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Record Information
Version3.6
Creation Date2006-08-13 22:26:44 UTC
Update Date2016-02-11 01:06:45 UTC
HMDB IDHMDB04620
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-a-Acetyl-L-arginine
DescriptionN-alpha-Acetylarginine is one of the guanidino compounds found elevated in the serum of an hemodialyzed renal insufficient (uremic) pediatric population. (PMID 7777105 ). N-alpha-acetylarginine serum levels (and other guanidino compounds) were elevated of all the hyperargininemic patients are higher than the normal range. Untreated hyperargininemic patients have the highest guanidino compound levels in cerebrospinal fluid. (PMID 1690873 ). N-alpha-acetylarginine increases in urine hyperargininemic patients. During a low-arginine diet, together with sodium benzoate therapy, there was a marked decrease in plasma N-alpha-acetylarginine. (PMID 3987036 ).
Structure
Thumb
Synonyms
ValueSource
N-Acetyl-L-arginineMetaCyc
N2-Acetyl-L-arginineMetaCyc
N-alpha-L-Acetyl-arginineMetaCyc
N-a-L-Acetyl-arginineGenerator
N-α-L-acetyl-arginineGenerator
N-alpha-Acetyl-L-arginineHMDB
Chemical FormulaC8H16N4O3
Average Molecular Weight216.2376
Monoisotopic Molecular Weight216.122240398
IUPAC Name(2S)-5-carbamimidamido-2-acetamidopentanoic acid
Traditional NameN~2~-acetyl-L-arginine
CAS Registry Number155-84-0
SMILES
CC(=O)N[C@@H](CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C8H16N4O3/c1-5(13)12-6(7(14)15)3-2-4-11-8(9)10/h6H,2-4H2,1H3,(H,12,13)(H,14,15)(H4,9,10,11)/t6-/m0/s1
InChI KeyInChIKey=SNEIUMQYRCDYCH-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-l-alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Acetamide
  • Secondary carboxylic acid amide
  • Guanidine
  • Carboxamide group
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.77 mg/mLALOGPS
logP-1.7ALOGPS
logP-3.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)12.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.3 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.37 m3·mol-1ChemAxon
Polarizability22.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.25 +/- 0.28 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.15 (0.07-0.23) uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.38 (0.64-2.12) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Not SpecifiedHyperargininemia details
Associated Disorders and Diseases
Disease References
Hyperargininemia
  1. Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [3433275 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023383
KNApSAcK IDNot Available
Chemspider ID60752
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04620
Metagene LinkHMDB04620
METLIN IDNot Available
PubChem Compound67427
PDB IDAAG
ChEBI ID40521
References
Synthesis ReferenceBergmann, Max; Koster, Hans. Rearrangements of peptide-like substances. XII. Arginine and its conversion into ornithino. Z. physiol. Chem. (1926), 159 179-89.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [3433275 ]
  2. Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. [3987036 ]
  3. Marescau B, De Deyn PP, Lowenthal A, Qureshi IA, Antonozzi I, Bachmann C, Cederbaum SD, Cerone R, Chamoles N, Colombo JP, et al.: Guanidino compound analysis as a complementary diagnostic parameter for hyperargininemia: follow-up of guanidino compound levels during therapy. Pediatr Res. 1990 Mar;27(3):297-303. [1690873 ]
  4. De Deyn PP, Robitaille P, Vanasse M, Qureshi IA, Marescau B: Serum guanidino compound levels in uremic pediatric patients treated with hemodialysis or continuous cycle peritoneal dialysis. Correlations between nerve conduction velocities and altered guanidino compound concentrations. Nephron. 1995;69(4):411-7. [7777105 ]