L-glutamine (CHEBI:18050)

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CHEBI:18050 - L-glutamine

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ChEBI Name	L-glutamine

ChEBI ID	CHEBI:18050

ChEBI ASCII Name	L-glutamine

Definition	An optically active form of glutamine having L-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:21308, CHEBI:42899, CHEBI:42812, CHEBI:42814, CHEBI:42943, CHEBI:6227, CHEBI:13110

Supplier Information	ChemicalBook:CB8181541, ChemicalBook:CB5181540, eMolecules:8294178, eMolecules:1012709, ZINC000002508230

Download	Molfile XML SDF

more structures >>

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20 19 0 0 1 0 999 V2000

-2.1880 1.1172 -0.0951 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2620 0.1322 -0.6210 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.1298 -0.1851 0.3902 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8860 -1.2434 -0.1154 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9500 -1.4881 0.8338 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.3663 0.8495 0.0900 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.7992 2.2437 0.1975 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.6898 0.6037 -1.8920 N 0 0 0 0 0 0 0 0 0 0 0 0

2.7222 -0.5334 1.2035 N 0 0 0 0 0 0 0 0 0 0 0 0

2.1324 -2.5992 1.3092 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.7900 -0.8009 -0.8417 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5703 -0.5405 1.3282 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4036 0.7440 0.6184 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3442 -2.1663 -0.3442 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3445 -0.9078 -1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3431 2.8413 0.5448 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4543 0.8162 -2.5346 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1872 1.4736 -1.7016 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3998 -0.6818 1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5974 0.3251 0.8509 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 1 0 0 0 0

7 1 1 0 0 0 0

6 1 2 0 0 0 0

3 2 1 0 0 0 0

2 8 1 0 0 0 0

4 3 1 0 0 0 0

5 4 1 0 0 0 0

9 5 1 0 0 0 0

10 5 2 0 0 0 0

2 11 1 0 0 0 0

3 12 1 0 0 0 0

3 13 1 0 0 0 0

4 14 1 0 0 0 0

4 15 1 0 0 0 0

7 16 1 0 0 0 0

8 17 1 0 0 0 0

8 18 1 0 0 0 0

9 19 1 0 0 0 0

9 20 1 0 0 0 0

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Wikipedia	License
Glutamine (symbol Gln or Q) is an α-amino acid that is used in the biosynthesis of proteins. Its side chain is similar to that of glutamic acid, except the carboxylic acid group is replaced by an amide. It is classified as a charge-neutral, polar amino acid. It is non-essential and conditionally essential in humans, meaning the body can usually synthesize sufficient amounts of it, but in some instances of stress, the body's demand for glutamine increases, and glutamine must be obtained from the diet. It is encoded by the codons CAA and CAG. It is named after glutamic acid, which in turn is named after its discovery in cereal proteins, gluten. In human blood, glutamine is the most abundant free amino acid. The dietary sources of glutamine include especially the protein-rich foods like beef, chicken, fish, dairy products, eggs, vegetables like beans, beets, cabbage, spinach, carrots, parsley, vegetable juices and also in wheat, papaya, Brussels sprouts, celery, kale and fermented foods like miso. The one-letter symbol Q for glutamine was assigned in alphabetical sequence to N for asparagine, being larger by merely one methylene –CH2– group. Note that P was used for proline, and O was avoided due to similarity with D. The mnemonic Qlutamine was also proposed.
Read full article at Wikipedia

Formula

C5H10N2O3

Net Charge

Average Mass

146.14458

Monoisotopic Mass

146.06914

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-/m0/s1

InChIKey

ZDXPYRJPNDTMRX-VKHMYHEASA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). EC 1.14.13.39 (nitric oxide synthase) inhibitor An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). fundamental metabolite Any metabolite produced by all living cells. (via glutamine )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-glutamine (CHEBI:18050) has role Escherichia coli metabolite (CHEBI:76971) L-glutamine (CHEBI:18050) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-glutamine (CHEBI:18050) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) L-glutamine (CHEBI:18050) has role human metabolite (CHEBI:77746) L-glutamine (CHEBI:18050) has role micronutrient (CHEBI:27027) L-glutamine (CHEBI:18050) has role mouse metabolite (CHEBI:75771) L-glutamine (CHEBI:18050) has role nutraceutical (CHEBI:50733) L-glutamine (CHEBI:18050) is a L-α-amino acid (CHEBI:15705) L-glutamine (CHEBI:18050) is a glutamine (CHEBI:28300) L-glutamine (CHEBI:18050) is a glutamine family amino acid (CHEBI:24318) L-glutamine (CHEBI:18050) is a proteinogenic amino acid (CHEBI:83813) L-glutamine (CHEBI:18050) is conjugate acid of L-glutaminate (CHEBI:32665) L-glutamine (CHEBI:18050) is conjugate base of L-glutaminium (CHEBI:32666) L-glutamine (CHEBI:18050) is enantiomer of D-glutamine (CHEBI:17061) L-glutamine (CHEBI:18050) is tautomer of L-glutamine zwitterion (CHEBI:58359)

Incoming	γ-Glu-Gln (CHEBI:73707) has functional parent L-glutamine (CHEBI:18050) γ-glutamyl-β-cyanoalanine (CHEBI:10565) has functional parent L-glutamine (CHEBI:18050) 2-methyl-L-glutamine (CHEBI:43949) has functional parent L-glutamine (CHEBI:18050) L-glutamine derivative (CHEBI:24317) has functional parent L-glutamine (CHEBI:18050) Ala-Asn-Gln-Ser (CHEBI:73331) has functional parent L-glutamine (CHEBI:18050) Ala-Gln-Pro (CHEBI:73347) has functional parent L-glutamine (CHEBI:18050) Ala-Leu-Thr-Gln (CHEBI:73372) has functional parent L-glutamine (CHEBI:18050) Ala-Met-Gln-Gln (CHEBI:137239) has functional parent L-glutamine (CHEBI:18050) Arg-Asn-Gln-Arg (CHEBI:73397) has functional parent L-glutamine (CHEBI:18050) Arg-Asp-Gln-Ser (CHEBI:137242) has functional parent L-glutamine (CHEBI:18050) Asn-Gln (CHEBI:73421) has functional parent L-glutamine (CHEBI:18050) Asn-Met-Gln-Pro (CHEBI:138505) has functional parent L-glutamine (CHEBI:18050) Asp-Gln-Arg (CHEBI:73447) has functional parent L-glutamine (CHEBI:18050) Asp-Gln-Ser (CHEBI:73448) has functional parent L-glutamine (CHEBI:18050) Asp-Leu-Asp-Gln (CHEBI:73428) has functional parent L-glutamine (CHEBI:18050) Asp-Leu-Leu-Gln (CHEBI:73429) has functional parent L-glutamine (CHEBI:18050) Asp-Phe-Asp-Gln (CHEBI:73437) has functional parent L-glutamine (CHEBI:18050) chrysopine (CHEBI:83079) has functional parent L-glutamine (CHEBI:18050) Cys-Gln-Gln (CHEBI:156079) has functional parent L-glutamine (CHEBI:18050) Cys-Met-Gln (CHEBI:144427) has functional parent L-glutamine (CHEBI:18050) Gln-Asn (CHEBI:141428) has functional parent L-glutamine (CHEBI:18050) Gln-Cys-Cys (CHEBI:144458) has functional parent L-glutamine (CHEBI:18050) Gln-Gln (CHEBI:73846) has functional parent L-glutamine (CHEBI:18050) Gln-Leu (CHEBI:141429) has functional parent L-glutamine (CHEBI:18050) Gln-Leu-Leu-Pro (CHEBI:73463) has functional parent L-glutamine (CHEBI:18050) Gln-Phe (CHEBI:141430) has functional parent L-glutamine (CHEBI:18050) Gln-Phe-Trp-Tyr (CHEBI:73464) has functional parent L-glutamine (CHEBI:18050) Gln-Phe-Tyr (CHEBI:156250) has functional parent L-glutamine (CHEBI:18050) Gln-Ser (CHEBI:157840) has functional parent L-glutamine (CHEBI:18050) Gln-Trp (CHEBI:141431) has functional parent L-glutamine (CHEBI:18050) Gln-Tyr (CHEBI:141432) has functional parent L-glutamine (CHEBI:18050) Gln-Val (CHEBI:141433) has functional parent L-glutamine (CHEBI:18050) Glu-Asp-Gln-Gln (CHEBI:73465) has functional parent L-glutamine (CHEBI:18050) Glu-Gln (CHEBI:141435) has functional parent L-glutamine (CHEBI:18050) Glu-Glu-Gln (CHEBI:144559) has functional parent L-glutamine (CHEBI:18050) Glu-Phe-Gln-Gln (CHEBI:73488) has functional parent L-glutamine (CHEBI:18050) indigoidine (CHEBI:79296) has functional parent L-glutamine (CHEBI:18050) Leu-Asp-Gln (CHEBI:73561) has functional parent L-glutamine (CHEBI:18050) Leu-Thr-Gln (CHEBI:73574) has functional parent L-glutamine (CHEBI:18050) Lys-Gln (CHEBI:73600) has functional parent L-glutamine (CHEBI:18050) L-glutaminium (CHEBI:32666) is conjugate acid of L-glutamine (CHEBI:18050) L-glutaminate (CHEBI:32665) is conjugate base of L-glutamine (CHEBI:18050) D-glutamine (CHEBI:17061) is enantiomer of L-glutamine (CHEBI:18050) N²-L-glutamino group (CHEBI:32668) is substituent group from L-glutamine (CHEBI:18050) N⁵-L-glutamino group (CHEBI:32669) is substituent group from L-glutamine (CHEBI:18050) L-glutamine residue (CHEBI:30011) is substituent group from L-glutamine (CHEBI:18050) L-glutaminyl group (CHEBI:32667) is substituent group from L-glutamine (CHEBI:18050) L-glutamine zwitterion (CHEBI:58359) is tautomer of L-glutamine (CHEBI:18050)

IUPAC Name

L-glutamine

Synonyms	Sources
(2S)-2,5-diamino-5-oxopentanoic acid	IUPAC
(2S)-2-amino-4-carbamoylbutanoic acid	JCBN
(S)-2,5-diamino-5-oxopentanoic acid	ChEBI
Glutamic acid 5-amide	HMDB
Glutamic acid amide	HMDB
GLUTAMINE	PDBeChem
L-(+)-glutamine	ChemIDplus
L-2-Aminoglutaramic acid	KEGG COMPOUND
L-2-aminoglutaramic acid	ChEBI
L-2-aminoglutaramic acid	DrugBank
L-glutamic acid γ-amide	NIST Chemistry WebBook
L-Glutamin	ChEBI
L-Glutamine	KEGG COMPOUND
L-Glutaminsäure-5-amid	ChEBI
Levoglutamide	KEGG DRUG
Q	ChEBI

Manual Xrefs	Databases
1311	DrugCentral
C00001359	KNApSAcK
C00064	KEGG COMPOUND
D00015	KEGG DRUG
DB00130	DrugBank
ECMDB00641	ECMDB
GLN	MetaCyc
GLN	PDBeChem
Glutamine	Wikipedia
HMDB0000641	HMDB
LSM-4741	LINCS
YMDB00002	YMDB
View more database links

Registry Numbers	Types	Sources
1723797	Reaxys Registry Number	Reaxys
3509	Gmelin Registry Number	Gmelin
56-85-9	CAS Registry Number	KEGG COMPOUND
56-85-9	CAS Registry Number	NIST Chemistry WebBook
56-85-9	CAS Registry Number	ChemIDplus

Citations

Last Modified

19 April 2021

CHEBI:18050 - L-glutamine

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