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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:55 UTC

HMDB ID

HMDB0000517

Secondary Accession Numbers

HMDB00517

Metabolite Identification

Common Name

L-Arginine

Description

Arginine (Arg), also known as L-argninine, 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. Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-asparagine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Arginine is found in all organisms ranging from bacteria to plants to animals. Arginine is an essential amino acid that is physiologically active in the L-form. It is classified as a charged, basic, aliphatic amino acid. Arginine is considered to be a basic amino acid as it has a strongly basic 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. 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. 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. Arginine also plays an important role in cell division, immunity and wound healing. Arginine is the immediate precursor of nitric oxide (NO), an important signaling molecule which can act as a second messenger, as well as an intercellular messenger which regulates vasodilation, and also has functions in the immune system's reaction to infection. Nitric oxide is made via the enzyme nitric oxide synthase (PMID 10690324 ). Arginine is also a precursor for several important nitrogen-containing compounds including urea, ornithine, and agmatine. Arginine is necessary for the synthesis of creatine and can be used for the synthesis of polyamines (mainly through ornithine and to a lesser degree through agmatine, citrulline, and glutamate.) The presence of asymmetric dimethylarginine (ADMA) in serum or plasma, a close relative of arginine, inhibits the nitric oxide synthase reaction. ADMA is considered a marker for vascular disease, just as L-arginine is considered a sign of a healthy endothelium. In large doses, L-arginine also stimulates the release of several hormones including human 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 ). 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. This can lead to general anabolism or a more anabolic state (PMID: 21311355 ). In line with these findings, arginine supplementation has been shown to increase muscle mass in several animal studies (PMID: 18683021 ) and to significantly improve aerobic capacity and VO2 max in male athletes (PMID: 28120856 ). 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. The ratio of arginine to kynurenine (A/K) has recently been found to be a good indicator of the degree of septicemia or catabolic stress, with an A/K ratio of between 0.3 to 15 being indicative severe disease (high risk of death), and an A/K ratio of between 15-22 being more typical of someone with moderate inflammation and an A/K ratio of between 22-50 being typical of healthy individuals (PMID: 33134953 ). 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0       3.779   1.797   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.779   0.257   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.113  -0.513   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.445  -0.513   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.445  -2.054   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.111   0.257   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.222  -0.513   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.556   0.257   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.890  -0.513   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.224   0.257   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -4.224   1.797   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -5.558  -0.513   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    9    7                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Amino-5-(carbamimidamido)pentanoic acid	ChEBI
(2S)-2-Amino-5-guanidinopentanoic acid	ChEBI
(S)-2-Amino-5-guanidinopentanoic acid	ChEBI
(S)-2-Amino-5-guanidinovaleric acid	ChEBI
Arg	ChEBI
Arginine	ChEBI
L-(+)-Arginine	ChEBI
L-Arg	ChEBI
L-Arginin	ChEBI
R	ChEBI
(2S)-2-Amino-5-(carbamimidamido)pentanoate	Generator
(2S)-2-Amino-5-guanidinopentanoate	Generator
(S)-2-Amino-5-guanidinopentanoate	Generator
(S)-2-Amino-5-guanidinovalerate	Generator
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoate	HMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acid	HMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoate	HMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid	HMDB
2-Amino-5-guanidinovalerate	HMDB
2-Amino-5-guanidinovaleric acid	HMDB
5-[(Aminoiminomethyl)amino]-L-norvaline	HMDB
L-a-Amino-D-guanidinovalerate	HMDB
L-a-Amino-D-guanidinovaleric acid	HMDB
L-alpha-Amino-delta-guanidinovalerate	HMDB
L-alpha-Amino-delta-guanidinovaleric acid	HMDB
N5-(Aminoiminomethyl)-L-ornithine	HMDB
DL-Arginine acetate, monohydrate	HMDB
L-Isomer arginine	HMDB
Monohydrate DL-arginine acetate	HMDB
L Arginine	HMDB
Arginine, L isomer	HMDB
Arginine, L-isomer	HMDB
Hydrochloride, arginine	HMDB
Arginine hydrochloride	HMDB
DL Arginine acetate, monohydrate	HMDB

Chemical Formula

C₆H₁₄N₄O₂

Average Molecular Weight

174.201

Monoisotopic Molecular Weight

174.111675712

IUPAC Name

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

Traditional Name

L-arginine

CAS Registry Number

74-79-3

SMILES

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

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

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.

Showing metabocard for L-Arginine (HMDB0000517)

MOL for HMDB0000517 (L-Arginine)

3D MOL for HMDB0000517 (L-Arginine)

3D SDF for HMDB0000517 (L-Arginine)

3D-SDF for HMDB0000517 (L-Arginine)

PDB for HMDB0000517 (L-Arginine)

3D PDB for HMDB0000517 (L-Arginine)

SMILES for HMDB0000517 (L-Arginine)

INCHI for HMDB0000517 (L-Arginine)

Structure for HMDB0000517 (L-Arginine)

3D Structure for HMDB0000517 (L-Arginine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized