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Showing NP-Card for Guanidinosuccinic acid (NP0000426)

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Record Information
Version2.0
Created at2006-05-22 15:12:37 UTC
Updated at2021-06-29 00:47:41 UTC
NP-MRD IDNP0000426
Secondary Accession NumbersNone
Natural Product 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 NP0000426 (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
Download

3D MOL for NP0000426 (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
Download

3D SDF for NP0000426 (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>
NP0000426

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000426 (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
Download

PDB for NP0000426 (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 NP0000426 (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 NP0000426 (Guanidinosuccinic acid)

NC(=N)N[C@@H](CC(O)=O)C(O)=O
Download

INCHI for NP0000426 (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 JSmol
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)-isomerHMDB
Guanidinosuccinic acidChEBI
Chemical FormulaC5H9N3O4
Average Mass175.1427 Da
Monoisotopic Mass175.05931 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Eriobotrya japonicaLOTUS Database
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.068Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.82 g/LALOGPS
logP-1.6ALOGPS
logP-3.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)12.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability15.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003157
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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. Yamamoto H, Suzuki M, Matsuta R, Sasaki K, Kang MI, Kami K, Tatara Y, Itoh K, Nakaji S: Capillary Electrophoresis Mass Spectrometry-Based Metabolomics of Plasma Samples from Healthy Subjects in a Cross-Sectional Japanese Population Study. Metabolites. 2021 May 13;11(5). pii: metabo11050314. doi: 10.3390/metabo11050314. [PubMed:34068294 ]
  5. Yang X, Wang J, Wang H, Li X, He C, Liu L: Metabolomics study of fibroblasts damaged by UVB and BaP. Sci Rep. 2021 May 27;11(1):11176. doi: 10.1038/s41598-021-90186-7. [PubMed:34045475 ]
  6. Taniguchi E, Tashiro A, Hattori A, Furuse M, Yasuo S: Photoperiodic changes in hippocampal neurogenesis and plasma metabolomic profiles in relation to depression-like behavior in mice. Behav Brain Res. 2021 Apr 9;403:113136. doi: 10.1016/j.bbr.2021.113136. Epub 2021 Jan 20. [PubMed:33482168 ]