Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2015-10-09 22:29:17 UTC
Primary IDFDB002257
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArginine
DescriptionDietary supplement, nutrient Arginine (abbreviated as Arg or R) is an alpha-amino acid. The L-form is one of the 20 most common natural amino acids. (Wikipedia)
CAS Number74-79-3
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-amino-5-(Carbamimidamido)pentanoateGenerator
(2S)-2-Amino-5-(carbamimidamido)pentanoic acidbiospider
(2S)-2-Amino-5-(diaminomethylideneamino)pentanoic acidbiospider
(2S)-2-amino-5-GuanidinopentanoateGenerator
(2S)-2-Amino-5-guanidinopentanoic acidbiospider
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoatebiospider
(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acidbiospider
(S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoateHMDB
(S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoic acidHMDB
(S)-2-amino-5-GuanidinopentanoateGenerator
(S)-2-Amino-5-guanidinopentanoic acidbiospider
(S)-2-amino-5-GuanidinovalerateGenerator
(S)-2-Amino-5-guanidinovaleric acidbiospider
2-amino-5-GuanidinovalerateHMDB
2-amino-5-Guanidinovaleric acidHMDB
5-[(Aminoiminomethyl)amino]-L-Norvalinebiospider
Argbiospider
Arginine, INN, USAN; L-formdb_source
FEMA 3819db_source
L-(+)-Argininebiospider
L-a-Amino-d-guanidinovaleratebiospider
L-a-Amino-d-guanidinovaleric acidbiospider
L-alpha-Amino-delta-guanidinovaleratebiospider
L-alpha-Amino-delta-guanidinovaleric acidbiospider
L-ArgChEBI
L-ArgininChEBI
L-ArginineChEBI
L-Arginine (9CI)biospider
N5-(Aminoiminomethyl)-L-ornithinebiospider
Pentanoic acid, 2-amino-5-((aminoiminomethyl)amino)-, (S)-biospider
RChEBI
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
Bioavailability1ChemAxon
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 KeyInChIKey=ODKSFYDXXFIFQN-BYPYZUCNSA-N
Isomeric SMILESN[C@@H](CCCNC(N)=N)C(O)=O
Average Molecular Weight174
Monoisotopic Molecular Weight174
Classification
DescriptionThis compound 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
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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0a4i-1910000000-0191c1a63652c493660bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9810000000-eb6eb73302b678cf0a24View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-9700000000-e47b41cff0e873f53932View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1920000000-8ae5af11398835d26bedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-1910000000-0191c1a63652c493660bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9810000000-eb6eb73302b678cf0a24View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-9700000000-e47b41cff0e873f53932View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1920000000-8ae5af11398835d26bedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0900000000-afc3ca93f8fbf54ec9f4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9100000000-60db59de76b9a9b5bfc8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-8900000000-f47c4f9480612fdbc962View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-3900000000-8c82418f7b35a97fb9b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-19b62da79866318c52ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-64b046d21bdcbb8d5923View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-e07b937b6867d1f62293View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-87ab853583aab2973cfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-28814246b728a51e761cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-cfe7e406be2172e94fbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0910000000-478a8345915bc15d85b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-c930c47ecbe6975a00fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-fa6be0f9ce4ee4c30738View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-3425ee9829935182c0d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fk9-0946231100-3d57d2304dcb33feab3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-5b6dd6fb263ea09289fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-dfe35b3438d19320d8cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-f666ab7e5354bce67a2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03kd-0977452210-046c4b70bd0ec351c41dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-2f51e43e530976d63633View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-b9ebb7ebccee1a313888View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-5379b6fb6ea2313101f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-004i-0900000000-02b2bc83599dc6944f2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00fr-7900000000-b7cd48e0aca6a6256968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00fr-7900000000-b7cd48e0aca6a6256968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00fr-7900000000-4e69a6ce7b97433937eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-835751d54af24bd337e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-2d2b5fd7617ccb227bb1View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).