N2-Succinyl-L-arginine (ECMDB20179) (M2MDB001026)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (118)
Record Information
Version2.0
Creation Date2012-05-31 14:31:41 -0600
Update Date2015-06-03 17:19:28 -0600
Secondary Accession Numbers
  • ECMDB20179
Identification
Name:N2-Succinyl-L-arginine
DescriptionN2-succinyl-l-arginine belongs to the class of Amino Fatty Acids. These are fatty acids contaning an amine group. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • N(2)-(3-Carboxypropanoyl)-L-arginine
  • N(2)-Succinyl-L-arginine
  • N(a)-Succinyl-L-arginine
  • N(alpha)-Succinyl-L-arginine
  • N(α)-Succinyl-L-arginine
  • N-Succinyl-L-arginine
  • N2-succinylarginine
  • N2SucArg
  • N2-succinylarginine
  • NChemBio.2007.11-comp18
  • N~2~-(3-CARBOXYPROPANOYL)-L-ARGININE
  • N~2~-SUCCINYLARGININE
  • SUG
Chemical Formula:C10H18N4O5
Weight:Average: 274.2737
Monoisotopic: 274.127719706
InChI Key:UMOXFSXIFQOWTD-LURJTMIESA-N
InChI:InChI=1S/C10H18N4O5/c11-10(12)13-5-1-2-6(9(18)19)14-7(15)3-4-8(16)17/h6H,1-5H2,(H,14,15)(H,16,17)(H,18,19)(H4,11,12,13)/t6-/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-5-carbamimidamido-2-[(3-carboxy-1-hydroxypropylidene)amino]pentanoic acid
Traditional IUPAC Name:N2-succinyl-L-arginine
SMILES:[H][C@@](CCCNC(N)=N)(N=C(O)CCC(O)=O)C(O)=O
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
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acid
  • Fatty acyl
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Guanidine
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP-1.6ALOGPS
logP-3ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)12.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area169.09 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity74.78 m³·mol⁻¹ChemAxon
Polarizability26.29 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2 Hydrogen ion + 2 Water + N2-Succinyl-L-arginine > Carbon dioxide +2 Ammonium + N2-Succinyl-L-ornithine
L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine
Succinyl-CoA + L-Arginine <> Coenzyme A + N2-Succinyl-L-arginine
N2-Succinyl-L-arginine + 2 Water <> N2-Succinyl-L-ornithine + Carbon dioxide +2 Ammonia
L-Arginine + Succinyl-CoA > Hydrogen ion + N2-Succinyl-L-arginine + Coenzyme A
N2-Succinyl-L-arginine + Water > N2-Succinyl-L-ornithine + Ammonia + Carbon dioxide
Succinyl-CoA + L-Arginine > CoA + N2-Succinyl-L-arginine
N2-Succinyl-L-arginine + 2 Water > N2-Succinyl-L-ornithine +2 Ammonia + Carbon dioxide
L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine
N2-Succinyl-L-arginine + 2 Water <> N2-Succinyl-L-ornithine + Carbon dioxide +2 Ammonia
L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine
N2-Succinyl-L-arginine + 2 Water <> N2-Succinyl-L-ornithine + Carbon dioxide +2 Ammonia
SMPDB Pathways:Not Available
KEGG Pathways:
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:
  • arginine degradation II (AST pathway) AST-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0adi-1490000000-6670c0dc39de04f743a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-024i-3930000000-9b352f228ca7b2d3db27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9500000000-d06b062d16e967b2e764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0c0r-1290000000-e12839ab91579b59e5b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-6690000000-b1305c9747f7ba1fdbf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-af2c42b332b5179d761eView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17705
HMDB IDNot Available
Pubchem Compound ID439968
Kegg IDC03296
ChemSpider ID388993
Wikipedia IDNot Available
BioCyc IDCPD-421
EcoCyc IDCPD-421
Ligand ExpoSUG

Enzymes

Protein Details
1. Arginine N-succinyltransferase
General function:
Involved in arginine N-succinyltransferase activity
Specific function:
Catalyzes the transfer of succinyl-CoA to arginine to produce N(2)-succinylarginine
Gene Name:
astA
Uniprot ID:
P0AE37
Molecular weight:
38456
Reactions
Succinyl-CoA + L-arginine = CoA + N(2)-succinyl-L-arginine.
Protein Details
2. N-succinylarginine dihydrolase
General function:
Involved in N-succinylarginine dihydrolase activity
Specific function:
Catalyzes the hydrolysis of N(2)-succinylarginine into N(2)-succinylornithine, ammonia and CO(2)
Gene Name:
astB
Uniprot ID:
P76216
Molecular weight:
49298
Reactions
N(2)-succinyl-L-arginine + 2 H(2)O = N(2)-succinyl-L-ornithine + 2 NH(3) + CO(2).