Pyrocatechol monoglucoside

Details

• Internal ID: 0dcf5e37-6f65-478f-89ce-6bac9d9942fd
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-hydroxyphenoxy)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC=C(C(=C1)O)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): C1=CC=C(C(=C1)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-4-2-1-3-6(7)14/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
• InChI Key: NMZWIAATAZXMRV-RMPHRYRLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆O₇
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.08960285 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 2400-71-7
• (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-hydroxyphenoxy)oxane-3,4,5-triol
• Pyrocatecholmonoglucoside
• o-Hydroxyphenyl -D-glucoside
• SCHEMBL166162
• CHEMBL443206
• HY-N1577
• AKOS040762253
• FS-9331
• 2-methoxyphenyl-I(2)-D-glucopyranoside
• CS-0017126
• (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(2-hydroxyphenoxy)-tetrahydro-2h-pyran-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8070	80.70%
Caco-2	-	0.8349	83.49%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6140	61.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9421	94.21%
OATP1B3 inhibitior	+	0.9298	92.98%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9857	98.57%
P-glycoprotein inhibitior	-	0.9587	95.87%
P-glycoprotein substrate	-	0.9779	97.79%
CYP3A4 substrate	-	0.5956	59.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.8961	89.61%
CYP2C9 inhibition	-	0.8385	83.85%
CYP2C19 inhibition	-	0.8758	87.58%
CYP2D6 inhibition	-	0.9274	92.74%
CYP1A2 inhibition	-	0.9361	93.61%
CYP2C8 inhibition	-	0.7430	74.30%
CYP inhibitory promiscuity	-	0.6931	69.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6813	68.13%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.7555	75.55%
Skin irritation	-	0.8183	81.83%
Skin corrosion	-	0.9658	96.58%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7749	77.49%
Micronuclear	-	0.5582	55.82%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.7840	78.40%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.5934	59.34%
Acute Oral Toxicity (c)	III	0.6952	69.52%
Estrogen receptor binding	-	0.7825	78.25%
Androgen receptor binding	-	0.7309	73.09%
Thyroid receptor binding	-	0.5248	52.48%
Glucocorticoid receptor binding	-	0.6110	61.10%
Aromatase binding	-	0.7583	75.83%
PPAR gamma	+	0.5288	52.88%
Honey bee toxicity	-	0.8711	87.11%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.4555	45.55%

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	98.36%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.01%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.30%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.10%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.70%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.98%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.69%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.38%	86.33%

Plants that contains it

• Itoa orientalis
• Salix babylonica

Cross-Links

• PubChem: 9900144
• LOTUS: LTS0200394
• wikiData: Q105182029