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D-glutamine

PubChem CID
145815
Structure
D-glutamine_small.png
D-glutamine_3D_Structure.png
Molecular Formula
Synonyms
  • D-glutamine
  • 5959-95-5
  • H-D-Gln-OH
  • D-2-Aminoglutaramic acid
  • (R)-2,5-diamino-5-oxopentanoic acid
Molecular Weight
146.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
D-glutamine is the D-enantiomer of glutamine. It has a role as a mouse metabolite. It is a D-alpha-amino acid and a glutamine. It is a conjugate base of a D-glutaminium. It is a conjugate acid of a D-glutaminate. It is an enantiomer of a L-glutamine. It is a tautomer of a D-glutamine zwitterion.
A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells.
D-Glutamine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
See also: Glutamine (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
D-glutamine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-D-Gln-OH
Sequence
Q
PLN
H-{d}Q-OH
HELM
PEPTIDE1{[dQ]}$$$$
IUPAC
D-glutamine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2R)-2,5-diamino-5-oxopentanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

ZDXPYRJPNDTMRX-GSVOUGTGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

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

3.2 Molecular Formula

C5H10N2O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 European Community (EC) Number

3.3.3 UNII

3.3.4 ChEBI ID

3.3.5 ChEMBL ID

3.3.6 DrugBank ID

3.3.7 DSSTox Substance ID

3.3.8 HMDB ID

3.3.9 KEGG ID

3.3.10 Metabolomics Workbench ID

3.3.11 Nikkaji Number

3.3.12 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • D Glutamine
  • D-Glutamine
  • Glutamine
  • L Glutamine
  • L-Glutamine

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
146.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-3.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
146.06914219 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
146.06914219 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
106 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
146
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
1
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)

4.2 Experimental Properties

4.2.1 Physical Description

Solid

5 Spectral Information

5.1 1D NMR Spectra

1D NMR Spectra

5.1.1 1H NMR Spectra

1 of 3
View All
Spectra ID
Frequency
600 MHz
Solvent
H2O
Shifts [ppm]
2.13, 2.44, 3.76
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2 of 3
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Spectra ID
Frequency
600 MHz
Solvent
H2O
Shifts [ppm]
3.76, 2.13, 2.44
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5.1.2 13C NMR Spectra

Instrument Name
Bruker WP-80
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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5.2 2D NMR Spectra

5.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
3.76:56.78:0.99, 2.44:33.52:0.81, 2.13:28.89:1.00
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5.3 Mass Spectrometry

5.3.1 GC-MS

1 of 6
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

156.15 100

155.15 31.27

245.15 21.68

147.1 15.87

157.15 14.51

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Notes
instrument=GCMS-2010 Plus, Shimadzu
2 of 6
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Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

156.0 100

155.0 35.14

147.0 22.52

157.0 16.42

128.0 12.01

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies

5.3.2 MS-MS

1 of 8
View All
Spectra ID
Instrument Type
LC-ESI-QQ
Ionization Mode
positive
Top 5 Peaks

130.1 100

84.2 1.82

147.3 1.75

83.0 1.44

148.2 0.24

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Notes
instrument=API3000, Applied Biosystems
2 of 8
View All
Spectra ID
Instrument Type
LC-ESI-QQ
Ionization Mode
positive
Top 5 Peaks

84.2 100

130.0 64

102.0 1.14

83.4 0.34

147.1 0.18

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Notes
instrument=API3000, Applied Biosystems

5.3.3 LC-MS

1 of 8
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
10 V
Precursor m/z
147
Precursor Adduct
[M+H]+
Top 5 Peaks

130.1 999

84.2 18

147.3 18

83 14

148.2 2

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License
CC BY-NC-SA
2 of 8
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
20 V
Precursor m/z
147
Precursor Adduct
[M+H]+
Top 5 Peaks

84.2 999

130 639

102 11

83.4 3

147.1 2

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License
CC BY-NC-SA

5.3.4 Other MS

1 of 3
View All
Authors
Miyagawa H, Akimoto S, Yamasaki K, GL Sciences Inc.
Instrument
GCMS-2010 Plus, Shimadzu
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Column Name
InertCap 5MS/NP 0.25 mmI.D. x 30 m, df=0.25 um
Retention Time
723.18
Top 5 Peaks

156.15 999

155.15 312

245.15 217

147.1 159

157.15 145

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License
CC BY-SA
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
147.0764186
Ionization Mode
positive
Retention Time
0.3781451037917958
Top 5 Peaks

115.05128846132571 0.31

128.0575664613257 0.14

131.0465704613257 0.11

127.0493374613257 0.08

129.0623014613257 0.04

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7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

Cytoplasm

9 Use and Manufacturing

9.1 Uses

Use (kg; approx.) in Germany (2009): >1000

Consumption (g per capita; approx.) in Germany (2009): 0.0122

Calculated removal (%): 92.1

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

STOT SE 3 (100%)

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Wiley References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Protein Bound 3D Structures

13.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

13.2 Chemical-Target Interactions

13.3 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 KEGG: Metabolite

16.4 ChemIDplus

16.5 UN GHS Classification

16.6 EPA DSSTox Classification

16.7 LOTUS Tree

16.8 MolGenie Organic Chemistry Ontology

17 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. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. 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
  7. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  8. ChEBI
  9. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  10. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  11. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  12. Natural Product Activity and Species Source (NPASS)
    (2R)-5-Amino-2-Azaniumyl-5-Oxopentanoate
    https://bidd.group/NPASS/compound.php?compoundID=NPC190184
  13. MassBank Europe
  14. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  15. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  16. Japan Chemical Substance Dictionary (Nikkaji)
  17. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  18. Metabolomics Workbench
  19. NMRShiftDB
  20. 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/
    GLUTAMINE
  21. Protein Data Bank in Europe (PDBe)
  22. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  23. SpectraBase
  24. Springer Nature
  25. Wikidata
  26. Wiley
  27. 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
  28. PubChem
  29. GHS Classification (UNECE)
  30. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  31. PATENTSCOPE (WIPO)
  32. NCBI
CONTENTS