(2S,3R,4S,5S,6R)-6-(hydroxymethyl)thiane-2,3,4,5-tetrol

• ChemBase ID: 137101
• Molecular Formular: C6H12O5S
• Molecular Mass: 196.22148
• Monoisotopic Mass: 196.04054448
• SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](S1)O)O)O)O)O
• Canonical SMILES: OC[C@H]1S[C@H](O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H12O5S/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1
• InChIKey: KNWYARBAEIMVMZ-DVKNGEFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-6-(hydroxymethyl)thiane-2,3,4,5-tetrol
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-6-(hydroxymethyl)thiane-2,3,4,5-tetrol
• Synonyms: 5-Thio-D-glucose

Database IDs

• CAS Number: 20408-97-3
• EC Number: 243-798-8
• MDL Number: MFCD00006663
• Beilstein Number: 1865193
• PubChem SID: 24888492; 24888977; 162231366
• PubChem CID: 5288443

CALCULATED PROPERTIES

• Acid pKa: 12.410834
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -2.6214085
• LogD (pH = 7.4): -2.6214125
• Log P: -2.6214085
• Molar Refractivity: 42.2742 cm^3
• Polarizability: 17.435747 Å^3
• Polar Surface Area: 101.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 135-138 °C(lit.)
• Optical Rotation: [α]/D 220.0±5.0°, c = 1 in 0.1 M HCl; [α]20/D +224°, c = 1 in 0.1 M HCl

Safety Information

• RTECS: LZ7500000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 96%
• Empirical Formula (Hill Notation): C6H12O5S

DETAILS

Sigma Aldrich - 88635

Biochem/physiol Actions
Potent, competitive inhibitor of the cellular transport of D-glucose and of D-glucose mediated insulin release.1,2 Inhibitor of spermatogenesis.3
Packaging
1 g in poly tube
Application
5-Thio-D-glucose (Glc-5S), a thiosugar hexokinase inhibitor, is used to control/reduce the rate of glycolysis in vivo.