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NAG-thiazoline

CAT: 0804-HY-139431-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-139431-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
NAG-thiazoline is a O-GlcNAcase inhibitor with a Ki of 180 nM. NAG-thiazoline is a potent GH20 GlcNAcase (VhGlcNAcase) inhibitor with an IC50 of 11.9 μM and a Ki of 62 µM[1].
CAS Number
179030-22-9
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Bacterial; OGA
Type
Reference compound
Related Pathways
Anti-infection; Neuronal Signaling
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/nag-thiazoline.html
Purity
98.08
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O[C@@H]1[C@]2([H])[C@](SC(C)=N2)([H])O[C@@H]([C@H]1O)CO
Molecular Formula
C8H13NO4S
Molecular Weight
219.26
Precautions
H302, H315, H319, H335
References & Citations
[1]Macauley MS, et al. Increasing O-GlcNAc levels: An overview of small-molecule inhibitors of O-GlcNAcase. Biochim Biophys Acta. 2010 Feb;1800 (2) :107-21. |[2]Piyanat Meekrathok, et al. NAG-thiazoline is a potent inhibitor of the Vibrio campbellii GH20 β-N-Acetylglucosaminidase. FEBS J. 2020 Nov;287 (22) :4982-4995.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

N-Acetyl-glucosamine thiazoline

N-Acetyl-glucosamine thiazoline (NAG-thiazoline) is an analog of the oxazolinium bicyclic intermediate leading from N-acetylglucosamine to 1,6-anhydro-N-acetylmuramic acid.

CAS Number179030-22-9
PubChem CID5289024
IUPAC Name(3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
Molecular FormulaC8H13NO4S
Molecular Weight219.26
XLogP-1.1
Topological Polar Surface Area108
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Heavy Atom Count14
Formal Charge0
Complexity260
SMILES
CC1=N[C@@H]2[C@H]([C@@H]([C@H](O[C@@H]2S1)CO)O)O
InChI
InChI=1S/C8H13NO4S/c1-3-9-5-7(12)6(11)4(2-10)13-8(5)14-3/h4-8,10-12H,2H2,1H3/t4-,5-,6-,7-,8-/m1/s1
InChIKey
DRHXTSWSUAJOJZ-FMDGEEDCSA-N
Chemical Structure
2D Structure
2D structure of N-Acetyl-glucosamine thiazoline
CAS: 179030-22-9
CID: 5289024
Formula: C8H13NO4S
MW: 219.26
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight219.26
XLogP3-1.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Exact Mass219.05652907
Monoisotopic Mass219.05652907
Topological Polar Surface Area108 Ų
Heavy Atom Count14
Formal Charge0
Complexity260
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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