Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2020-09-17 15:38:36 UTC
Primary IDFDB002257
Secondary Accession Numbers
  • FDB030954
Chemical Information
FooDB NameArginine
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
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-5-(carbamimidamido)pentanoic acidChEBI
(2S)-2-Amino-5-guanidinopentanoic acidChEBI
(S)-2-Amino-5-guanidinopentanoic acidChEBI
(S)-2-Amino-5-guanidinovaleric acidChEBI
ArgChEBI
ArginineChEBI
L-(+)-ArginineChEBI
L-ArgChEBI
L-ArgininChEBI
RChEBI
(2S)-2-Amino-5-(carbamimidamido)pentanoateGenerator
(2S)-2-Amino-5-guanidinopentanoateGenerator
(S)-2-Amino-5-guanidinopentanoateGenerator
(S)-2-Amino-5-guanidinovalerateGenerator
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoateHMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acidHMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoateHMDB
(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acidHMDB
2-Amino-5-guanidinovalerateHMDB
2-Amino-5-guanidinovaleric acidHMDB
5-[(Aminoiminomethyl)amino]-L-norvalineHMDB
L-a-Amino-D-guanidinovalerateHMDB
L-a-Amino-D-guanidinovaleric acidHMDB
L-alpha-Amino-delta-guanidinovalerateHMDB
L-alpha-Amino-delta-guanidinovaleric acidHMDB
N5-(Aminoiminomethyl)-L-ornithineHMDB
DL-Arginine acetate, monohydrateHMDB
L-Isomer arginineHMDB
Monohydrate DL-arginine acetateHMDB
L ArginineHMDB
Arginine, L isomerHMDB
Arginine, L-isomerHMDB
Hydrochloride, arginineHMDB
Arginine hydrochlorideHMDB
DL Arginine acetate, monohydrateHMDB
(2S)-2-amino-5-(Carbamimidamido)pentanoateGenerator
(2S)-2-Amino-5-(diaminomethylideneamino)pentanoic acidbiospider
(2S)-2-amino-5-GuanidinopentanoateGenerator
(S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoateHMDB
(S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoic acidHMDB
(S)-2-amino-5-GuanidinopentanoateGenerator
(S)-2-amino-5-GuanidinovalerateGenerator
2-amino-5-GuanidinovalerateHMDB
2-amino-5-Guanidinovaleric acidHMDB
5-[(Aminoiminomethyl)amino]-L-Norvalinebiospider
Arginine, INN, USAN; L-formdb_source
FEMA 3819db_source
L-a-Amino-d-guanidinovaleratebiospider
L-a-Amino-d-guanidinovaleric acidbiospider
L-ArginineChEBI
L-Arginine (9CI)biospider
Pentanoic acid, 2-amino-5-((aminoiminomethyl)amino)-, (S)-biospider
S-(+)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acidbiospider
S-Argininemanual
Predicted Properties
PropertyValueSource
Water Solubility2.28 g/LALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)12.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.92 m³·mol⁻¹ChemAxon
Polarizability17.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
InChI KeyODKSFYDXXFIFQN-BYPYZUCNSA-N
Isomeric SMILESN[C@@H](CCCNC(N)=N)C(O)=O
Average Molecular Weight174.201
Monoisotopic Molecular Weight174.111675712
Classification
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
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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.37%; H 8.10%; N 32.16%; O 18.37%DFC
Melting PointMp 244 dec. (anhyd. 105°)DFC
Boiling PointNot Available
Experimental Water Solubility182 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-4.20HANSCH,C ET AL. (1995)
Experimental pKapKa3 12.48 (guanido)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +48.1 (c, 1 in 5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0a4i-1910000000-0191c1a63652c493660bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9810000000-eb6eb73302b678cf0a24JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-9700000000-e47b41cff0e873f53932JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1920000000-8ae5af11398835d26bedJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-1910000000-0191c1a63652c493660bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9810000000-eb6eb73302b678cf0a24JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-9700000000-e47b41cff0e873f53932JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1920000000-8ae5af11398835d26bedJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0900000000-afc3ca93f8fbf54ec9f4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9100000000-60db59de76b9a9b5bfc8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-8900000000-f47c4f9480612fdbc962JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fk9-0946231100-3d57d2304dcb33feab3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-5b6dd6fb263ea09289fcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-dfe35b3438d19320d8cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-f666ab7e5354bce67a2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03kd-0977452210-046c4b70bd0ec351c41dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-2f51e43e530976d63633JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-b9ebb7ebccee1a313888JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-5379b6fb6ea2313101f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-835751d54af24bd337e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-2d2b5fd7617ccb227bb1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-dfe35b3438d19320d8cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-f666ab7e5354bce67a2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-b9ebb7ebccee1a313888JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-5379b6fb6ea2313101f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-835751d54af24bd337e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-2d2b5fd7617ccb227bb1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-3900000000-8c82418f7b35a97fb9b3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-19b62da79866318c52ddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-64b046d21bdcbb8d5923JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-e07b937b6867d1f62293JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-87ab853583aab2973cfbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-28814246b728a51e761cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-cfe7e406be2172e94fbaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0910000000-478a8345915bc15d85b5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-c930c47ecbe6975a00fcJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID6082
ChEMBL IDCHEMBL1485
KEGG Compound IDC00062
Pubchem Compound ID6322
Pubchem Substance IDNot Available
ChEBI ID16467
Phenol-Explorer IDNot Available
DrugBank IDDB00125
HMDB IDHMDB00517
CRC / DFC (Dictionary of Food Compounds) IDCHQ98-B:CHQ90-T
EAFUS ID248
Dr. Duke IDL-ARGININE|ARGININE
BIGG ID33707
KNApSAcK IDC00001340
HET ID1FOL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1068131
SuperScent IDNot Available
Wikipedia IDArginine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti encephalopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatitic62868 Any compound that is able to prevent damage to the liver.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti impotence52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti infertility52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
aphrodisiacDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hypoammonemicDUKE
nitric-oxide-genicDUKE
pituitary stimulantDUKE
spermigenicDUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
Glycine amidinotransferase, mitochondrialGATMP50440
Arginine--tRNA ligase, cytoplasmicRARSP54136
Argininosuccinate synthaseASS1P00966
Argininosuccinate lyaseASLP04424
Arginine decarboxylaseADCQ96A70
High affinity cationic amino acid transporter 1SLC7A1P30825
Probable arginine--tRNA ligase, mitochondrialRARS2Q5T160
NOS1 mutantNOS1B3VK56
[Protein ADP-ribosylarginine] hydrolaseADPRHP54922
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Glycine and Serine MetabolismSMP00004 map00260
Transcription/TranslationSMP00019 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).