FComEx: D-Arginine (PC000870)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:10 UTC

Update date

2017-01-19 02:36:39 UTC

FoodComEx ID

PC000870

FoodDB Record

FDB023167

Chemical Information

Name

D-Arginine

Description

Arginine 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. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. Arginine can be considered to be a basic amino acid as the part of the side chain nearest to the backbone is long, carbon-containing, and hydrophobic, whereas the end of the side chain is a complex guanidinium group. 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 used to make compounds such as 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. The ratio of L-arginine to lysine is also important: soy and other plant proteins have more L-arginine than animal sources of protein.

CAS Number

157-06-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2R)-2-amino-5-(Carbamimidamido)pentanoate	Generator
(2R)-2-amino-5-(Carbamimidamido)pentanoic acid	ChEBI
(2R)-2-amino-5-Guanidinopentanoate	Generator
(2R)-2-amino-5-Guanidinopentanoic acid	ChEBI
(R)-2-amino-5-Guanidinopentanoate	Generator
(R)-2-amino-5-Guanidinopentanoic acid	ChEBI
D-2-Amino-5-guanidinovalerate	hmdb
D-2-Amino-5-guanidinovaleric acid	hmdb
D-Arginin	ChEBI

Chemical Formula

C6H14N4O2

IUPAC name

(2R)-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-/m1/s1

InChI Key

ODKSFYDXXFIFQN-SCSAIBSYSA-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 d-alpha-amino acids. These are alpha amino acids which have the D-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

D-alpha-amino acids

Alternative Parents