2-(Beta-D-Glucopyranosyl)-5-Methyl-1,3,4-Oxadiazole

Identification

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Name
2-(Beta-D-Glucopyranosyl)-5-Methyl-1,3,4-Oxadiazole
Accession Number
DB03354  (EXPT02455)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 246.2173
Monoisotopic: 246.08518619
Chemical Formula
C9H14N2O6
InChI Key
HCSFWJQLIPWUFZ-JAJWTYFOSA-N
InChI
InChI=1S/C9H14N2O6/c1-3-10-11-9(16-3)8-7(15)6(14)5(13)4(2-12)17-8/h4-8,12-15H,2H2,1H3/t4-,5-,6+,7-,8-/m1/s1
IUPAC Name
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(5-methyl-1,3,4-oxadiazol-2-yl)oxane-3,4,5-triol
SMILES
[H][C@]1(CO)O[C@@]([H])(C2=NN=C(C)O2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, muscle formNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
657043
PubChem Substance
46506713
ChemSpider
571261
BindingDB
50295847
ChEBI
44722
ChEMBL
CHEMBL540929
HET
OX2
PDB Entries
1xl0

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility48.7 mg/mLALOGPS
logP-1.6ALOGPS
logP-3.5ChemAxon
logS-0.7ALOGPS
pKa (Strongest Acidic)12.4ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.94 m3·mol-1ChemAxon
Polarizability22.59 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9909
Blood Brain Barrier+0.6623
Caco-2 permeable-0.7639
P-glycoprotein substrateNon-substrate0.7594
P-glycoprotein inhibitor INon-inhibitor0.9193
P-glycoprotein inhibitor IINon-inhibitor0.9868
Renal organic cation transporterNon-inhibitor0.9303
CYP450 2C9 substrateNon-substrate0.8072
CYP450 2D6 substrateNon-substrate0.8211
CYP450 3A4 substrateNon-substrate0.5332
CYP450 1A2 substrateNon-inhibitor0.8148
CYP450 2C9 inhibitorNon-inhibitor0.8884
CYP450 2D6 inhibitorNon-inhibitor0.9564
CYP450 2C19 inhibitorNon-inhibitor0.8335
CYP450 3A4 inhibitorNon-inhibitor0.895
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9458
Ames testNon AMES toxic0.5588
CarcinogenicityNon-carcinogens0.9104
BiodegradationNot ready biodegradable0.8423
Rat acute toxicity2.1311 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9896
hERG inhibition (predictor II)Non-inhibitor0.94
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
C-glycosyl compounds
Alternative Parents
Oxanes / Monosaccharides / Heteroaromatic compounds / 1,3,4-oxadiazoles / Secondary alcohols / Polyols / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Primary alcohols
show 3 more
Substituents
C-glycosyl compound / Monosaccharide / Oxane / 1,3,4-oxadiazole / Azole / Heteroaromatic compound / Oxadiazole / Secondary alcohol / Dialkyl ether / Ether
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
C-glycosyl compound, 1,3,4-oxadiazole (CHEBI:44722)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:49