Skip to content
Vinony
English
EnglishBahasa IndonesiaDeutschEspañolFrançaisItalianoNederlandsPolskiPortuguêsSvenskaTiếng ViệtTürkçeРусскийالعربيةفارسیहिन्दीไทย한국어中文日本語
L-arginine

File:Arginin_-_Arginine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ173670· pop 67· linked from 2,079 articles

L-arginine

Sign in to save

Also known as L-Arg, (2S)-2-amino-5-guanidinopentanoic acid, (S)-2-amino-5-guanidinopentanoic acid, (2S)-2-amino-5-(carbamimidamido)pentanoic acid, L-(+)-arginine, R, Arg, (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid

thumb|Arginine ball and stick model spinning Arginine is the amino acid with the formula (H2N)(HN)CN(H)(CH2)3CH(NH2)CO2H. The molecule features a guanidino group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (−CO2−) and both the amino and guanidino groups are protonated, resulting in a cation. Only the L-arginine (symbol Arg or R) enantiomer is found naturally. Arg residues are common components of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. The guanidine group in arginine is the precursor for the biosynthesis

OverviewAI-generated

L-arginine is a chemical compound with the formula C₆H₁₄N₄O₂. Its IUPAC name is (2S)-2-amino-5-(diaminomethylideneazaniumyl)pentanoate. The substance has a mass of 174.111676 and a weight of 174.20. It possesses a pKa value of 12.488 and a charge of 0.

The molecule features four hydrogen bond donors and three hydrogen bond acceptors. Its topological polar surface area is 132, and its xlogp is -3.5. L-arginine is associated with the NCI Thesaurus ID C62008. It has been the subject of 151,167 PubMed entries and is referenced by 2,079 other encyclopedia articles.

Synthesized by Vinony from 20 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.

Chemical data

Formula
C6H14N4O2
Molecular weight
174.2 g/mol
IUPAC name
(2S)-2-amino-5-(diaminomethylideneazaniumyl)pentanoate
SMILES
C(C[C@@H](C(=O)[O-])N)C[NH+]=C(N)N
InChIKey
ODKSFYDXXFIFQN-BYPYZUCNSA-N
XLogP
-3.5
Polar surface area
132 Ų
H-bond donors
4
H-bond acceptors
3
Formal charge
0

via PubChem

Research

151,167 papers

via PubMed

Wikidata facts

Has part
carbon
Mass
174.111676
Has use
medication
Show 9 more facts
NCI Thesaurus ID
C62008
found in taxon
soybean
pKa
12.48
Commons category
Arginine
chemical formula
C₆H₁₄N₄O₂
canonical SMILES
C(CC(C(=O)O)N)CN=C(N)N
World Health Organisation international non-proprietary name
arginine
isomeric SMILES
N[C@@H](CCCNC(N)=N)C(O)=O
has characteristic
bitterness
Sources (3)

via Wikidata · CC0

~12 min read

Encyclopedic overview

20 sections
Contents
  • History
  • Sources
  • Production
  • Dietary sources
  • Biosynthesis
  • Function
  • Proteins
  • Precursor
  • Structure
  • Research
  • Growth hormone
  • Herpes simplex virus (cold sores)
  • High blood pressure
  • Schizophrenia
  • Raynaud's phenomenon
  • Safety and potential drug interactions
  • See also
  • References
  • Sources
  • External links

thumb|Arginine ball and stick model spinning Arginine is the amino acid with the formula (H2N)(HN)CN(H)(CH2)3CH(NH2)CO2H. The molecule features a guanidino group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (−CO2−) and both the amino and guanidino groups are protonated, resulting in a cation. Only the L-arginine (symbol Arg or R) enantiomer is found naturally. Arg residues are common components of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. The guanidine group in arginine is the precursor for the biosynthesis of nitric oxide. Like all amino acids, it is a white, water-soluble solid.

The one-letter symbol R was assigned to arginine for its phonetic similarity in English.

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

Gallery (13)

Available in 66 languages

Show 47 more

via Wikidata sitelinks · CC0