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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 22:26:44 UTC
Update Date2020-02-26 21:25:09 UTC
HMDB IDHMDB0004620
Secondary Accession Numbers
  • HMDB04620
Metabolite Identification
Common NameN-a-Acetyl-L-arginine
DescriptionN-a-Acetyl-L-arginine, also known as N-ac-L-arg-OH or N-alpha-acetylarginine, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-a-Acetyl-L-arginine serum levels (and other guanidino compounds) were elevated of all the hyperargininemic patients are higher than the normal range. N-a-Acetyl-L-arginine is a very strong basic compound (based on its pKa). Untreated hyperargininemic patients have the highest guanidino compound levels in cerebrospinal fluid. N-a-Acetyl-L-arginine is one of the guanidino compounds found elevated in the serum of an hemodialyzed renal insufficient (uremic) pediatric population. Outside of the human body, N-a-Acetyl-L-arginine has been detected, but not quantified in, apples and loquats. This could make N-a-acetyl-L-arginine a potential biomarker for the consumption of these foods. N-a-Acetyl-L-arginine, with regard to humans, has been found to be associated with several diseases such as uremia and colorectal cancer; N-a-acetyl-L-arginine has also been linked to the inborn metabolic disorder hyperargininemia. During a low-arginine diet, together with sodium benzoate therapy, there was a marked decrease in plasma N-alpha-acetylarginine. N-a-Acetyl-L-arginine increases in urine hyperargininemic patients.
Structure
Data?1582752309
Synonyms
ValueSource
N-Ac-L-arg-OHChEBI
N-Acetyl-L-arginineChEBI
N(2)-Acetyl-L-arginineChEBI
N-alpha-Acetyl-L-arginineHMDB
N-alpha-L-Acetyl-arginineHMDB
N2-Acetyl-L-arginineHMDB
Acetyl arginineHMDB
N-alpha-AcetylarginineHMDB
N(a)-Acetyl-L-arginineHMDB
N(Α)-acetyl-L-arginineHMDB
N-a-L-Acetyl-arginineGenerator
N-Α-L-acetyl-arginineGenerator
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 KeySNEIUMQYRCDYCH-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated 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 ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Guanidine
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

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 g/LALOGPS
logP-1.7ALOGPS
logP-3.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)12.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.37 m³·mol⁻¹ChemAxon
Polarizability22.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-1ceaef8ce37a7b0824d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9520000000-c079d35b9012a55883d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-1940000000-495d7eb88df38bf7a81fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03mi-2900000000-a1ce241787b062182472Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9400000000-d6685c90df9e6a8f2a03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-2930000000-c8a853d3dffa744063acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-4900000000-99f3a540de4819b0d14eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-e57d664a81b0164998d5Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.25 +/- 0.28 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0838 +/- 0.115 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.15 (0.07-0.23) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.38 (0.64-2.12) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.520 +/- 0.660 uMAdult (>18 years old)Both
Uremia
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Not SpecifiedHyperargininemia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
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. [PubMed:3433275 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01985
Phenol Explorer Compound IDNot Available
FooDB IDFDB023383
KNApSAcK IDNot Available
Chemspider ID60752
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67427
PDB IDNot Available
ChEBI ID40521
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed:3433275 ]
  2. 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. [PubMed:7777105 ]
  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. [PubMed:1690873 ]
  4. 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. [PubMed:3987036 ]