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Record Information
Version1.0
Creation date2011-09-21 00:29:05 UTC
Update date2019-11-26 03:21:09 UTC
Primary IDFDB023383
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-alpha-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) [HMDB]. N-alpha-Acetyl-L-arginine is found in loquat and apple.
CAS Number155-84-0
Structure
Thumb
Synonyms
SynonymSource
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-arginineHMDB
N-Α-L-acetyl-arginineHMDB
N-a-Acetyl-L-argininehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
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 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
Chemical FormulaC8H16N4O3
IUPAC name(2S)-5-carbamimidamido-2-acetamidopentanoic acid
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
Isomeric SMILESCC(=O)N[C@@H](CCCNC(N)=N)C(O)=O
Average Molecular Weight216.2376
Monoisotopic Molecular Weight216.122240398
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-alpha-Acetyl-L-arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9300000000-1ceaef8ce37a7b0824d7Spectrum
Predicted GC-MSN-alpha-Acetyl-L-arginine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9520000000-c079d35b9012a55883d2Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-1940000000-495d7eb88df38bf7a81fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03mi-2900000000-a1ce241787b062182472Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9400000000-d6685c90df9e6a8f2a03Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-2930000000-c8a853d3dffa744063acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-4900000000-99f3a540de4819b0d14eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-e57d664a81b0164998d5Spectrum
NMRNot Available
ChemSpider ID60752
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID67427
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01985
HMDB IDHMDB04620
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDN-ALPHA-ACETYL-L-ARGININE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDAAG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).