FComEx: Arginine (PC000215)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:16 UTC

Update date

2017-01-19 02:36:17 UTC

FoodComEx ID

PC000215

FoodDB Record

FDB002257

Chemical Information

Name

Arginine

Description

Arginine or l-arginine, abbreviated Arg or R, is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Pre-term infants are unable to effectively synthesize arginine, making it nutritionally essential for them. Adults, however, synthesize arginine from glutamate via citrulline. Arginine is a basic amino acid as its side chain contains a positively charged guanidinium group, which is highly polar, at the end of a hydrophobic aliphatic hydrocarbon chain. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is a precursor of nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of the hormones, growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. While many studies suggested that plant based protein-rich foods like soy protein, which contain less arginine, reduced cardiovascular risk compared to arginine rich foods like animal proteins, other studies have found little or null effects (PMID: 20042191).

CAS Number

74-79-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S)-2-amino-5-(Carbamimidamido)pentanoate	Generator
(2S)-2-Amino-5-(carbamimidamido)pentanoic acid	biospider
(2S)-2-Amino-5-(diaminomethylideneamino)pentanoic acid	biospider
(2S)-2-amino-5-Guanidinopentanoate	Generator
(2S)-2-Amino-5-guanidinopentanoic acid	biospider
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoate	biospider
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acid	biospider
(S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoate	HMDB
(S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoic acid	HMDB
(S)-2-amino-5-Guanidinopentanoate	Generator
(S)-2-Amino-5-guanidinopentanoic acid	biospider
(S)-2-amino-5-Guanidinovalerate	Generator
(S)-2-Amino-5-guanidinovaleric acid	biospider
2-amino-5-Guanidinovalerate	HMDB
2-amino-5-Guanidinovaleric acid	HMDB
5-[(Aminoiminomethyl)amino]-L-Norvaline	biospider
Arg	biospider
Arginine, INN, USAN; L-form	db_source
FEMA 3819	db_source
L-(+)-Arginine	biospider
L-a-Amino-d-guanidinovalerate	biospider
L-a-Amino-d-guanidinovaleric acid	biospider
L-alpha-Amino-delta-guanidinovalerate	biospider
L-alpha-Amino-delta-guanidinovaleric acid	biospider
L-Arg	ChEBI
L-Arginin	ChEBI
L-Arginine	ChEBI
L-Arginine (9CI)	biospider
N5-(Aminoiminomethyl)-L-ornithine	biospider
Pentanoic acid, 2-amino-5-((aminoiminomethyl)amino)-, (S)-	biospider
R	ChEBI
S-(+)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid	biospider
S-Arginine	manual

Chemical Formula

C6H14N4O2

IUPAC name

(2S)-2-amino-5-carbamimidamidopentanoic acid

InChI Identifier

InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1

InChI Key

ODKSFYDXXFIFQN-BYPYZUCNSA-N

Isomeric SMILES

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

Average Molecular Weight

174.201

Monoisotopic Molecular Weight

174.111675712

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-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

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Fatty acid
Guanidine
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16467 )
L-alpha-amino acid (CHEBI:16467 )
arginine (CHEBI:16467 )
glutamine family amino acid (CHEBI:16467 )
Common amino acids (C00062 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-4.20	HANSCH,C ET AL. (1995)
Experimental Water Solubility	182 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 244 dec. (anhyd. 105°)	DFC

Foods of Origin