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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
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Formula C5H10N2O3
Net Charge 0
Average Mass 146.14458
Monoisotopic Mass 146.069
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:10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:3055) See: PubMed
Saccharomyces cerevisiae (NCBI:4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Chemical Role(s): 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

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).
(via L-alpha-amino acid )
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)
Arg-Asn-Gln-Arg (CHEBI:73397) has functional parent L-glutamine (CHEBI:18050)
Asn-Gln (CHEBI:73421) 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)
Gln-Gln (CHEBI:73846) has functional parent L-glutamine (CHEBI:18050)
Gln-Leu-Leu-Pro (CHEBI:73463) has functional parent L-glutamine (CHEBI:18050)
Gln-Phe-Trp-Tyr (CHEBI:73464) has functional parent L-glutamine (CHEBI:18050)
Glu-Asp-Gln-Gln (CHEBI:73465) 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
Database Links Databases
C00001359 KNApSAcK
C00064 KEGG COMPOUND
D00015 KEGG DRUG
DB00130 DrugBank
ECMDB00641 ECMDB
GLN MetaCyc
GLN PDBeChem
Glutamine Wikipedia
HMDB00641 HMDB
LSM-4741 LINCS
YMDB00002 YMDB
View more database links
Registry Numbers Types Sources
1723797 Reaxys Registry Number Reaxys
1723797 Beilstein Registry Number ChemIDplus
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 Waiting for Citations Types Sources
11139387 PubMed citation Europe PMC
15204730 PubMed citation Europe PMC
22055478 PubMed citation Europe PMC
22206385 PubMed citation Europe PMC
22451274 PubMed citation Europe PMC
22453904 PubMed citation Europe PMC
22575040 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
Last Modified
23 March 2016