2-Hydroxy-3-(beta-D-xylopyranosyloxy)benzoic acid

Details

• Internal ID: abd21431-e2f8-4105-9f63-b4e913632c19
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 2-hydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxybenzoic acid
• SMILES (Canonical): C1C(C(C(C(O1)OC2=CC=CC(=C2O)C(=O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=CC(=C2O)C(=O)O)O)O)O
• InChI: InChI=1S/C12H14O8/c13-6-4-19-12(10(16)9(6)15)20-7-3-1-2-5(8(7)14)11(17)18/h1-3,6,9-10,12-16H,4H2,(H,17,18)/t6-,9+,10-,12+/m1/s1
• InChI Key: LRLNKLFTNOIZNI-LYXBDTNHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₈
• Molecular Weight: 286.23 g/mol
• Exact Mass: 286.06886740 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.09
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 2-Hydroxy-3-(beta-D-xylopyranosyloxy)benzoic acid
• 2,3-DHBA 3-O-Xyl
• CHEBI:91166
• Q27163102

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5371	53.71%
Caco-2	-	0.8803	88.03%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6325	63.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9594	95.94%
OATP1B3 inhibitior	+	0.8414	84.14%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9553	95.53%
P-glycoprotein inhibitior	-	0.9533	95.33%
P-glycoprotein substrate	-	0.8784	87.84%
CYP3A4 substrate	-	0.5673	56.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.9162	91.62%
CYP2C9 inhibition	-	0.9264	92.64%
CYP2C19 inhibition	-	0.9533	95.33%
CYP2D6 inhibition	-	0.9187	91.87%
CYP1A2 inhibition	-	0.9145	91.45%
CYP2C8 inhibition	+	0.4601	46.01%
CYP inhibitory promiscuity	-	0.9050	90.50%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6965	69.65%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.5626	56.26%
Skin irritation	-	0.7353	73.53%
Skin corrosion	-	0.9494	94.94%
Ames mutagenesis	-	0.5023	50.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.7771	77.71%
Micronuclear	+	0.6492	64.92%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7714	77.14%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7698	76.98%
Acute Oral Toxicity (c)	III	0.7168	71.68%
Estrogen receptor binding	-	0.5345	53.45%
Androgen receptor binding	-	0.7535	75.35%
Thyroid receptor binding	-	0.5437	54.37%
Glucocorticoid receptor binding	-	0.5140	51.40%
Aromatase binding	-	0.6480	64.80%
PPAR gamma	+	0.6171	61.71%
Honey bee toxicity	-	0.8875	88.75%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8150	81.50%
Fish aquatic toxicity	+	0.6763	67.63%

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	96.02%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.52%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.28%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.33%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL2581	P07339	Cathepsin D	85.63%	98.95%
CHEMBL3194	P02766	Transthyretin	83.76%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.06%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.69%	95.89%
CHEMBL2535	P11166	Glucose transporter	82.02%	98.75%
CHEMBL3891	P07384	Calpain 1	81.62%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.55%	97.09%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 101524168
• LOTUS: LTS0054760
• wikiData: Q27163102