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2-Deoxy-D-glucose

CAT: 0804-HY-13966-01Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13966-01Size:500 mg
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Description
2-Deoxy-D-glucose is a glucose analog that acts as a competitive inhibitor of glucose metabolism, inhibiting glycolysis via its actions on hexokinase[1].
CAS Number
154-17-6
Product Name Alternative
2-DG; 2-Deoxy-D-arabino-hexose; D-Arabino-2-deoxyhexose
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Hexokinase; HSV
Type
Natural Products
Related Pathways
Anti-infection; Apoptosis; Metabolic Enzyme/Protease
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/2-Deoxy-D-glucose.html
Purity
99.93
Solubility
H2O : 125 mg/mL (ultrasonic)
Smiles
OC1O[C@@H]([C@@H](O)[C@H](O)C1)CO
Molecular Formula
C6H12O5
Molecular Weight
164.16
Precautions
H302, H315, H319, H335
References & Citations
[1]Zhu Z, et al. 2-Deoxyglucose as an energy restriction mimetic agent: effects on mammary carcinogenesis and on mammary tumor cell growth in vitro. Cancer Res. 2005 Aug 1;65 (15) :7023-30.|[2]Ueyama A, et al. Nonradioisotope assay of glucose uptake activity in rat skeletal muscle using enzymatic measurement of 2-deoxyglucose 6-phosphate in vitro and in vivo. Biol Signals Recept. 2000 Sep-Oct;9 (5) :267-74.|[3]Miwa H, et al. Leukemia cells demonstrate a different metabolic perturbation provoked by 2-deoxyglucose. Oncol Rep. 2013 May;29 (5) :2053-7.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
Phase 2
Isoform
HSV-1

Chemical Information

2-Deoxyglucose

2-deoxyglucose is predominantly used as a diagnostic agent in its radiolabelled form (fluorine-18 is used as the radiolabel). By using positron emission tomography (PET), radiolabelled 2-deoxyglucose can determine glucose metabolism, which is altered in diseases such as cardiovascular disease, tumors, and Alzheimer's disease. Therapeutically, 2-deoxyglucose is an investigational drug that is being studied as an anticancer and antiviral agent. Concerning the former, 2- deoxyglucose was used as an adjunct to chemotherapy and radiotherapy in the treatment of solid tumors (lung, breast, pancreas, head, neck, and gastric tumors). The exact mechanisms of action of 2-deoxyglucose is still being investigated, but it is known that in hypoxic cancer cells, 2-deoxyglucose is a glycolysis inhibitor that prevents ATP production and, ultimately, cell survival. With respect to antiviral therapy, 2-deoxyglucose was shown to be effective against herpes simplex virus by affecting the virus' ability to penetrate cells. As an experimental drug, 2-deoxyglucose was demonstrated to work as an anticonvulsant in temporal lobe epilepsy. In this condition, 2-deoxyglucose represses the expression of certain proteins that are at high levels after a seizure. Although there are several possible therapeutic indications for 2-deoxyglucose, presently there is no approved indication for 2-deoxyglucose as a therapeutic agent.

CAS Number154-17-6
PubChem CID108223
IUPAC Name(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
Molecular FormulaC6H12O5
Molecular Weight164.16
XLogP-2.9
Topological Polar Surface Area98
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Heavy Atom Count11
Formal Charge0
Complexity116
SMILES
C(C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
InChI
InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1
InChIKey
VRYALKFFQXWPIH-PBXRRBTRSA-N
Chemical Structure
2D Structure
2D structure of 2-Deoxyglucose
CAS: 154-17-6
CID: 108223
Formula: C6H12O5
MW: 164.16
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight164.16
XLogP3-2.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass164.06847348
Monoisotopic Mass164.06847348
Topological Polar Surface Area98 Ų
Heavy Atom Count11
Formal Charge0
Complexity116
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes