MiMeDB: Showing metabocard for 2-deoxy-D-glucose (MMDBc0054165)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:56:42 UTC

Update Date

2025-10-07 16:08:24 UTC

Metabolite ID

MMDBc0054165

Metabolite Identification

Common Name

2-deoxy-D-glucose

Description

2-deoxy-D-glucose is a synthetic glucose analog belonging to the class of carbohydrate metabolites. Its chemical structure is characterized by the absence of a hydroxyl group at the 2-position of the glucose molecule, which alters its metabolic pathways. 2-deoxy-D-glucose is primarily involved in glycolysis, where it competes with glucose for uptake and phosphorylation, leading to the production of 2-deoxy-D-glucose-6-phosphate, which cannot proceed through the glycolytic pathway. This inhibition of glycolysis has been shown to have significant effects on cellular metabolism and function; for instance, Co2+-induced enhancement of glycolysis and cytokine secretion was significantly reduced when cells were treated with 2-deoxy-D-glucose, indicating its role in modulating metabolic responses (PMID:41036386 ). Additionally, 2-deoxy-D-glucose is utilized in imaging techniques, such as positron emission tomography (PET), where its fluorinated derivative, 18F-2-Fluoro-2-deoxy-D-glucose ([18F]FDG), serves as a crucial molecular probe for tumor detection in clinical settings (PMID:41036744 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Deoxy-D-glucose	ChEBI
2-Deoxy-D-mannopyranose	ChEBI
2-Deoxyglucopyranose	ChEBI
2-Deoxymannopyranose	ChEBI
2 Deoxy D glucose	MeSH
2 Desoxy D glucose	MeSH
2 Deoxyglucose	MeSH
2-Desoxy-D-glucose	MeSH
Deoxyglucose	MeSH

Molecular Formula

C₆H₁₂O₅

Average Mass

164.1565

Monoisotopic Mass

164.068473494

IUPAC Name

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

Traditional Name

2-deoxy-D-glucose

CAS Registry Number

Not Available

SMILES

OC[C@H]1OC(O)C[C@@H](O)[C@@H]1O

InChI Identifier

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

InChI Key

PMMURAAUARKVCB-CERMHHMHSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

2-deoxy-D-glucose (CHEBI:84755 )
Deoxy sugars (C00586 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	984 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2	ChemAxon
logS	0.78	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.41 m³·mol⁻¹	ChemAxon
Polarizability	15.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	308.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	218.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	48.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	232.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	262.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	281.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	743.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	619.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	680.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	154.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	310.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	171.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	50.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	303.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	566.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	52.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	181.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	805.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	557.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	2-deoxy-D-glucose_TMS_1	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@@H]1O	standard non polar	2025-10-24	1999.31
Gas Chromatography	2-deoxy-D-glucose_TMS_2	C[Si](C)(C)OC1C[C@@H](O)[C@H](O)[C@@H](CO)O1	standard non polar	2025-10-24	1825.14
Gas Chromatography	2-deoxy-D-glucose_TMS_3	C[Si](C)(C)O[C@@H]1CC(O)O[C@H](CO)[C@H]1O	standard non polar	2025-10-24	2002.0
Gas Chromatography	2-deoxy-D-glucose_TMS_4	C[Si](C)(C)O[C@H]1[C@H](O)CC(O)O[C@@H]1CO	standard non polar	2025-10-24	1978.7
Gas Chromatography	2-deoxy-D-glucose_TMS_5	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O)[C@@H]1O	standard non polar	2025-10-24	1836.3
Gas Chromatography	2-deoxy-D-glucose_TMS_6	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-24	2057.53
Gas Chromatography	2-deoxy-D-glucose_TMS_7	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2114.31
Gas Chromatography	2-deoxy-D-glucose_TMS_8	C[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO)O1	standard non polar	2025-10-24	1529.27
Gas Chromatography	2-deoxy-D-glucose_TMS_9	C[Si](C)(C)OC1C[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO)O1	standard non polar	2025-10-24	1944.51
Gas Chromatography	2-deoxy-D-glucose_TMS_10	C[Si](C)(C)O[C@@H]1CC(O)O[C@H](CO)[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2105.81
Gas Chromatography	2-deoxy-D-glucose_TMS_11	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-24	1806.77
Gas Chromatography	2-deoxy-D-glucose_TMS_12	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2068.2
Gas Chromatography	2-deoxy-D-glucose_TMS_13	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1441.14
Gas Chromatography	2-deoxy-D-glucose_TMS_14	C[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO)O1	standard non polar	2025-10-24	838.103
Gas Chromatography	2-deoxy-D-glucose_TMS_15	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2030.34
Gas Chromatography	2-deoxy-D-glucose_TMS_1	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@@H]1O	standard polar	2025-10-24	1874.31
Gas Chromatography	2-deoxy-D-glucose_TMS_2	C[Si](C)(C)OC1C[C@@H](O)[C@H](O)[C@@H](CO)O1	standard polar	2025-10-24	2524.15
Gas Chromatography	2-deoxy-D-glucose_TMS_3	C[Si](C)(C)O[C@@H]1CC(O)O[C@H](CO)[C@H]1O	standard polar	2025-10-24	2396.12
Gas Chromatography	2-deoxy-D-glucose_TMS_4	C[Si](C)(C)O[C@H]1[C@H](O)CC(O)O[C@@H]1CO	standard polar	2025-10-24	1762.63
Gas Chromatography	2-deoxy-D-glucose_TMS_5	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O)[C@@H]1O	standard polar	2025-10-24	1949.85
Gas Chromatography	2-deoxy-D-glucose_TMS_6	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-24	1674.79
Gas Chromatography	2-deoxy-D-glucose_TMS_7	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	2063.42
Gas Chromatography	2-deoxy-D-glucose_TMS_8	C[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](CO)O1	standard polar	2025-10-24	2689.91
Gas Chromatography	2-deoxy-D-glucose_TMS_9	C[Si](C)(C)OC1C[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](CO)O1	standard polar	2025-10-24	2165.79
Gas Chromatography	2-deoxy-D-glucose_TMS_10	C[Si](C)(C)O[C@@H]1CC(O)O[C@H](CO)[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	2604.05
Gas Chromatography	2-deoxy-D-glucose_TMS_11	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-24	2688.48
Gas Chromatography	2-deoxy-D-glucose_TMS_12	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	2421.72
Gas Chromatography	2-deoxy-D-glucose_TMS_13	C[Si](C)(C)OC[C@H]1OC(O)C[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	2274.23
Gas Chromatography	2-deoxy-D-glucose_TMS_14	C[Si](C)(C)OC1C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](CO)O1	standard polar	2025-10-24	2366.93
Gas Chromatography	2-deoxy-D-glucose_TMS_15	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-24	2280.53

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	2

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB08831

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00586

BioCyc ID

2-DEOXY-D-GLUCOSE

BiGG ID

Not Available

Wikipedia Link

2-Deoxy-D-glucose

METLIN ID

Not Available

PubChem Compound

439268

PDB ID

Not Available

ChEBI ID

84755

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2-deoxy-D-glucose (MMDBc0054165)

MOL for #<Metabolite:0x00005643230d40a0>

3D MOL for #<Metabolite:0x00005643230d40a0>

3D SDF for #<Metabolite:0x00005643230d40a0>

3D-SDF for #<Metabolite:0x00005643230d40a0>

PDB for #<Metabolite:0x00005643230d40a0>

3D PDB for #<Metabolite:0x00005643230d40a0>

SMILES for #<Metabolite:0x00005643230d40a0>

INCHI for #<Metabolite:0x00005643230d40a0>

Structure for #<Metabolite:0x00005643230d40a0>

3D Structure for #<Metabolite:0x00005643230d40a0>