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Showing metabocard for Guanidinosuccinic acid (HMDB0003157)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:37 UTC
Update Date2023-02-21 17:16:33 UTC
HMDB IDHMDB0003157
Secondary Accession Numbers
  • HMDB03157
Metabolite Identification
Common NameGuanidinosuccinic acid
DescriptionGuanidinosuccinic acid (GSA) has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ). It is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003157 (Guanidinosuccinic acid)

  Mrv1652305271900142D          

 12 11  0  0  1  0            999 V2000
   17.8448   -7.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2726   -7.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4160   -8.5524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9870   -8.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -6.4900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4160   -7.7274    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9870   -7.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -7.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7015   -7.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -8.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -9.7898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8448   -8.5524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  6  3  1  1  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
  3 10  1  0  0  0  0
M  END
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3D MOL for HMDB0003157 (Guanidinosuccinic acid)

HMDB0003157
     RDKit          3D
Guanidinosuccinic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
    2.3517    1.2236   -0.7266 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9894    0.3547    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -0.5085    0.7556 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750    0.2282    0.3663 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386   -0.4411   -0.4429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7849   -0.3211   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -0.7392    1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062   -1.8063    1.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0783    0.0527    2.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756    0.1653   -1.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   -0.4379   -2.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107    1.5114   -1.8347 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543    1.5711   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7460   -0.6971    1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6982   -0.9586    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    0.7390    1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0840   -1.5348   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2947   -0.9004   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    0.7235   -0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730   -0.2035    3.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3161    1.9790   -1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  6
  6 18  1  0
  6 19  1  0
  9 20  1  0
 12 21  1  0
M  END
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3D SDF for HMDB0003157 (Guanidinosuccinic acid)

  Mrv1652305271900142D          

 12 11  0  0  1  0            999 V2000
   17.8448   -7.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2726   -7.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4160   -8.5524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9870   -8.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -6.4900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4160   -7.7274    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9870   -7.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -7.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7015   -7.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -8.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1303   -9.7898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8448   -8.5524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  6  3  1  1  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
  3 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003157

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=N)N[C@@H](CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1

> <INCHI_KEY>
VVHOUVWJCQOYGG-REOHCLBHSA-N

> <FORMULA>
C5H9N3O4

> <MOLECULAR_WEIGHT>
175.1427

> <EXACT_MASS>
175.059305791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.134534487236891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-carbamimidamidobutanedioic acid

> <ALOGPS_LOGP>
-1.55

> <JCHEM_LOGP>
-3.274604686023357

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.946751033807223

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.981814631239839

> <JCHEM_PKA_STRONGEST_BASIC>
12.226333162290631

> <JCHEM_POLAR_SURFACE_AREA>
136.5

> <JCHEM_REFRACTIVITY>
47.247299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-amidino-L-aspartic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0003157 (Guanidinosuccinic acid)

HMDB0003157
     RDKit          3D
Guanidinosuccinic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
    2.3517    1.2236   -0.7266 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9894    0.3547    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -0.5085    0.7556 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750    0.2282    0.3663 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3386   -0.4411   -0.4429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7849   -0.3211   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -0.7392    1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062   -1.8063    1.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0783    0.0527    2.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756    0.1653   -1.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   -0.4379   -2.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107    1.5114   -1.8347 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543    1.5711   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7460   -0.6971    1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6982   -0.9586    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    0.7390    1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0840   -1.5348   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2947   -0.9004   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585    0.7235   -0.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730   -0.2035    3.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3161    1.9790   -1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  6
  6 18  1  0
  6 19  1  0
  9 20  1  0
 12 21  1  0
M  END
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PDB for HMDB0003157 (Guanidinosuccinic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      33.310 -14.424   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.642 -13.654   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      30.643 -15.964   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0      27.976 -15.964   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      31.977 -12.115   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      30.643 -14.424   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.976 -14.424   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.977 -13.654   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.309 -13.654   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.977 -16.734   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      31.977 -18.274   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      33.310 -15.964   0.000  0.00  0.00           N+0
CONECT    1    8                                                            
CONECT    2    7                                                            
CONECT    3    6   10                                                       
CONECT    4    7                                                            
CONECT    5    8                                                            
CONECT    6    3    8    9                                                  
CONECT    7    2    4    9                                                  
CONECT    8    1    5    6                                                  
CONECT    9    6    7                                                       
CONECT   10   11   12    3                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0003157 (Guanidinosuccinic acid)

COMPND    HMDB0003157
HETATM    1  N1  UNL     1       2.352   1.224  -0.727  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.989   0.355   0.080  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.887  -0.508   0.756  1.00  0.00           N  
HETATM    4  N3  UNL     1       0.575   0.228   0.366  1.00  0.00           N  
HETATM    5  C2  UNL     1      -0.339  -0.441  -0.443  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.785  -0.321  -0.158  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.291  -0.739   1.136  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.906  -1.806   1.284  1.00  0.00           O  
HETATM    9  O2  UNL     1      -2.078   0.053   2.236  1.00  0.00           O  
HETATM   10  C5  UNL     1      -0.176   0.165  -1.838  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.193  -0.438  -2.785  1.00  0.00           O  
HETATM   12  O4  UNL     1      -0.511   1.511  -1.835  1.00  0.00           O  
HETATM   13  H1  UNL     1       3.154   1.571  -1.132  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.746  -0.697   1.765  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.698  -0.959   0.294  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.318   0.739   1.277  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.084  -1.535  -0.531  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.295  -0.900  -1.008  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.158   0.724  -0.349  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.973  -0.204   3.184  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.316   1.979  -1.574  1.00  0.00           H  
CONECT    1    2    2   13
CONECT    2    3    4
CONECT    3   14   15
CONECT    4    5   16
CONECT    5    6   10   17
CONECT    6    7   18   19
CONECT    7    8    8    9
CONECT    9   20
CONECT   10   11   11   12
CONECT   12   21
END
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SMILES for HMDB0003157 (Guanidinosuccinic acid)

NC(=N)N[C@@H](CC(O)=O)C(O)=O
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INCHI for HMDB0003157 (Guanidinosuccinic acid)

InChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(2S)-2-Carbamimidamidobutanedioic acidChEBI
L-N-Amidinoaspartic acidChEBI
N-(Aminoiminomethyl)-L-aspartic acidChEBI
N-Amidino-L-aspartic acidKegg
(2S)-2-CarbamimidamidobutanedioateGenerator
L-N-AmidinoaspartateGenerator
N-(Aminoiminomethyl)-L-aspartateGenerator
N-Amidino-L-aspartateGenerator
GuanidinosuccinateGenerator
N-Carbamimidoyl-L-aspartic acidHMDB
Guanidinosuccinic acid, (DL)-isomerMeSH, HMDB
Guanidinosuccinic acidChEBI
Chemical FormulaC5H9N3O4
Average Molecular Weight175.1427
Monoisotopic Molecular Weight175.059305791
IUPAC Name(2S)-2-carbamimidamidobutanedioic acid
Traditional NameN-amidino-L-aspartic acid
CAS Registry Number6133-30-8
SMILES
NC(=N)N[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1
InChI KeyVVHOUVWJCQOYGG-REOHCLBHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.068Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available130.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002066
[M+H]+Not Available137.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00002066
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.106 uMAdult (>18 years old)BothCirrhosis details
BloodDetected and Quantified20.1 +/- 1.6 uMAdult (>18 years old)BothChronic renal failure details
BloodDetected and Quantified8.17 +/- 1.71 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified37.143 +/- 19.429 uMAdult (>18 years old)Both
Uremia		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8. [PubMed:7752905 ]
Chronic renal failure
  1. Kikuchi T, Orita Y, Ando A, Mikami H, Fujii M, Okada A, Abe H: Liquid-chromatographic determination of guanidino compounds in plasma and erythrocyte of normal persons and uremic patients. Clin Chem. 1981 Nov;27(11):1899-902. [PubMed:7296840 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023116
KNApSAcK IDNot Available
Chemspider ID388951
KEGG Compound IDC03139
BioCyc IDCPD-599
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID10
PubChem Compound439918
PDB IDNot Available
ChEBI ID17072
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00013446
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cohen BD: Methyl group deficiency and guanidino production in uremia. Mol Cell Biochem. 2003 Feb;244(1-2):31-6. [PubMed:12701806 ]
  2. 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 ]
  3. Torremans A, Marescau B, Van Dam D, Van Ginneken C, Van Meir F, Van Bogaert PP, D'Hooge R, de Vente J, De Deyn PP: GSA: behavioral, histological, electrophysiological and neurochemical effects. Physiol Behav. 2005 Feb 15;84(2):251-64. Epub 2005 Jan 8. [PubMed:15708777 ]
  4. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]