5-Thio-D-glucose - ≥98%(HPLC) , CAS No.20408-97-3

CAS: 20408-97-3 Cat. No.: T107913 Molecular Weight: 196.22 Beilstein Registry Number: 1865193 EC Number: 243-798-8 PubChem CID: 88527

GRADE & PURITY ≥98%(HPLC)

Synonyms

AKOS015919103 | 5-THIO-D-GLUCOSE [MI] | (2R,3R,4S,5R)-2,3,4,6-Tetrahydroxy-5-mercaptohexanal | UNII-3PRV1384UO | SCHEMBL246998 | 5-Thio-D-Glucose | alpha-D-Glucothiopyranose | AS-69032 | Q27257877 | 3PRV1384UO | AI3-63209 | (2R,3R,4S,5R)-2,3,4,6-tetrahydr

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

5-Thio-D-glucose (Glc-5S), a thiosugar hexokinase inhibitor.

Specifications

Synonyms

AKOS015919103 | 5-THIO-D-GLUCOSE [MI] | (2R, 3R, 4S, 5R)-2, 3, 4, 6-Tetrahydroxy-5-mercaptohexanal | UNII-3PRV1384UO | SCHEMBL246998 | 5-Thio-D-Glucose | alpha-D-Glucothiopyranose | AS-69032 | Q27257877 | 3PRV1384UO | AI3-63209 | (2R, 3R, 4S, 5R)-2, 3, 4, 6-tetrahydr

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Potent, competitive inhibitor of the cellular transport of D-glucose and of D-glucose mediated insulin release. Inhibitor of spermatogenesis.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504755946
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504755946
• Canonical Smiles: C(C(C(C(C(C=O)O)O)O)S)O
• IUPAC Name: (2R,3R,4S,5R)-2,3,4,6-tetrahydroxy-5-sulfanylhexanal
• InChIKey: IJJLRUSZMLMXCN-SLPGGIOYSA-N
• INCHI: 1S/C6H12O5S/c7-1-3(9)5(10)6(11)4(12)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m0/s1
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)S)O
• WGK Germany: 3
• RTECS: LZ7500000
• PubChem CID: 88527
• Molecular Weight: 196.22
• Beilstein: 1865193

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Monosaccharides
• Alternative Parents: Beta-hydroxy aldehydes Alpha-hydroxyaldehydes Secondary alcohols Polyols Alkylthiols Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Monosaccharide - Beta-hydroxy aldehyde - Alpha-hydroxyaldehyde - Secondary alcohol - Polyol - Alkylthiol - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organosulfur compound - Carbonyl group - Aldehyde - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Miscible with water.
• Specific Rotation[α]: [α]/D 220.0±5.0°, c = 1 in 0.1 M HCl
• Melt Point(°C): 135-138°C
• Molecular Weight: 196.220 g/mol
• XLogP3: -2.000
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 196.041 Da
• Monoisotopic Mass: 196.041 Da
• Topological Polar Surface Area: 99.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 142.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhenchong Xiong, Lin Yang, Chao Zhang, Weiling Huang, Wenjing Zhong, Jiarong Yi, Jikun Feng, Xiazi Zouxu, Libing Song, Xi Wang.  (2024)  MANF facilitates breast cancer cell survival under glucose-starvation conditions via prkn-mediated mitophagy regulation.  Autophagy,      [PMID:39147386] [10.1080/15548627.2024.2392415]