-	0.9387	93.87%
CYP2C8 inhibition	-	0.6669	66.69%
CYP inhibitory promiscuity	-	0.7465	74.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7410	74.10%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.6952	69.52%
Skin irritation	-	0.8020	80.20%
Skin corrosion	-	0.9703	97.03%
Ames mutagenesis	-	0.7570	75.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7946	79.46%
Micronuclear	-	0.5208	52.08%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.7932	79.32%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7436	74.36%
Acute Oral Toxicity (c)	III	0.6875	68.75%
Estrogen receptor binding	-	0.6859	68.59%
Androgen receptor binding	-	0.6842	68.42%
Thyroid receptor binding	-	0.5127	51.27%
Glucocorticoid receptor binding	-	0.6411	64.11%
Aromatase binding	-	0.6420	64.20%
PPAR gamma	+	0.5652	56.52%
Honey bee toxicity	-	0.8816	88.16%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	-	0.3649	36.49%

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	98.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.89%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.01%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.08%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.97%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.63%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.36%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.44%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.00%	96.61%

Plants that contains it

• Nicotiana tabacum

Cross-Links

• PubChem: 54478488
• LOTUS: LTS0130300
• wikiData: Q104400615