ECMDB: D-Glutamine (ECMDB03423) (M2MDB000500)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (3)XML

Proteins (197)

Record Information

Version

2.0

Creation Date

2012-05-31 13:59:03 -0600

Update Date

2015-09-13 12:56:13 -0600

Secondary Accession Numbers

ECMDB03423

Identification

Name:

D-Glutamine

Description

D-glutamine is a non-essential amino acid and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen and is an important energy source for many cells.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

D-2-Aminoglutaramate
D-2-Aminoglutaramic acid
Glutamide
Nutrestore

Chemical Formula:

C₅H₁₀N₂O₃

Weight:

Average: 146.1445
Monoisotopic: 146.069142196

InChI Key:

ZDXPYRJPNDTMRX-GSVOUGTGSA-N

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

CAS number:

5959-95-5

IUPAC Name:

(2R)-2-amino-4-carbamoylbutanoic acid

Traditional IUPAC Name:

D-glutamine

SMILES:

N[C@H](CCC(N)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-alpha-amino acids

Alternative Parents

Substituents

D-alpha-amino acid
Fatty acid
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:17061 )
glutamine (CHEBI:17061 )
Other amino acids (C00819 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	97.8 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-4	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	33.11 m³·mol⁻¹	ChemAxon
Polarizability	13.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

D-Glutamine + Water <> D-Glutamic acid + Ammonia
D-Glutamine + Water > D-Glutamic acid + Ammonia
D-Glutamine + Water <> D-Glutamic acid + Ammonia

SMPDB Pathways:

D-Glutamine and D-glutamate metabolism

PW000769

KEGG Pathways:

D-Glutamine and D-glutamate metabolism ec00471

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0910000000-c753448f765ddaf37a19	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0920000000-c34d6fc3a22bb5865f8f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-c753448f765ddaf37a19	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-716b1947d48f42862cdf	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9610000000-bfd7aa529a6e7f62de43	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-3900000000-3046f77d887200780992	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-72d0df6d3d9a6e78d3a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-470234c1ecc768038678	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-51bf3e28fa7698abc6f9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9500000000-3796f4ab6574acc38758	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-dca2e8c3ca148a6898ac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-2d7676aa0333d3a585d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-053r-9000000000-d9b3d51db2e7a344da6b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-51bf3e28fa7698abc6f9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9500000000-3796f4ab6574acc38758	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-2a135ed194fe5a09dd85	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-2d7676aa0333d3a585d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-053r-9000000000-d9b3d51db2e7a344da6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uea-2900000000-643cfc41a048bf920ad2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-9600000000-0714324e1e6a088f13ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-39017fe7d7b021cbeeec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-0f27a44e1f928092e3e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f95-7900000000-b45c5a70d1db35076e47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-a8bfd864e03c73b56b35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-0cb66f41672a11130a67	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056v-5900000000-0f3514e6ed1c9066c5a8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4e42b8ee789c4bca31fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-a6df7f10f5a6b0c3de4d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-47e7aa43cbaf1b6a9528	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9000000000-98e16d6011265e62f2ab	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Thorsen G, Bergquist J: Chiral separation of amino acids in biological fluids by micellar electrokinetic chromatography with laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl. 2000 Aug 18;745(2):389-97. Pubmed: 11043757
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Qian, Shao-Song; Wu, Xiao-Yan; Li, Jia-You; Liu, Yi; Chen, Ran; Jiao, Qing-Cai. Preparation of D-glutamine from glutamic acid. Youji Huaxue (2006), 26(4), 514-517.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	17061
HMDB ID	HMDB03423
Pubchem Compound ID	145815
Kegg ID	C00819
ChemSpider ID	128633
Wikipedia ID	Glutamine
BioCyc ID	GLUTAMIDE
EcoCyc ID	GLUTAMIDE
Ligand Expo	DGN

Enzymes

Protein Details

1. Glutaminase 2

General function:: Involved in glutaminase activity
Specific function:: L-glutamine + H(2)O = L-glutamate + NH(3)
Gene Name:: glsA2
Uniprot ID:: P0A6W0
Molecular weight:: 33515

Reactions

L-glutamine + H(2)O = L-glutamate + NH(3).

Protein Details

2. Glutaminase 1

General function:: Involved in glutaminase activity
Specific function:: L-glutamine + H(2)O = L-glutamate + NH(3)
Gene Name:: glsA1
Uniprot ID:: P77454
Molecular weight:: 32903

Reactions

L-glutamine + H(2)O = L-glutamate + NH(3).

Protein Details

3. Glutamine transport system permease protein glnP

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for glutamine; probably responsible for the translocation of the substrate across the membrane
Gene Name:: glnP
Uniprot ID:: P0AEQ6
Molecular weight:: 24364

Transporters

Protein Details

1. Uncharacterized amino-acid ABC transporter ATP-binding protein yecC

General function:: Involved in nucleotide binding
Specific function:: Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:: yecC
Uniprot ID:: P37774
Molecular weight:: 27677

Protein Details

2. Inner membrane amino-acid ABC transporter permease protein yecS

General function:: Involved in transporter activity
Specific function:: Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:: yecS
Uniprot ID:: P0AFT2
Molecular weight:: 24801

Protein Details

3. Glutamine transport system permease protein glnP

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for glutamine; probably responsible for the translocation of the substrate across the membrane
Gene Name:: glnP
Uniprot ID:: P0AEQ6
Molecular weight:: 24364

D-Glutamine (ECMDB03423) (M2MDB000500)

Structure for #<Compound:0xae4b27d4>

Enzymes

Reactions

Reactions

Transporters