Showing metabocard for N-a-Acetyl-L-arginine (BMDB0004620)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:49 UTC
Update Date2020-04-22 15:13:54 UTC
BMDB IDBMDB0004620
Secondary Accession Numbers
  • BMDB04620
Metabolite Identification
Common NameN-a-Acetyl-L-arginine
DescriptionN-a-Acetyl-L-arginine, also known as N-ac-L-arg-OH, 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, 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. Based on a literature review a significant number of articles have been published on N-a-Acetyl-L-arginine.
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-1ceaef8ce37a7b0824d7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9520000000-c079d35b9012a55883d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-053u-9800000000-21b92cfd48ed4a2653dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-58b164576b6245ba5e98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-58a41f9d8b6b341edbadView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01c0-2940000000-8c72ed0fc62303b7f4a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-1940000000-495d7eb88df38bf7a81fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03mi-2900000000-a1ce241787b062182472View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9400000000-d6685c90df9e6a8f2a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-2930000000-c8a853d3dffa744063acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-4900000000-99f3a540de4819b0d14eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-e57d664a81b0164998d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ba-0950000000-2fea8c9022bec91ce56bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008a-2910000000-69304c511117e4cfb10cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-368bed42fdebf4188927View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0490000000-399f9d9369bbdc8e156fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0900-1900000000-bd5e452ef23574028f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9400000000-38ff35c82244b5d8dc7dView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004620
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
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)Not Available
General ReferencesNot Available