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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2017-11-01 19:34:05 UTC

Update Date

2023-02-21 17:33:46 UTC

HMDB ID

HMDB0240212

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dimethylguanidino valeric acid

Description

Dimethylguanidino valeric acid or DMGV is a product formed from the transamination of asymmetric dimethylarginine (ADMA) via the enzyme alanine-glyoxylate aminotransferase 2 (AGXT2). This pathway is involved in nitric oxide regulation. DMGV has been detected in both blood and urine (PMID: 21945966 ). More recently DMGV has been identified as an independent plasma biomarker of nonalcoholic fatty liver disease (NAFLD). Furthermore, plasma DMGV levels are correlated with biopsy-proven nonalcoholic steatohepatitis (NASH). Plasma DMGV levels have also been found to decline in parallel with improvements in post-procedure cardiometabolic parameters. Plasma DMGV levels have been shown to be able to predict the development of type 2 diabetes up to 12 years before disease onset (PMID: 29083323 ). Baseline plasma levels of DMGV have been shown to be positively associated with body fat percentage, abdominal visceral fat, very low-density lipoprotein cholesterol (VLDL), and triglycerides. Plasma levels of DMGV are inversely associated with insulin sensitivity, low-density lipoprotein cholesterol, high-density lipoprotein size, and high-density lipoprotein cholesterol (HDL). Overall, DMGV is associated with partial resistance to metabolic health benefits of regular exercise (PMID: 31166569 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0240212
     RDKit          3D
Dimethylguanidino valeric acid
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.8043    0.7454   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543   -0.2150    0.2157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584   -1.5672    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5217    0.2064    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672    1.3748    1.0162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3915   -0.5918    0.2719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -0.7280   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144    0.4862   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    0.9681   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1901   -0.0429   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.1714   -0.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817    0.3300    0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3437    1.4366    1.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998   -0.5853    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8429    0.5209    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5892    1.7782    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8224    0.7509   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794   -2.3152   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177   -1.7306    0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -1.7997    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    1.7146    1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0173   -1.1309    1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8984   -1.6555   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407   -0.8836   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    1.3035   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    0.2837   -2.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    1.3741    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161    1.8074   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9945   -0.6640   -0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 14 29  1  0
M  END


  Mrv1652311101718012D          

 14 13  0  0  0  0            999 V2000
   -2.0535    0.8705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0535    1.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7680    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.3669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246    0.8705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8043    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5187    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9477    0.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9477   -0.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    0.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332    1.6955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
 10 14  2  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240212

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C(=N)NCCCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N3O3/c1-11(2)8(9)10-5-3-4-6(12)7(13)14/h3-5H2,1-2H3,(H2,9,10)(H,13,14)

> <INCHI_KEY>
GLWRPXRMUUZNMD-UHFFFAOYSA-N

> <FORMULA>
C8H15N3O3

> <MOLECULAR_WEIGHT>
201.226

> <EXACT_MASS>
201.111341355

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.5661927301935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(N',N'-dimethylcarbamimidamido)-2-oxopentanoic acid

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-1.771705349382374

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.33223164644344

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1006296048574677

> <JCHEM_PKA_STRONGEST_BASIC>
12.776711299702953

> <JCHEM_POLAR_SURFACE_AREA>
93.49000000000001

> <JCHEM_REFRACTIVITY>
61.58770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(N',N'-dimethylcarbamimidamido)-2-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240212
     RDKit          3D
Dimethylguanidino valeric acid
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.8043    0.7454   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543   -0.2150    0.2157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584   -1.5672    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5217    0.2064    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672    1.3748    1.0162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3915   -0.5918    0.2719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -0.7280   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144    0.4862   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    0.9681   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1901   -0.0429   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.1714   -0.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817    0.3300    0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3437    1.4366    1.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998   -0.5853    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8429    0.5209    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5892    1.7782    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8224    0.7509   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794   -2.3152   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177   -1.7306    0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -1.7997    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    1.7146    1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0173   -1.1309    1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8984   -1.6555   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407   -0.8836   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    1.3035   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    0.2837   -2.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    1.3741    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161    1.8074   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9945   -0.6640   -0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 14 29  1  0
M  END

HEADER    PROTEIN                                 10-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-NOV-17         0                                  
HETATM    1  N   UNK     0      -3.833   1.625   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.500   0.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.833   3.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.167   0.855   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.500  -0.685   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      -1.166   1.625   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.168   0.855   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.501   1.625   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.835   0.855   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.169   1.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.502   0.855   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.502  -0.685   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.836   1.625   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.169   3.165   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2    7                                                       
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0240212
HETATM    1  C1  UNL     1      -3.804   0.745  -0.318  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.854  -0.215   0.216  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.258  -1.567   0.445  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.522   0.206   0.509  1.00  0.00           C  
HETATM    5  N2  UNL     1      -1.367   1.375   1.016  1.00  0.00           N  
HETATM    6  N3  UNL     1      -0.391  -0.592   0.272  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.283  -0.728  -0.991  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.014   0.486  -1.457  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.104   0.968  -0.567  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.190  -0.043  -0.353  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.173  -1.171  -0.902  1.00  0.00           O  
HETATM   12  C8  UNL     1       4.282   0.330   0.523  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.344   1.437   1.090  1.00  0.00           O  
HETATM   14  O3  UNL     1       5.300  -0.585   0.737  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.843   0.521   0.002  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.589   1.778   0.065  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.822   0.751  -1.425  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.679  -2.315  -0.167  1.00  0.00           H  
HETATM   19  H5  UNL     1      -4.318  -1.731   0.167  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.191  -1.800   1.536  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.416   1.715   1.243  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.017  -1.131   1.098  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.898  -1.656  -0.981  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.541  -0.884  -1.757  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.257   1.303  -1.514  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.390   0.284  -2.473  1.00  0.00           H  
HETATM   27  H13 UNL     1       1.769   1.374   0.383  1.00  0.00           H  
HETATM   28  H14 UNL     1       2.616   1.807  -1.126  1.00  0.00           H  
HETATM   29  H15 UNL     1       5.995  -0.664  -0.007  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4
CONECT    3   18   19   20
CONECT    4    5    5    6
CONECT    5   21
CONECT    6    7   22
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   11   12
CONECT   12   13   13   14
CONECT   14   29
END

HMDB0240212
     RDKit          3D
Dimethylguanidino valeric acid
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.8043    0.7454   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543   -0.2150    0.2157 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2584   -1.5672    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5217    0.2064    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672    1.3748    1.0162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3915   -0.5918    0.2719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826   -0.7280   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144    0.4862   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038    0.9681   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1901   -0.0429   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1727   -1.1714   -0.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817    0.3300    0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3437    1.4366    1.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998   -0.5853    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8429    0.5209    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5892    1.7782    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8224    0.7509   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794   -2.3152   -0.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3177   -1.7306    0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -1.7997    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    1.7146    1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0173   -1.1309    1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8984   -1.6555   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5407   -0.8836   -1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    1.3035   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    0.2837   -2.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    1.3741    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161    1.8074   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9945   -0.6640   -0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 14 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dimethylguanidino valerate	Generator
DMGV	HMDB
5-[[(Dimethylamino)iminomethyl]amino]-2-oxopentanoic acid	HMDB
Α-keto-δ-(NG,ng-dimethylguanidino)valeric acid	HMDB
Αlpha-keto-delta-(NG,ng-dimethylguanidino)valeric acid	HMDB
2-oxo-5-(3,3-Dimethylguanidine-1-yl)pentanoate	HMDB
(a-Keto-dimethyl-delta-N,N-dimethylguanidynol) valerate	HMDB
(a-Keto-dimethyl-delta-N,N-dimethylguanidynol) valeric acid	HMDB
(alpha-Keto-dimethyl-delta-N,N-dimethylguanidynol) valerate	HMDB
(Α-keto-dimethyl-δ-N,N-dimethylguanidynol) valerate	HMDB
(Α-keto-dimethyl-δ-N,N-dimethylguanidynol) valeric acid	HMDB
Dimethylguanidinovaleric acid	HMDB
Dimethylguanidinovalerate	HMDB
2-oxo-5-(3,3-Dimethylguanidine-1-yl)pentanoic acid	HMDB
5-[[(Dimethylamino)iminomethyl]amino]-2-oxopentanoate	HMDB
Α-keto-δ-(NG,ng-dimethylguanidino)valerate	HMDB
alpha-keto-delta-(NG,ng-dimethylguanidino)valeric acid	HMDB
(alpha-Keto-dimethyl-delta-N,N-dimethylguanidynol)valerate	HMDB
(alpha-Keto-dimethyl-delta-N,N-dimethylguanidynol)valeric acid	HMDB

Chemical Formula

C₈H₁₅N₃O₃

Average Molecular Weight

201.226

Monoisotopic Molecular Weight

201.111341355

IUPAC Name

5-(N',N'-dimethylcarbamimidamido)-2-oxopentanoic acid

Traditional Name

5-(N',N'-dimethylcarbamimidamido)-2-oxopentanoic acid

CAS Registry Number

107347-90-0

SMILES

CN(C)C(=N)NCCCC(=O)C(O)=O

InChI Identifier

InChI=1S/C8H15N3O3/c1-11(2)8(9)10-5-3-4-6(12)7(13)14/h3-5H2,1-2H3,(H2,9,10)(H,13,14)

InChI Key

GLWRPXRMUUZNMD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Guanidine
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21945966)

Excreta

Biofluid or Excreta

Urine (PMID: 21945966)

Source

Exogenous

Exogenous (HMDB: HMDB0240212)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.7	ALOGPS
logP	-1.8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	12.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.59 m³·mol⁻¹	ChemAxon
Polarizability	20.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	145.498	31661259
AllCCS	[M+H]+	145.686	31661259
DeepCCS	[M+H]+	143.839	30932474
DeepCCS	[M-H]-	140.011	30932474
DeepCCS	[M-2H]-	177.448	30932474
DeepCCS	[M+Na]+	153.09	30932474
AllCCS	[M+H]+	145.7	32859911
AllCCS	[M+H-H2O]+	142.1	32859911
AllCCS	[M+NH4]+	149.0	32859911
AllCCS	[M+Na]+	150.0	32859911
AllCCS	[M-H]-	145.5	32859911
AllCCS	[M+Na-2H]-	146.7	32859911
AllCCS	[M+HCOO]-	148.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	0.84 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8217 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	420.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	64.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	276.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	254.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	816.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	583.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	684.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	873.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	502.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	197.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dimethylguanidino valeric acid	CN(C)C(=N)NCCCC(=O)C(O)=O	2963.4	Standard polar	33892256
Dimethylguanidino valeric acid	CN(C)C(=N)NCCCC(=O)C(O)=O	1926.3	Standard non polar	33892256
Dimethylguanidino valeric acid	CN(C)C(=N)NCCCC(=O)C(O)=O	1951.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dimethylguanidino valeric acid,1TMS,isomer #1	CN(C)C(=N)NCCCC(=O)C(=O)O[Si](C)(C)C	1991.2	Semi standard non polar	33892256
Dimethylguanidino valeric acid,1TMS,isomer #2	CN(C)C(=N)NCCC=C(O[Si](C)(C)C)C(=O)O	2128.0	Semi standard non polar	33892256
Dimethylguanidino valeric acid,1TMS,isomer #3	CN(C)C(=N[Si](C)(C)C)NCCCC(=O)C(=O)O	2036.9	Semi standard non polar	33892256
Dimethylguanidino valeric acid,1TMS,isomer #4	CN(C)C(=N)N(CCCC(=O)C(=O)O)[Si](C)(C)C	2045.2	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #1	CN(C)C(=N)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2092.9	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #1	CN(C)C(=N)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1819.8	Standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #1	CN(C)C(=N)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3048.7	Standard polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #2	CN(C)C(=N[Si](C)(C)C)NCCCC(=O)C(=O)O[Si](C)(C)C	1962.2	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #2	CN(C)C(=N[Si](C)(C)C)NCCCC(=O)C(=O)O[Si](C)(C)C	1708.3	Standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #2	CN(C)C(=N[Si](C)(C)C)NCCCC(=O)C(=O)O[Si](C)(C)C	2885.4	Standard polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #3	CN(C)C(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1990.0	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #3	CN(C)C(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1862.2	Standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #3	CN(C)C(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2828.0	Standard polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #4	CN(C)C(=N[Si](C)(C)C)NCCC=C(O[Si](C)(C)C)C(=O)O	2106.0	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #4	CN(C)C(=N[Si](C)(C)C)NCCC=C(O[Si](C)(C)C)C(=O)O	1806.4	Standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #4	CN(C)C(=N[Si](C)(C)C)NCCC=C(O[Si](C)(C)C)C(=O)O	3028.0	Standard polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #5	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2094.5	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #5	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1960.6	Standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #5	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3040.4	Standard polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #6	CN(C)C(=N[Si](C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C	2060.5	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #6	CN(C)C(=N[Si](C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C	1861.9	Standard non polar	33892256
Dimethylguanidino valeric acid,2TMS,isomer #6	CN(C)C(=N[Si](C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C	2809.1	Standard polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #1	CN(C)C(=N[Si](C)(C)C)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2054.7	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #1	CN(C)C(=N[Si](C)(C)C)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1748.6	Standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #1	CN(C)C(=N[Si](C)(C)C)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2693.3	Standard polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #2	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2060.3	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #2	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1980.1	Standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #2	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2621.7	Standard polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #3	CN(C)C(=N[Si](C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2028.0	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #3	CN(C)C(=N[Si](C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1847.8	Standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #3	CN(C)C(=N[Si](C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2402.0	Standard polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #4	CN(C)C(=N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2113.3	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #4	CN(C)C(=N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1959.3	Standard non polar	33892256
Dimethylguanidino valeric acid,3TMS,isomer #4	CN(C)C(=N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2604.4	Standard polar	33892256
Dimethylguanidino valeric acid,4TMS,isomer #1	CN(C)C(=N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2075.8	Semi standard non polar	33892256
Dimethylguanidino valeric acid,4TMS,isomer #1	CN(C)C(=N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1866.9	Standard non polar	33892256
Dimethylguanidino valeric acid,4TMS,isomer #1	CN(C)C(=N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2297.3	Standard polar	33892256
Dimethylguanidino valeric acid,1TBDMS,isomer #1	CN(C)C(=N)NCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2233.3	Semi standard non polar	33892256
Dimethylguanidino valeric acid,1TBDMS,isomer #2	CN(C)C(=N)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2338.0	Semi standard non polar	33892256
Dimethylguanidino valeric acid,1TBDMS,isomer #3	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCCC(=O)C(=O)O	2282.3	Semi standard non polar	33892256
Dimethylguanidino valeric acid,1TBDMS,isomer #4	CN(C)C(=N)N(CCCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2297.5	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #1	CN(C)C(=N)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2524.1	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #1	CN(C)C(=N)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2197.9	Standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #1	CN(C)C(=N)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3027.9	Standard polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #2	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2408.6	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #2	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2094.0	Standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #2	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	2873.4	Standard polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #3	CN(C)C(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2454.4	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #3	CN(C)C(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2277.6	Standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #3	CN(C)C(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2880.2	Standard polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #4	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2522.9	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #4	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2131.8	Standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #4	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2998.1	Standard polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #5	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2552.3	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #5	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2340.4	Standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #5	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3019.4	Standard polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #6	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2494.2	Semi standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #6	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2250.9	Standard non polar	33892256
Dimethylguanidino valeric acid,2TBDMS,isomer #6	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C	2787.6	Standard polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #1	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2652.7	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #1	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2178.3	Standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #1	CN(C)C(=N[Si](C)(C)C(C)(C)C)NCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2826.2	Standard polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #2	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2705.8	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #2	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2502.6	Standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #2	CN(C)C(=N)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2823.3	Standard polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #3	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2641.1	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #3	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2409.1	Standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #3	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2667.9	Standard polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #4	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2730.2	Semi standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #4	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2412.4	Standard non polar	33892256
Dimethylguanidino valeric acid,3TBDMS,isomer #4	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2784.9	Standard polar	33892256
Dimethylguanidino valeric acid,4TBDMS,isomer #1	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2863.4	Semi standard non polar	33892256
Dimethylguanidino valeric acid,4TBDMS,isomer #1	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2470.6	Standard non polar	33892256
Dimethylguanidino valeric acid,4TBDMS,isomer #1	CN(C)C(=N[Si](C)(C)C(C)(C)C)N(CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2662.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dimethylguanidino valeric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dimethylguanidino valeric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 10V, Positive-QTOF	splash10-0kai-1940000000-8834e2eb843b54e46534	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 20V, Positive-QTOF	splash10-015i-8900000000-084ea4e0508b724b125f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 40V, Positive-QTOF	splash10-0079-9000000000-502ae8943387e9814529	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 10V, Negative-QTOF	splash10-0udi-2490000000-89b68aa825543396110c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 20V, Negative-QTOF	splash10-0f79-9710000000-372fc2cbab2e10a6d8c9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 40V, Negative-QTOF	splash10-007c-9200000000-7dcc2da22dc6ddfd77d6	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 10V, Positive-QTOF	splash10-0udi-4690000000-82cd60e4bae9c5e7675a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 20V, Positive-QTOF	splash10-00y1-9200000000-c6a6719b25bc049176ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 40V, Positive-QTOF	splash10-00xv-9000000000-f69ec4af383dad51cbf2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 10V, Negative-QTOF	splash10-0udi-1390000000-4571d355661359f45481	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 20V, Negative-QTOF	splash10-01p9-8900000000-37ddb1733436eebef437	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimethylguanidino valeric acid 40V, Negative-QTOF	splash10-0159-9000000000-c2b5cce44192d475fcf4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0451 +/- 0.0213 uM	Adult (>18 years old)	Both	Normal	21945966	details
Urine	Detected and Quantified	0.162 (0.0114-1.03) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	21945966	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00033966

Chemspider ID

58779677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101535539

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Martens-Lobenhoffer J, Rodionov RN, Drust A, Bode-Boger SM: Detection and quantification of alpha-keto-delta-(N(G),N(G)-dimethylguanidino)valeric acid: a metabolite of asymmetric dimethylarginine. Anal Biochem. 2011 Dec 15;419(2):234-40. doi: 10.1016/j.ab.2011.08.044. Epub 2011 Sep 8. [PubMed:21945966 ]
O'Sullivan JF, Morningstar JE, Yang Q, Zheng B, Gao Y, Jeanfavre S, Scott J, Fernandez C, Zheng H, O'Connor S, Cohen P, Vasan RS, Long MT, Wilson JG, Melander O, Wang TJ, Fox C, Peterson RT, Clish CB, Corey KE, Gerszten RE: Dimethylguanidino valeric acid is a marker of liver fat and predicts diabetes. J Clin Invest. 2017 Dec 1;127(12):4394-4402. doi: 10.1172/JCI95995. Epub 2017 Oct 30. [PubMed:29083323 ]
Robbins JM, Herzig M, Morningstar J, Sarzynski MA, Cruz DE, Wang TJ, Gao Y, Wilson JG, Bouchard C, Rankinen T, Gerszten RE: Association of Dimethylguanidino Valeric Acid With Partial Resistance to Metabolic Health Benefits of Regular Exercise. JAMA Cardiol. 2019 Jul 1;4(7):636-643. doi: 10.1001/jamacardio.2019.1573. [PubMed:31166569 ]

Showing metabocard for Dimethylguanidino valeric acid (HMDB0240212)

MOL for HMDB0240212 (Dimethylguanidino valeric acid)

3D MOL for HMDB0240212 (Dimethylguanidino valeric acid)

3D SDF for HMDB0240212 (Dimethylguanidino valeric acid)

3D-SDF for HMDB0240212 (Dimethylguanidino valeric acid)

PDB for HMDB0240212 (Dimethylguanidino valeric acid)

3D PDB for HMDB0240212 (Dimethylguanidino valeric acid)

SMILES for HMDB0240212 (Dimethylguanidino valeric acid)

INCHI for HMDB0240212 (Dimethylguanidino valeric acid)

Structure for HMDB0240212 (Dimethylguanidino valeric acid)

3D Structure for HMDB0240212 (Dimethylguanidino valeric acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra