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L-glutamine

File:L-Glutamin_-_L-Glutamine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ181619· pop 63· linked from 962 articles

L-glutamine

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Also known as Gln, Q, L-2-aminoglutaramic acid, (S)-2,5-diamino-5-oxopentanoic acid, Glutamic acid 5-amide, L-(+)-glutamine, Levoglutamide, (2S)-2,5-Diamino-5-oxopentanoic acid

thumb|Glutamine ball and stick model spinning 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 n

OverviewAI-generated

L-glutamine is a chemical compound with the formula C₅H₁₀N₂O₃. Its IUPAC name is (2S)-2,5-diamino-5-oxopentanoic acid. The substance has a mass of 146.069 and a weight of 146.14. It possesses a charge of 0, an xlogp of -3.1, and a topological polar surface area of 106. The molecule contains three hydrogen bond donors and four hydrogen bond acceptors.

The compound is identified by the NCI Thesaurus ID C522 and the PubChem CID 5961. Its canonical SMILES notation is C(CC(=O)N)C(C(=O)O)N, while its isomeric SMILES is N[C@@H](CCC(N)=O)C(O)=O. The InChIKey for L-glutamine is ZDXPYRJPNDTMRX-VKHMYHEASA-N.

L-glutamine is associated with a Commons category titled "Glutamine." A search for the term yields 58,302 entries in PubMed. Additionally, the subject is referenced by 962 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.drug_name
L-glutamine oral powder
Drug.tradename
Endari, Nutrestore
Drug.MedlinePlus
a617035
Drug.DailyMedID
Glutamine
Drug.routes_of_administration
By mouth
Drug.class
Gastrointestinal agent
Drug.ATC_prefix
A16
Drug.ATC_suffix
AA03
Drug.legal_US
Rx-only
Drug.CAS_number
56-85-9
Drug.PubChem
5961
Drug.DrugBank
DB00130
Drug.ChemSpiderID
5746
Drug.UNII
0RH81L854J
Drug.KEGG
D00015
Drug.KEGG2
C00064
Drug.ChEBI
58359
Drug.ChEMBL
930

via Wikipedia infobox

Chemical data

Formula
C5H10N2O3
Molecular weight
146.14 g/mol
IUPAC name
(2S)-2,5-diamino-5-oxopentanoic acid
SMILES
C(CC(=O)N)[C@@H](C(=O)O)N
InChIKey
ZDXPYRJPNDTMRX-VKHMYHEASA-N
XLogP
-3.1
Polar surface area
106 Ų
H-bond donors
3
H-bond acceptors
4
Formal charge
0

via PubChem

Research

58,302 papers

via PubMed

~9 min read

Encyclopedic overview

15 sections
Contents
  • Functions
  • Roles in metabolism
  • Production
  • Biosynthesis
  • Uses
  • Nutrition
  • Sickle cell disease
  • Medical food
  • Safety
  • Structure
  • Research
  • Scientific application
  • See also
  • References
  • External links

thumb|Glutamine ball and stick model spinning 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.

Excerpted from Wikipedia’s “L-glutamine” article, available under the CC BY-SA 4.0 licence.

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