CHEBI:15866 - 2-deoxy-D-glucose

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ChEBI Name 2-deoxy-D-glucose
ChEBI ID CHEBI:15866
ChEBI ASCII Name 2-deoxy-D-glucose
Definition A deoxyglucose that is D-glucose in which the hydroxy group at position 2 has been replaced by a hydrogen. It is an antimetabolite of glucose with antiviral activity, which acts by inhibiting the glycosylation of glycoproteins and glycolipids. Used as an antiherpes agent.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:11569, CHEBI:19553, CHEBI:11565, CHEBI:1078, CHEBI:57546
Wikipedia License
2-Deoxy-d-glucose is a glucose molecule which has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. As such; it acts to competitively inhibit the production of glucose-6-phosphate from glucose at the phosphoglucoisomerase level (step 2 of glycolysis). 2-Deoxyglucose labeled with tritium or carbon-14 has been a popular ligand for laboratory research in animal models, where distribution is assessed by tissue-slicing followed by autoradiography, sometimes in tandem with either conventional or electron microscopy. 2-DG is up taken by the glucose transporters of the cell. Therefore, cells with higher glucose uptake, for example tumor cells, have also a higher uptake of 2-DG. Since 2-DG hampers cell growth, its use as a tumor therapeutic has been suggested, and in fact, 2-DG is in clinical trials. It is not completely clear how 2-DG inhibits cell growth. The fact that glycolysis is inhibited by 2-DG, seems not to be sufficient to explain why 2-DG treated cells stop growing. A synergistic effect between 2-DG and various other agents have been reported in the pursuit of anticancer strategies. Because of its structural similarity to mannose, 2DG has the potential to inhibit N-glycosylation in mammalian cells and other systems, and as such induces ER stress and the Unfolded Protein Response (UPR) pathway.
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Formula C6H12O5
Net Charge 0
Average Mass 164.15650
Monoisotopic Mass 164.06847
Roles Classification
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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ChEBI Ontology
Outgoing 2-deoxy-D-glucose (CHEBI:15866) has functional parent D-glucopyranose (CHEBI:4167)
2-deoxy-D-glucose (CHEBI:15866) has functional parent D-glucose (CHEBI:17634)
2-deoxy-D-glucose (CHEBI:15866) has role geroprotector (CHEBI:176497)
2-deoxy-D-glucose (CHEBI:15866) is a deoxyglucose (CHEBI:23623)
Incoming 2-deoxy-D-glucopyranose (CHEBI:84755) is a 2-deoxy-D-glucose (CHEBI:15866)
IUPAC Name
2-deoxy-D-arabino-hexose
Synonyms Sources
2-Deoxy-D-arabino-hexose KEGG COMPOUND
2-Deoxy-D-glucose KEGG COMPOUND
2-Deoxy-D-mannose ChemIDplus
D-2dGlc JCBN
D-arabino-2-Deoxyhexose KEGG COMPOUND
Deoxyglucose ChemIDplus
Manual Xrefs Databases
2-Deoxy-D-glucose Wikipedia
2-DEOXY-D-GLUCOSE MetaCyc
C00586 KEGG COMPOUND
View more database links
Registry Number Type Source
154-17-6 CAS Registry Number KEGG COMPOUND
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Last Modified
20 September 2021