Record Information
Creation date2015-10-09 22:29:16 UTC
Update date2017-01-19 02:36:17 UTC
FoodComEx IDPC000215
FoodDB RecordFDB002257
Chemical Information
DescriptionArginine 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 Number74-79-3
(2S)-2-Amino-5-(carbamimidamido)pentanoic acidbiospider
(2S)-2-Amino-5-(diaminomethylideneamino)pentanoic acidbiospider
(2S)-2-Amino-5-guanidinopentanoic acidbiospider
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acidbiospider
(S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoic acidHMDB
(S)-2-Amino-5-guanidinopentanoic acidbiospider
(S)-2-Amino-5-guanidinovaleric acidbiospider
2-amino-5-Guanidinovaleric acidHMDB
Arginine, INN, USAN; L-formdb_source
FEMA 3819db_source
L-a-Amino-d-guanidinovaleric acidbiospider
L-alpha-Amino-delta-guanidinovaleric acidbiospider
L-Arginine (9CI)biospider
Pentanoic acid, 2-amino-5-((aminoiminomethyl)amino)-, (S)-biospider
S-(+)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acidbiospider
Chemical FormulaC6H14N4O2
IUPAC name(2S)-2-amino-5-carbamimidamidopentanoic acid
InChI IdentifierInChI=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
Isomeric SMILESN[C@@H](CCCNC(N)=N)C(O)=O
Average Molecular Weight174.201
Monoisotopic Molecular Weight174.111675712
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Experimental logP-4.20HANSCH,C ET AL. (1995)
Experimental Water Solubility182 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 244 dec. (anhyd. 105°)DFC
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 2 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci K277
Glentham GM7438
Glentham GM1092
MetaSci HMDB0000517
Sigma-Aldrich HMDB0000517
Toronto Research Chemicals A769505