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2-Deoxy-D-galactose

PubChem CID
102191
Structure
2-Deoxy-D-galactose_small.png
2-Deoxy-D-galactose_3D_Structure.png
Molecular Formula
Synonyms
  • 2-Deoxy-D-galactose
  • 1949-89-9
  • D-lyxo-Hexose, 2-deoxy-
  • (3R,4R,5R)-3,4,5,6-tetrahydroxyhexanal
  • lyxo-Hexose, 2-deoxy-
Molecular Weight
164.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
2-deoxy-D-galactose is a deoxygalactose. It is functionally related to an aldehydo-D-galactose and a D-galactose.
2-Deoxy-D-glucose is a non-metabolizable glucose analog in which the hydroxyl group at position 2 of glucose is replaced by hydrogen, with potential glycolysis inhibiting and antineoplastic activities. Although the exact mechanism of action has yet to be fully elucidated, upon administration of 2-deoxy-D-glucose (2-DG), this agent competes with glucose for uptake by proliferating cells, such as tumor cells. 2-DG inhibits the first step of glycolysis and therefore prevents cellular energy production, which may result in decreased tumor cell proliferation.
See also: 2-Deoxy-lyxo-hexose (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-Deoxy-D-galactose.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
2-deoxy-aldehydo-D-lyxHex
LINUCS
[][2-deoxy-aldehydo-D-lyxHex]{}
IUPAC
2-deoxy-aldehydo-D-lyxo-hexose

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(3R,4R,5R)-3,4,5,6-tetrahydroxyhexanal
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

VRYALKFFQXWPIH-HSUXUTPPSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C(C=O)[C@H]([C@H]([C@@H](CO)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C6H12O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

6664-99-9
154-17-6

3.3.2 Deprecated CAS

25494-04-6

3.3.3 European Community (EC) Number

3.3.4 UNII

3.3.5 ChEBI ID

3.3.6 DSSTox Substance ID

3.3.7 Metabolomics Workbench ID

3.3.8 NCI Thesaurus Code

3.3.9 Nikkaji Number

3.3.10 Wikidata

3.3.11 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 2-deoxy-D-galactose
  • 2-deoxy-lyxo-hexose
  • 2-deoxy-lyxo-hexose, (D)-isomer

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
164.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-2.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
164.06847348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
164.06847348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
98 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
116
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

5 Spectral Information

5.1 1D NMR Spectra

1D NMR Spectra
NMR: 10:91C (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)

5.2 IR Spectra

IR Spectra
IR: 2:108B (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)

7 Chemical Vendors

8 Drug and Medication Information

8.1 Clinical Trials

8.1.1 ClinicalTrials.gov

8.2 Therapeutic Uses

Antimetabolites; Antiviral Agents
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
MEDICATION (VET): TOPICAL TREATMENT OF HERPES GENITALIS IN FEMALE GUINEA PIGS WITH 2-DEOXY-D-GLUCOSE IN EITHER AGAROSE GELS OR MICONAZOLE NITRATE OINTMENT FAILED TO PREVENT DEVELOPMENT OF GENITAL LESIONS OR TO REDUCE THE MEAN TITERS OF RECOVERABLE VIRUS IN VAGINAL SWABS FROM INFECTED ANIMALS.
SHANNON WM ET AL; LACK OF EFFICACY OF 2-DEOXY-D-GLUCOSE IN THE TREATMENT OF EXPERIMENTAL HERPES GENITALIS IN GUINEA PIGS; ANTIMICROB AGENTS CHEMOTHER 21(3) 513 (1982)

9 Pharmacology and Biochemistry

9.1 Absorption, Distribution and Excretion

WHEN THE RENAL EXCRETION OF 2-DEOXYGLUCOSE WAS STUDIED IN DOGS AND RATS BY CONVENTIONAL CLEARANCE AND STOP-FLOW TECHNIQUES, IT WAS REABSORBED BY THE RENAL TUBULES AT AN AVG OF 68-89% OF THE FILTERED LOADS AND THE REABSORPTION SITE WAS IN THE PROXIMAL TUBULES.
WOOSLEY RL ET AL; RENAL TUBULAR TRANSPORT OF 2-DEOXY-D-GLUCOSE IN DOGS AND RATS; J PHARMACOL EXP THER 173(1) 13 (1970)

9.2 Metabolism / Metabolites

2-DEOXY-D-GLUCOSE WAS CONVERTED TO THE 6-PHOSPHATE IN MOUSE TESTIS AND LIVER AFTER IP INJECTION OF 50 MG/KG BODY WT DAILY FOR 7 DAYS.
BURTON LE, WELLS WW; STUDIES ON THE EFFECT OF 5-THIO-D-GLUCOSE AND 2-DEOXY-D-GLUCOSE ON MYO-INOSITOL METABOLISM; ARCH BIOCHEM BIOPHYS 181(2) 384 (1977)

10 Use and Manufacturing

10.1 Uses

2-DEOXYGLUCOSE IS A GLUCOSE ANTIMETABOLITE, INHIBITING GLYCOLYSIS; IT IS A WIDELY USED RESEARCH TOOL TO STUDY GLUCOSE-DEPENDENT OR -MEDIATED REACTIONS
RESEARCH CHEMICAL
SRI
MEDICATION (VET)

10.2 Consumption Patterns

ESSENTIALLY 100% AS A RESEARCH CHEMICAL
SRI

10.3 U.S. Production

(1979) No Data
SRI
(1981) No Data
SRI

10.4 U.S. Imports

(1979) No Data
SRI
(1981) No Data
SRI

10.5 U.S. Exports

(1979) No Data
SRI
(1981) No Data
SRI

10.6 General Manufacturing Information

THE DEOXYSUGARS SUCH AS 2-DEOXYGLUCOSE ARE POTENT HERBICIDES. 2-DEOXYGLUCOSE SPRAYED AT 100 G/ACRE COMPLETELY CONTROLLED PLANTAGO ASIATICA IN AGROPYRON KAMOCHI AND ELEUSINE INDICA.
SUZUKI Y ET AL; HERBICIDAL DEOXY SUGARS; JAPAN KOKAI PATENT NO 77 07423 01/20/77 (MEIJI CONFECTIONARY CO, LTD)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 2
View All
Note
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports. Pictograms displayed are for < 0.1% (0 of 2) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 2 of 2 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 2 of 2 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 2 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Not Classified

11.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
2-Deoxy-D-galactose: Does not have an individual approval but may be used under an appropriate group standard

12 Toxicity

12.1 Toxicological Information

12.1.1 Interactions

2-DEOXYGLUCOSE INJECTED INTRAPERITONEALLY IN RATS IN LARGE DOSES CAUSED CHANGES IN THE ELECTRORETINOGRAM CONSISTING OF A DECR IN BOTH ALPHA- AND BETA-WAVES. THE EFFECT WAS ANTAGONIZED BY D-GLUCOSE.
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 353
SIMULTANEOUS ADMIN OF GLUCOSE @ DOSE EXCEEDING ITS MAX TUBULAR TRANSPORT CAPACITY INHIBITED TUBULAR REABSORPTION OF 2-DEOXYGLUCOSE. THUS, THE PROCESS OF TUBULAR REABSORPTION IS PROBABLY THE SAME AS THAT FOR GLUCOSE.
WOOSLEY RL ET AL; RENAL TUBULAR TRANSPORT OF 2-DEOXY-D-GLUCOSE IN DOGS AND RATS; J PHARMACOL EXP THER 173(1) 13 (1970)
IN ANESTROUS SHEEP, 2-DEOXYGLUCOSE INFUSION INHIBITED LH RELEASE INDUCED BY ESTRADIOL BUT NOT BY LH-RH.
CRUMP AD ET AL; ESTRADIOL-INDUCED LUTEINIZING HORMONE (LH) RELEASE IS INHIBITED BY 2-DEOXYGLUCOSE INFUSION IN SHEEP; J PHYSIOL (LONDON) 330: 93P (1982)
2-DEOXY-D-GLUCOSE INHIBITED REPAIR OF POTENTIALLY LETHAL DAMAGE INDUCED BY X-RAYS IN MOUSE EHRLICH ASCITES TUMOR CELLS.
JAIN VK ET AL; OPTIMIZATION OF CANCER THERAPY: PART I. INHIBITION OF REPAIR OF X-RAY INDUCED POTENTIALLY LETHAL DAMAGE BY 2-DEOXY-D-GLUCOSE IN EHRLICH ASCITES TUMOR CELLS; INDIAN J EXP BIOL 15(9) 711 (1977)
For more Interactions (Complete) data for 2-DEOXY-D-GLUCOSE (6 total), please visit the HSDB record page.

12.1.2 Non-Human Toxicity Excerpts

2-DEOXYGLUCOSE INJECTED INTRAPERITONEALLY IN RATS IN LARGE DOSES CAUSED CHANGES IN THE ELECTRORETINOGRAM CONSISTING OF A DECR IN BOTH ALPHA- AND BETA-WAVES.
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 353
...120 MG/DAY /GIVEN TO RAT/ FROM THE 9TH THROUGH THE 20TH GESTATIONAL DAY... RESORPTIONS WERE 69% AND THE SURVIVING FETUSES WERE ALL MALFORMED. ANOPHTHALMIA, CLEFT LIP AND PALATE AND LESIONS OF THE EXTREMITIES WERE OBSERVED. ...GAVE 1 G/KG ON DAYS 8, 9, 10 OR 11 & FOUND NO MALFORMATIONS IN SURVIVING RAT FETUSES.
Shepard, T. H. Catalog of Teratogenic Agents. 3rd ed. Baltimore, MD.: Johns Hopkins University Press, 1980., p. 99
2-DEOXY-D-GLUCOSE (DGLC) SELECTIVELY INHIBITED VIRUS DNA SYNTHESIS IN HUMAN EMBRYONIC LUNG CELLS INFECTED WITH HUMAN CYTOMEGALOVIRUS (HCMV). THE EFFECTIVE CONCN OF DGLC WAS APPROX 10-FOLD HIGHER IN CULTURE MEDIUM CONTAINING GLUCOSE INSTEAD OF SODIUM PYRUVATE. VIRUS DNA SYNTHESIS COULD BE SELECTIVELY INHIBITED BY ADDN OF DGLC EVEN AFTER INITIATION OF HCMV DNA REPLICATION. APPARENTLY, DGLC INTERFERES WITH THE FUNCTION OF AN EARLY CHROMATIN-ASSOCIATED GLYCOPROTEIN ESSENTIAL FOR VIRUS DNA SYNTHESIS.
RADSAK KD, WEDER D; EFFECT OF 2-DEOXY-D-GLUCOSE ON CYTOMEGALOVIRUS-INDUCED DNA SYNTHESIS IN HUMAN FIBROBLASTS; J GEN VIROL 57(1) 33 (1981)
2-DEOXY-D-GLUCOSE (0.3-1.2 MOL) INJECTED INTO THE 3RD VENTRICLE OF RATS DEPRESSED APPETITE FOR 72 HR. THE BLOOD SUGAR WAS INCR FOR 48 HR, WHILE FREE FATTY ACID INITIALLY INCR BUT DECR BY 24 HR.
TSUTSUI K ET AL; FEEDING SUPPRESSION AND CHANGES OF GLUCOSE, FFA, INSULIN FOLLOWING INTRA-3RD-VENTRICULAR ADMINISTRATION OF DEOXYGLUCOSE; NEUROSCIENCES (KOBE, JPN) 8(1) 116 (1982)
For more Non-Human Toxicity Excerpts (Complete) data for 2-DEOXY-D-GLUCOSE (7 total), please visit the HSDB record page.

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Chemical Co-Occurrences in Literature

13.5 Chemical-Gene Co-Occurrences in Literature

13.6 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 UN GHS Classification

15.5 NORMAN Suspect List Exchange Classification

15.6 EPA DSSTox Classification

15.7 EPA Substance Registry Services Tree

15.8 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Hazardous Substances Data Bank (HSDB)
  7. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  8. ChEBI
  9. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  10. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. Metabolomics Workbench
  13. Springer Nature
  14. Wikidata
    2-deoxy-D-galactose (open form)
    https://www.wikidata.org/wiki/Q27103117
  15. Wikipedia
  16. PubChem
  17. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  18. GHS Classification (UNECE)
  19. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  20. EPA Substance Registry Services
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
CONTENTS