2-(beta-d-Glucopyranosyl)-3-isoxazolin-5-one

Details

• Internal ID: 20fbae1c-086b-4b24-9cd5-837f57d4a7e7
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Glycosylamines
• IUPAC Name: 2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,2-oxazol-5-one
• SMILES (Canonical): C1=CN(OC1=O)C2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): C1=CN(OC1=O)[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C9H13NO7/c11-3-4-6(13)7(14)8(15)9(16-4)10-2-1-5(12)17-10/h1-2,4,6-9,11,13-15H,3H2/t4-,6-,7+,8-,9-/m1/s1
• InChI Key: ZZWGHMOTCPPILL-DDIGBBAMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃NO₇
• Molecular Weight: 247.20 g/mol
• Exact Mass: 247.06920175 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.59
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 2-(3alpha,4beta,5alpha-Trihydroxy-6beta-(hydroxymethyl)tetrahydro-2H-pyran-2beta-yl)isoxazole-5(2H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7562	75.62%
Caco-2	-	0.8884	88.84%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5587	55.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8837	88.37%
OATP1B3 inhibitior	+	0.9425	94.25%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9371	93.71%
P-glycoprotein inhibitior	-	0.9402	94.02%
P-glycoprotein substrate	-	0.9823	98.23%
CYP3A4 substrate	-	0.6161	61.61%
CYP2C9 substrate	-	0.5891	58.91%
CYP2D6 substrate	-	0.8677	86.77%
CYP3A4 inhibition	-	0.9226	92.26%
CYP2C9 inhibition	-	0.8770	87.70%
CYP2C19 inhibition	-	0.8508	85.08%
CYP2D6 inhibition	-	0.8867	88.67%
CYP1A2 inhibition	-	0.8173	81.73%
CYP2C8 inhibition	-	0.9743	97.43%
CYP inhibitory promiscuity	-	0.8913	89.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5406	54.06%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9838	98.38%
Skin irritation	-	0.7809	78.09%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6570	65.70%
Micronuclear	+	0.7774	77.74%
Hepatotoxicity	+	0.5429	54.29%
skin sensitisation	-	0.8400	84.00%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.4690	46.90%
Acute Oral Toxicity (c)	III	0.5665	56.65%
Estrogen receptor binding	-	0.6599	65.99%
Androgen receptor binding	-	0.5540	55.40%
Thyroid receptor binding	-	0.6019	60.19%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7960	79.60%
PPAR gamma	+	0.5928	59.28%
Honey bee toxicity	-	0.9292	92.92%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.7806	78.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.43%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	84.72%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.33%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.79%	86.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.73%	91.11%

Plants that contains it

• Clausena harmandiana

Cross-Links

• PubChem: 73292443
• NPASS: NPC307978