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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:56:01 UTC

HMDB ID

HMDB0001539

Secondary Accession Numbers

HMDB01539

Metabolite Identification

Common Name

Asymmetric dimethylarginine

Description

Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. It is a metabolic by-product of continual protein modification processes in the cytoplasm of all human cells. It is closely related to L-arginine, a conditionally-essential amino acid. ADMA interferes with L-arginine in the production of nitric oxide, a key chemical to endothelial and hence cardiovascular health. Asymmetric dimethylarginine is created in protein methylation, a common mechanism of post-translational protein modification. This reaction is catalyzed by an enzyme set called S-adenosylmethionine protein N-methyltransferases (protein methylases I and II). The methyl groups transferred to create ADMA are derived from the methyl group donor S-adenosylmethionine, an intermediate in the metabolism of homocysteine. (Homocysteine is an important blood chemical, because it is also a marker of cardiovascular disease). After synthesis, ADMA migrates into the extracellular space and thence into blood plasma. Asymmetric dimethylarginine is measured using high performance liquid chromatography. ADMA has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).

Structure

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

HMDB0001539
     RDKit          3D
Asymmetric dimethylarginine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -3.5224   -1.5696    0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4075   -0.1610    0.3519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5868    0.6606    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053    0.4074    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.9897   -0.9223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    0.3802    1.3346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172    0.9444    1.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    0.0204    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2856    0.5266    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -0.5029   -0.4113 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9158   -1.7675    0.2771 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4380   -0.1159   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244   -0.8919   -0.1807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478    1.0331   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944   -2.1416   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6928   -1.8655    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4918   -1.8028    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    0.7243    1.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2928    1.6913   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2046    0.2262   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239    1.9958   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.4140   -1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0277    1.9559    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    0.8966    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -0.0342   -0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -0.9709    0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.5226   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    0.5106    1.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742   -0.5500   -1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -1.6816    1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -2.5711   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4472    1.7265   -0.7970 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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
  5 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
 10 29  1  6
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

  Mrv0541 02231215392D          

 14 13  0  0  1  0            999 V2000
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  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  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001539

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
YDGMGEXADBMOMJ-LURJTMIESA-N

> <FORMULA>
C8H18N4O2

> <MOLECULAR_WEIGHT>
202.2541

> <EXACT_MASS>
202.14297584

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.186030281533142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid

> <ALOGPS_LOGP>
-3.13

> <JCHEM_LOGP>
-2.6729980412943983

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.539262506302749

> <JCHEM_PKA_STRONGEST_BASIC>
12.34050755300345

> <JCHEM_POLAR_SURFACE_AREA>
104.94

> <JCHEM_REFRACTIVITY>
53.699600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asymmetric dimethylarginine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001539
     RDKit          3D
Asymmetric dimethylarginine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -3.5224   -1.5696    0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4075   -0.1610    0.3519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5868    0.6606    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053    0.4074    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.9897   -0.9223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    0.3802    1.3346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172    0.9444    1.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    0.0204    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2856    0.5266    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -0.5029   -0.4113 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9158   -1.7675    0.2771 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4380   -0.1159   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244   -0.8919   -0.1807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478    1.0331   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944   -2.1416   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6928   -1.8655    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4918   -1.8028    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    0.7243    1.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2928    1.6913   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2046    0.2262   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239    1.9958   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.4140   -1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0277    1.9559    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    0.8966    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -0.0342   -0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -0.9709    0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.5226   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    0.5106    1.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742   -0.5500   -1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -1.6816    1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -2.5711   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4472    1.7265   -0.7970 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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
  5 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
 10 29  1  6
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.953   7.287   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.953   5.747   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.619   4.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.620   5.747   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.286   3.437   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0001539
HETATM    1  C1  UNL     1      -3.522  -1.570   0.616  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.408  -0.161   0.352  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.587   0.661   0.157  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.105   0.407   0.287  1.00  0.00           C  
HETATM    5  N2  UNL     1      -1.659   0.990  -0.922  1.00  0.00           N  
HETATM    6  N3  UNL     1      -1.356   0.380   1.335  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.017   0.944   1.329  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.849   0.020   0.510  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.286   0.527   0.441  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.033  -0.503  -0.411  1.00  0.00           C  
HETATM   11  N4  UNL     1       2.916  -1.767   0.277  1.00  0.00           N  
HETATM   12  C8  UNL     1       4.438  -0.116  -0.611  1.00  0.00           C  
HETATM   13  O1  UNL     1       5.324  -0.892  -0.181  1.00  0.00           O  
HETATM   14  O2  UNL     1       4.848   1.033  -1.234  1.00  0.00           O  
HETATM   15  H1  UNL     1      -3.394  -2.142  -0.315  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.693  -1.866   1.316  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.492  -1.803   1.133  1.00  0.00           H  
HETATM   18  H4  UNL     1      -5.192   0.724   1.102  1.00  0.00           H  
HETATM   19  H5  UNL     1      -4.293   1.691  -0.100  1.00  0.00           H  
HETATM   20  H6  UNL     1      -5.205   0.226  -0.644  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.424   1.996  -0.945  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.571   0.414  -1.770  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.028   1.956   0.916  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.351   0.897   2.372  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.453  -0.034  -0.528  1.00  0.00           H  
HETATM   26  H12 UNL     1       0.890  -0.971   0.978  1.00  0.00           H  
HETATM   27  H13 UNL     1       2.322   1.523  -0.011  1.00  0.00           H  
HETATM   28  H14 UNL     1       2.732   0.511   1.454  1.00  0.00           H  
HETATM   29  H15 UNL     1       2.474  -0.550  -1.377  1.00  0.00           H  
HETATM   30  H16 UNL     1       3.315  -1.682   1.234  1.00  0.00           H  
HETATM   31  H17 UNL     1       3.267  -2.571  -0.267  1.00  0.00           H  
HETATM   32  H18 UNL     1       5.447   1.726  -0.797  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4
CONECT    3   18   19   20
CONECT    4    5    6    6
CONECT    5   21   22
CONECT    6    7
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   12   29
CONECT   11   30   31
CONECT   12   13   13   14
CONECT   14   32
END

HMDB0001539
     RDKit          3D
Asymmetric dimethylarginine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -3.5224   -1.5696    0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4075   -0.1610    0.3519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5868    0.6606    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053    0.4074    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6592    0.9897   -0.9223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    0.3802    1.3346 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172    0.9444    1.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    0.0204    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2856    0.5266    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327   -0.5029   -0.4113 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9158   -1.7675    0.2771 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4380   -0.1159   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244   -0.8919   -0.1807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478    1.0331   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944   -2.1416   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6928   -1.8655    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4918   -1.8028    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    0.7243    1.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2928    1.6913   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2046    0.2262   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239    1.9958   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.4140   -1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0277    1.9559    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3506    0.8966    2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -0.0342   -0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -0.9709    0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.5226   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322    0.5106    1.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742   -0.5500   -1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151   -1.6816    1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -2.5711   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4472    1.7265   -0.7970 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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
  5 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
 10 29  1  6
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
ADMA	ChEBI
Guanidino-N,N-dimethylarginine	ChEBI
N,N-Dimethylarginine	ChEBI
N(5)-((Dimethylamino)iminomethyl)-L-ornithine	ChEBI
NG,NG-Dimethyl-L-arginine	ChEBI
N(g),N(g)-Dimethylarginine	ChEBI
N(g)-Dimethylarginine	ChEBI
N(g1),N(g1)-Dimethylarginine	ChEBI
Nomega,nomega-dimethyl-L-arginine	Kegg
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoate	HMDB
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid	HMDB
Dimethyl-L-arginine	HMDB
N(Omega),N(omega)-dimethyl-L-arginine	HMDB
NG,NG-Dimethylarginine	HMDB
NG-Dimethylarginine	HMDB
Nomega,nomega'-dimethyl-L-arginine	HMDB
Asymmetric dimethylarginine	ChEBI

Chemical Formula

C₈H₁₈N₄O₂

Average Molecular Weight

202.2541

Monoisotopic Molecular Weight

202.14297584

IUPAC Name

(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid

Traditional Name

asymmetric dimethylarginine

CAS Registry Number

30315-93-6

SMILES

N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O

InChI Identifier

InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1

InChI Key

YDGMGEXADBMOMJ-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Arginine and derivatives

Alternative Parents

Substituents

Arginine or derivatives
Alpha-amino acid
L-alpha-amino acid
Fatty acid
Guanidine
Amino acid
Carboximidamide
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Imine
Carbonyl group
Amine
Organic nitrogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:17929 )
non-proteinogenic L-alpha-amino acid (CHEBI:17929 )
L-arginine derivative (CHEBI:17929 )
dimethylarginine (CHEBI:17929 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)
Coma (HMDB: HMDB0001539)

Central nervous system disorder

Psychiatric disorder

Psychosis (HMDB: HMDB0001539)

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0001539)
Uremia (HMDB: HMDB0001539)
Chronic kidney disease (HMDB: HMDB0001539)

Circulatory system disorder

Cardiac disorder

Essential hypertension (HMDB: HMDB0001539)
Cardiovascular disease (HMDB: HMDB0001539)

Musculoskeletal system disorder

Skeletal system disorder

Spinal stenosis (HMDB: HMDB0001539)
Spinal disc herniation (HMDB: HMDB0001539)

Observation

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16217682)
Cerebrospinal Fluid (CSF) (PMID: 17512604)
Cerebrospinal fluid (HMDB: HMDB0001539)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 16384887)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0001539)
Membrane (HMDB: HMDB0001539)

Organelle

Mitochondrion (HMDB: HMDB0001539)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0001539)

Enteral

Ingestion (HMDB: HMDB0001539)

Source

Exogenous

Exogenous (HMDB: HMDB0001539)

Food

Food (HMDB: HMDB0001539)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Broccoli (FooDB: FOOD00034)
White cabbage (FooDB: FOOD00887)

Leaf vegetable

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Oat (FooDB: FOOD00022)
Rye (FooDB: FOOD00169)
Wheat (FooDB: FOOD00561)

Gourd

Cucumber (FooDB: FOOD00065)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Turnip (FooDB: FOOD00036)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Pulses (FooDB: FOOD00867)

Endogenous

Endogenous (HMDB: HMDB0001539)

Plant

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001539)

Biomarker

Kidney disease (MarkerDB: MDB00013441)
Chronic kidney disease (MarkerDB: MDB00013441)
Autosomal dominant polycystic kidney disease (MarkerDB: MDB00013441)
Hypertension (MarkerDB: MDB00013441)

Biological role

Modulator

Inhibitor

EC 1.14.13.39 (nitric oxide synthase) inhibitor (HMDB: HMDB0001539)

Waste product (PMID: 35448883)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 - 197 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	147.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000092
[M+H]+	Not Available	143.615	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000092

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.52 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-2.7	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	12.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.7 m³·mol⁻¹	ChemAxon
Polarizability	22.19 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
DarkChem	[M+H]+	148.711	31661259
DarkChem	[M-H]-	146.422	31661259
AllCCS	[M+H]+	146.974	32859911
AllCCS	[M-H]-	146.72	32859911
DeepCCS	[M+H]+	149.26	30932474
DeepCCS	[M-H]-	146.902	30932474
DeepCCS	[M-2H]-	182.024	30932474
DeepCCS	[M+Na]+	157.034	30932474
AllCCS	[M+H]+	147.0	32859911
AllCCS	[M+H-H2O]+	143.4	32859911
AllCCS	[M+NH4]+	150.3	32859911
AllCCS	[M+Na]+	151.2	32859911
AllCCS	[M-H]-	146.7	32859911
AllCCS	[M+Na-2H]-	148.0	32859911
AllCCS	[M+HCOO]-	149.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Asymmetric dimethylarginine	N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O	2752.8	Standard polar	33892256
Asymmetric dimethylarginine	N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O	1723.6	Standard non polar	33892256
Asymmetric dimethylarginine	N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O	2237.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Asymmetric dimethylarginine,1TMS,isomer #1	CN(C)/C(N)=N/CCC[C@H](N)C(=O)O[Si](C)(C)C	1948.3	Semi standard non polar	33892256
Asymmetric dimethylarginine,1TMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O	2065.9	Semi standard non polar	33892256
Asymmetric dimethylarginine,1TMS,isomer #3	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N[Si](C)(C)C	2070.2	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #1	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	2015.0	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #1	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	1856.0	Standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #1	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	3352.1	Standard polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1987.5	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1862.0	Standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	3456.2	Standard polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #3	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N[Si](C)(C)C	2083.1	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #3	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N[Si](C)(C)C	1838.2	Standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #3	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N[Si](C)(C)C	3286.5	Standard polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #4	CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2122.2	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #4	CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1973.5	Standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #4	CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3609.1	Standard polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #5	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2098.1	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #5	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1958.9	Standard non polar	33892256
Asymmetric dimethylarginine,2TMS,isomer #5	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3554.1	Standard polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #1	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	2066.2	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #1	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	1903.6	Standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #1	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	2882.7	Standard polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #2	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2061.0	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #2	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2035.3	Standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #2	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3010.2	Standard polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #3	CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2122.3	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #3	CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2012.5	Standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #3	CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3382.2	Standard polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #4	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2191.9	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #4	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	1982.4	Standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #4	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	3002.2	Standard polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #5	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2131.8	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #5	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2033.5	Standard non polar	33892256
Asymmetric dimethylarginine,3TMS,isomer #5	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2837.2	Standard polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2197.1	Semi standard non polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2008.5	Standard non polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N[Si](C)(C)C	2704.0	Standard polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #2	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2126.1	Semi standard non polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #2	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2061.6	Standard non polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #2	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2486.9	Standard polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #3	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2225.3	Semi standard non polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #3	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2158.9	Standard non polar	33892256
Asymmetric dimethylarginine,4TMS,isomer #3	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2609.0	Standard polar	33892256
Asymmetric dimethylarginine,5TMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2296.3	Semi standard non polar	33892256
Asymmetric dimethylarginine,5TMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2156.7	Standard non polar	33892256
Asymmetric dimethylarginine,5TMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2378.1	Standard polar	33892256
Asymmetric dimethylarginine,1TBDMS,isomer #1	CN(C)/C(N)=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2142.3	Semi standard non polar	33892256
Asymmetric dimethylarginine,1TBDMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2265.0	Semi standard non polar	33892256
Asymmetric dimethylarginine,1TBDMS,isomer #3	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N[Si](C)(C)C(C)(C)C	2285.0	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #1	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2408.8	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #1	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2240.4	Standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #1	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3315.5	Standard polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2379.2	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2298.0	Standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #2	CN(C)/C(N)=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3501.2	Standard polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #3	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N[Si](C)(C)C(C)(C)C	2514.6	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #3	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N[Si](C)(C)C(C)(C)C	2225.6	Standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #3	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N[Si](C)(C)C(C)(C)C	3196.9	Standard polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #4	CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2528.1	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #4	CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2393.3	Standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #4	CN(C)/C(N)=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3599.5	Standard polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #5	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2496.2	Semi standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #5	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2368.9	Standard non polar	33892256
Asymmetric dimethylarginine,2TBDMS,isomer #5	CN(C)/C(=N/CCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3384.2	Standard polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #1	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2666.4	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #1	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2441.0	Standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #1	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2967.2	Standard polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #2	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2656.6	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #2	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2590.6	Standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #2	CN(C)/C(=N/CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3046.1	Standard polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #3	CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2749.0	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #3	CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2624.3	Standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #3	CN(C)/C(N)=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3454.9	Standard polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #4	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2801.9	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #4	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2530.4	Standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #4	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3043.0	Standard polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #5	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2743.3	Semi standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #5	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2593.5	Standard non polar	33892256
Asymmetric dimethylarginine,3TBDMS,isomer #5	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2922.7	Standard polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	3024.5	Semi standard non polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2709.7	Standard non polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	2944.6	Standard polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #2	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2910.8	Semi standard non polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #2	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2754.9	Standard non polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #2	CN(C)/C(=N/CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2805.1	Standard polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #3	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3045.8	Semi standard non polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #3	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2855.9	Standard non polar	33892256
Asymmetric dimethylarginine,4TBDMS,isomer #3	CN(C)/C(=N/CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2859.8	Standard polar	33892256
Asymmetric dimethylarginine,5TBDMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3246.4	Semi standard non polar	33892256
Asymmetric dimethylarginine,5TBDMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3004.4	Standard non polar	33892256
Asymmetric dimethylarginine,5TBDMS,isomer #1	CN(C)/C(=N/CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2792.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Asymmetric dimethylarginine GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Asymmetric dimethylarginine GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asymmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9300000000-4fc2a444d078a1eb4d85	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asymmetric dimethylarginine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9520000000-928759e33b3f9821da4a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asymmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asymmetric dimethylarginine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Asymmetric dimethylarginine 35V, Negative-QTOF	splash10-0006-9100000000-2849c1945541be90da8a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Asymmetric dimethylarginine 35V, Positive-QTOF	splash10-00di-9200000000-f7af59f4a85b35ee2239	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Asymmetric dimethylarginine 35V, Positive-QTOF	splash10-00di-9310000000-901ceea58124eb646d2d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Positive-QTOF	splash10-0pbi-1930000000-6a12bc30dbe08d316d09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Positive-QTOF	splash10-0abi-8900000000-47e0a5a868dce918c9b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Positive-QTOF	splash10-00di-9000000000-d674ec18daa47f080be4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Negative-QTOF	splash10-0udi-3390000000-2b624585e91010265a57	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Negative-QTOF	splash10-0f79-9420000000-b8fe15104f41182b9d9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Negative-QTOF	splash10-00dl-9100000000-120212bd5d151152c8ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Negative-QTOF	splash10-0uk9-9370000000-4bea91f4d0256a94739f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Negative-QTOF	splash10-01si-2900000000-8fc254a7c96b0565c1ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Negative-QTOF	splash10-0006-9200000000-428e5ae3fbdfa34b338c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 10V, Positive-QTOF	splash10-0udr-2690000000-5766392f870c77d53359	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 20V, Positive-QTOF	splash10-00dr-9200000000-a7b438425f1f49a1a48b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asymmetric dimethylarginine 40V, Positive-QTOF	splash10-00di-9000000000-e6f7e053fa2072aa45ff	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Kidney
Liver
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.30-1.00 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.61 +/- 0.13 uM	Adult (>18 years old)	Both	Normal	31726035	details
Blood	Detected and Quantified	0.595 +/- 0.129 uM	Children (1-13 years old)	Male	Normal	26066683	details
Blood	Detected and Quantified	<0.30 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected and Quantified	0.35 (0.28-0.42) uM	Adult (>18 years old)	Both	Normal	16217682	details
Blood	Detected and Quantified	0.88(0.72-1.03) uM	Children (1-13 uears old)	Both	Normal	27294788	details
Blood	Detected and Quantified	0989 +/- 0.297 uM	Adult (>18 years old)	Both	Normal	12675874	details
Blood	Detected and Quantified	0.45 +/- 0.11 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	0.66 +/- 0.04 uM	Adult (>18 years old)	Both	Normal	14500028	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.06 +/- 0.008 uM	Adult (>18 years old)	Both	Normal	17512604	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.13 +/- 0.074 uM	Adult (>18 years old)	Both	Normal	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	8.86 +/- 12.1 umol/mmol creatinine	Children (1-13 years old)	Male	Normal	26066683	details
Urine	Detected and Quantified	2.92 +/- 0.42 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16384887	details
Urine	Detected and Quantified	0.98-4.87 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	2.34 +/- 0.52 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	2.3 +/- 0.97 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	4.6 (3.00-7.00) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	5472370	details
Urine	Detected and Quantified	15.2 +/- 3.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	18215696	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	2.7 (1.4-4.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	3.0 (0.2-6.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	5.76 (4.47-7.58) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	4.35 +/- 0.19 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected and Quantified	0.60 +/- 0.14 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Blood	Detected and Quantified	0.60 +/- 0.14 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Blood	Detected and Quantified	0.60 +/- 0.14 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Blood	Detected and Quantified	0.631 +/- 0.119 uM	Children (1-13 years old)	Male	Duchenne Muscular Dystrophy	26066683	details
Blood	Detected and Quantified	2.40 (1.30-3.50) uM	Adult (>18 years old)	Both	Essential hypertension	10218738	details
Blood	Detected and Quantified	0.92(0.75-1.13) uM	Children (1-13 uears old)	Both	Environmental enteric dysfunction	27294788	details
Blood	Detected and Quantified	0.00792 +/- 0.00594 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Blood	Detected and Quantified	0.91 +/- 0.04 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	1.04 +/- 0.04 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	0.87 +/- 0.04 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	0.97 +/- 0.02 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.11 +/- 0.049 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.12 +/- 0.033 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.072 +/- 0.019 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected and Quantified	20.3 +/- 10.2 umol/mmol creatinine	Children (1-13 years old)	Male	Duchenne Muscular Dystrophy	26066683	details
Urine	Detected and Quantified	22.0 +/- 4.0 umol/mmol creatinine	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	18215696	details

Associated Disorders and Diseases

Disease References

Essential hypertension
Surdacki A, Nowicki M, Sandmann J, Tsikas D, Boeger RH, Bode-Boeger SM, Kruszelnicka-Kwiatkowska O, Kokot F, Dubiel JS, Froelich JC: Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension. J Cardiovasc Pharmacol. 1999 Apr;33(4):652-8. [PubMed:10218738 ]
Kidney disease
Fleck C, Schweitzer F, Karge E, Busch M, Stein G: Serum concentrations of asymmetric (ADMA) and symmetric (SDMA) dimethylarginine in patients with chronic kidney diseases. Clin Chim Acta. 2003 Oct;336(1-2):1-12. [PubMed:14500028 ]
Uremia
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 ] 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 ]
Duchenne Muscular Dystrophy
Horster I, Weigt-Usinger K, Carmann C, Chobanyan-Jurgens K, Kohler C, Schara U, Kayacelebi AA, Beckmann B, Tsikas D, Lucke T: The L-arginine/NO pathway and homoarginine are altered in Duchenne muscular dystrophy and improved by glucocorticoids. Amino Acids. 2015 Sep;47(9):1853-63. doi: 10.1007/s00726-015-2018-x. Epub 2015 Jun 12. [PubMed:26066683 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Autosomal dominant polycystic kidney disease
Wang D, Strandgaard S, Borresen ML, Luo Z, Connors SG, Yan Q, Wilcox CS: Asymmetric dimethylarginine and lipid peroxidation products in early autosomal dominant polycystic kidney disease. Am J Kidney Dis. 2008 Feb;51(2):184-91. doi: 10.1053/j.ajkd.2007.09.020. [PubMed:18215696 ]

Associated OMIM IDs

310200 (Duchenne Muscular Dystrophy)
114500 (Colorectal cancer)
601313 (Autosomal dominant polycystic kidney disease)

External Links

DrugBank ID

DB01686

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000508

KNApSAcK ID

Not Available

Chemspider ID

110375

KEGG Compound ID

C03626

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Asymmetric dimethylarginine

METLIN ID

6309

PubChem Compound

123831

PDB ID

Not Available

ChEBI ID

17929

Food Biomarker Ontology

Not Available

VMH ID

DMLARG

MarkerDB ID

MDB00013441

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

van Guldener C, Nanayakkara PW, Stehouwer CD: Homocysteine and asymmetric dimethylarginine (ADMA): biochemically linked but differently related to vascular disease in chronic kidney disease. Clin Chem Lab Med. 2007;45(12):1683-7. [PubMed:17937610 ]
Surdacki A, Nowicki M, Sandmann J, Tsikas D, Boeger RH, Bode-Boeger SM, Kruszelnicka-Kwiatkowska O, Kokot F, Dubiel JS, Froelich JC: Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension. J Cardiovasc Pharmacol. 1999 Apr;33(4):652-8. [PubMed:10218738 ]
Martens-Lobenhoffer J, Bode-Boger SM: Measurement of asymmetric dimethylarginine (ADMA) in human plasma: from liquid chromatography estimation to liquid chromatography-mass spectrometry quantification. Eur J Clin Pharmacol. 2006 Feb;62(Supplement 13):61-68. [PubMed:16217682 ]
Watanabe T, Kato S, Sato K, Nagata K: Nitric oxide regulation system in degenerative lumbar disease. Kurume Med J. 2005;52(1-2):39-47. [PubMed:16119611 ]
Nijveldt RJ, Teerlink T, Siroen MP, van der Hoven B, Prins HA, Wiezer MJ, Meijer C, van der Sijp JR, Cuesta MA, Meijer S, van Leeuwen PA: Elevation of asymmetric dimethylarginine (ADMA) in patients developing hepatic failure after major hepatectomy. JPEN J Parenter Enteral Nutr. 2004 Nov-Dec;28(6):382-7. [PubMed:15568284 ]
Siroen MP, Warle MC, Teerlink T, Nijveldt RJ, Kuipers EJ, Metselaar HJ, Tilanus HW, Kuik DJ, van der Sijp JR, Meijer S, van der Hoven B, van Leeuwen PA: The transplanted liver graft is capable of clearing asymmetric dimethylarginine. Liver Transpl. 2004 Dec;10(12):1524-30. [PubMed:15558588 ]
Tarnow L, Hovind P, Teerlink T, Stehouwer CD, Parving HH: Elevated plasma asymmetric dimethylarginine as a marker of cardiovascular morbidity in early diabetic nephropathy in type 1 diabetes. Diabetes Care. 2004 Mar;27(3):765-9. [PubMed:14988299 ]
Wang J, Sim AS, Wang XL, Salonikas C, Naidoo D, Wilcken DE: Relations between plasma asymmetric dimethylarginine (ADMA) and risk factors for coronary disease. Atherosclerosis. 2006 Feb;184(2):383-8. Epub 2005 Jun 6. [PubMed:15939423 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. N(G),N(G)-dimethylarginine dimethylaminohydrolase 1

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:: Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:: DDAH1
Uniprot ID:: O94760
Molecular weight:: 20189.135

Reactions

Asymmetric dimethylarginine + Water → Dimethylamine + Citrulline	details

Enzyme Details

2. N(G),N(G)-dimethylarginine dimethylaminohydrolase 2

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:: Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:: DDAH2
Uniprot ID:: O95865
Molecular weight:: 29643.54

Reactions

Asymmetric dimethylarginine + Water → Dimethylamine + Citrulline	details

Enzyme Details

3. Nitric oxide synthase, inducible

General function:: Involved in oxidoreductase activity
Specific function:: Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:: NOS2
Uniprot ID:: P35228
Molecular weight:: 131116.3

References

van Guldener C, Nanayakkara PW, Stehouwer CD: Homocysteine and asymmetric dimethylarginine (ADMA): biochemically linked but differently related to vascular disease in chronic kidney disease. Clin Chem Lab Med. 2007;45(12):1683-7. [PubMed:17937610 ]

Enzyme Details

4. Nitric oxide synthase, endothelial

General function:: Involved in oxidoreductase activity
Specific function:: Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets. Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
Gene Name:: NOS3
Uniprot ID:: P29474
Molecular weight:: 133273.59

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Showing metabocard for Asymmetric dimethylarginine (HMDB0001539)

MOL for HMDB0001539 (Asymmetric dimethylarginine)

3D MOL for HMDB0001539 (Asymmetric dimethylarginine)

3D SDF for HMDB0001539 (Asymmetric dimethylarginine)

3D-SDF for HMDB0001539 (Asymmetric dimethylarginine)

PDB for HMDB0001539 (Asymmetric dimethylarginine)

3D PDB for HMDB0001539 (Asymmetric dimethylarginine)

SMILES for HMDB0001539 (Asymmetric dimethylarginine)

INCHI for HMDB0001539 (Asymmetric dimethylarginine)

Structure for HMDB0001539 (Asymmetric dimethylarginine)

3D Structure for HMDB0001539 (Asymmetric dimethylarginine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

References

References