N-a-Acetyl-L-arginine (CHEM021810)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:06 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021810
Identification
Common NameN-a-Acetyl-L-arginine
ClassSmall Molecule
DescriptionAn N-acetyl-L-amino acid that is L-arginine in which one of the hydrogens attached to the nitrogen is replaced by an acetyl group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 arginineMeSH, HMDB
N-alpha-AcetylarginineMeSH, HMDB
N(a)-Acetyl-L-arginineGenerator, HMDB
N(Α)-acetyl-L-arginineGenerator, HMDB
N-a-L-Acetyl-arginineGenerator, HMDB
N-Α-L-acetyl-arginineGenerator, HMDB
Chemical FormulaC8H16N4O3
Average Molecular Mass216.238 g/mol
Monoisotopic Mass216.122 g/mol
CAS Registry Number155-84-0
IUPAC Name(2S)-5-carbamimidamido-2-acetamidopentanoic acid
Traditional NameN~2~-acetyl-L-arginine
SMILESCC(=O)N[C@@H](CCCNC(N)=N)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-053u-9800000000-21b92cfd48ed4a2653dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-58b164576b6245ba5e98Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-58a41f9d8b6b341edbadSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01c0-2940000000-8c72ed0fc62303b7f4a2Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ba-0950000000-2fea8c9022bec91ce56bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008a-2910000000-69304c511117e4cfb10cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-368bed42fdebf4188927Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0490000000-399f9d9369bbdc8e156fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0900-1900000000-bd5e452ef23574028f09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9400000000-38ff35c82244b5d8dc7dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01985
HMDB IDHMDB0004620
FooDB IDFDB023383
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID60752
ChEBI ID40521
PubChem Compound ID67427
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11599938
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11672731
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18256486
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2897459
5. Bergmann, Max; Koster, Hans. Rearrangements of peptide-like substances. XII. Arginine and its conversion into ornithino. Z. physiol. Chem. (1926), 159 179-89.
6. 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.
7. 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.
8. 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.
9. 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.