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2-Deoxy-D-glucose

CAT: 0572-TRC-D239000-5GSize: 5 gDry Ice: NoHazardous: No
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CAT#:0572-TRC-D239000-5GSize:5 g
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CAS Number
154-17-6
Hazard Statement
No Data Available
Purity
>95% (HPLC)
Smiles
OC[C@@H](O)[C@@H](O)[C@H](O)CC=O
Molecular Formula
C6 H12 O5
Molecular Weight
164.16
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
Additionnal Information
IUPAC name: (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
Shipping Conditions
Room Temperature
Storage Conditions
-20°C

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