2-Deoxy-D-glucose, glucose analog

Key facts

CAS number

61-58-5

Purity

>97%

Form

Solid

form

Molecular weight

164.16 Da

Molecular formula

C₆H₁₂O₅

PubChem

439268

Nature

Synthetic

Solubility

Soluble in Water >15 mg/mL

Soluble in DMSO >15 mg/mL.

Biochemical name

2-Deoxy-D-arabino-hexopyranose

Biological description

Non-metabolizable glucose analog and glycolytic inhibitor. Competitive phosphoglucose isomerase inhibitor. Induces ROS-dependent autophagy (EC₅₀ = 100 μM) and depletes cellular ATP. Antitumor and antiproliferative activity in vivo and in vitro. Orally active.

Canonical smiles

C1C(C(C(OC1O)CO)O)O

Isomeric smiles

C1[C@H]([C@@H]([C@H](OC1O)CO)O)O

InChi

InChI=1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6+/m1/s1

InChiKey

PMMURAAUARKVCB-CERMHHMHSA-N

IUPAC Name

(4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol