MiMeDB: Showing metabocard for D-Glutamine (MMDBc0000245)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:41:09 UTC

Update Date

2024-10-13 12:01:57 UTC

Metabolite ID

MMDBc0000245

Metabolite Identification

Common Name

D-Glutamine

Description

D-Glutamine is 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(2R)-2,5-Diamino-5-oxopentanoic acid	ChEBI
(2R)-2-Amino-4-carbamoylbutanoic acid	ChEBI
(R)-2,5-Diamino-5-oxopentanoic acid	ChEBI
D-2-Aminoglutaramic acid	ChEBI
D-Glutamin	ChEBI
D-Glutaminsaeure-5-amid	ChEBI
DGN	ChEBI
(2R)-2,5-Diamino-5-oxopentanoate	Generator
(2R)-2-Amino-4-carbamoylbutanoate	Generator
(R)-2,5-Diamino-5-oxopentanoate	Generator
D-2-Aminoglutaramate	Generator
Nutrestore	HMDB
L-Glutamine	HMDB
D Glutamine	HMDB
L Glutamine	HMDB
Glutamine	HMDB

Molecular Formula

C₅H₁₀N₂O₃

Average Mass

146.1445

Monoisotopic Mass

146.069142196

IUPAC Name

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

Traditional Name

D-glutamine

CAS Registry Number

5959-95-5

SMILES

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

InChI Identifier

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

InChI Key

ZDXPYRJPNDTMRX-GSVOUGTGSA-N

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0910000000-c753448f765ddaf37a19	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0920000000-c34d6fc3a22bb5865f8f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-c753448f765ddaf37a19	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-716b1947d48f42862cdf	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9610000000-bfd7aa529a6e7f62de43	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-3900000000-3046f77d887200780992	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-72d0df6d3d9a6e78d3a8	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-470234c1ecc768038678	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-51bf3e28fa7698abc6f9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9500000000-3796f4ab6574acc38758	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-dca2e8c3ca148a6898ac	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-2d7676aa0333d3a585d6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-053r-9000000000-d9b3d51db2e7a344da6b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-51bf3e28fa7698abc6f9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9500000000-3796f4ab6574acc38758	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-2a135ed194fe5a09dd85	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-2d7676aa0333d3a585d6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-053r-9000000000-d9b3d51db2e7a344da6b	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uea-2900000000-643cfc41a048bf920ad2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-9600000000-0714324e1e6a088f13ce	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-39017fe7d7b021cbeeec	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-0f27a44e1f928092e3e4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f95-7900000000-b45c5a70d1db35076e47	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-a8bfd864e03c73b56b35	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-0cb66f41672a11130a67	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056v-5900000000-0f3514e6ed1c9066c5a8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4e42b8ee789c4bca31fc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-a6df7f10f5a6b0c3de4d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-47e7aa43cbaf1b6a9528	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9000000000-98e16d6011265e62f2ab	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Saliva

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
MMDBp0192314	Glutaminase liver isoform, mitochondrial	Enzyme	Q9UI32	Homo sapiens
MMDBp0192319	Glutaminase kidney isoform, mitochondrial	Enzyme	O94925	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

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
Bacteria	Firmicutes	8	Human feces; Human vaginal secretion	Microbial culture
Bacteria	Deinococcus-thermus	2		Microbial culture
Bacteria	Fibrobacteres	1		Microbial culture
Bacteria	Proteobacteria	4	Human ; Human feces	Microbial culture
Bacteria	Fusobacteria	1	Human mucosa; Human supragingival plaque; Human ; Human urine; Human feces; Human saliva; Human subgingival plaque	Microbial culture
Bacteria	Bacteroidetes	1	Human feces	Microbial culture
Eukaryota	Euglenozoa	1		Microbial culture
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected and Quantified	11.3	14.5			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	22.8	44.0			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.

External Links

HMDB ID

HMDB0003423

DrugBank ID

DB02174

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023171

KNApSAcK ID

Not Available

Chemspider ID

128633

KEGG Compound ID

C00819

BioCyc ID

GLUTAMIDE

BiGG ID

Not Available

Wikipedia Link

Glutamine

METLIN ID

6926

PubChem Compound

145815

PDB ID

Not Available

ChEBI ID

17061

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/s0378-4347(00)00310-8. [PubMed:11043757 ]

Showing metabocard for D-Glutamine (MMDBc0000245)

MOL for #<Metabolite:0x00007f46ed35b1b0>

3D MOL for #<Metabolite:0x00007f46ed35b1b0>

3D SDF for #<Metabolite:0x00007f46ed35b1b0>

3D-SDF for #<Metabolite:0x00007f46ed35b1b0>

PDB for #<Metabolite:0x00007f46ed35b1b0>

3D PDB for #<Metabolite:0x00007f46ed35b1b0>

SMILES for #<Metabolite:0x00007f46ed35b1b0>

INCHI for #<Metabolite:0x00007f46ed35b1b0>

Structure for #<Metabolite:0x00007f46ed35b1b0>

3D Structure for #<Metabolite:0x00007f46ed35b1b0>