MiMeDB: Showing metabocard for Asymmetric dimethylarginine (MMDBc0000571)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:48 UTC

Update Date

2024-10-13 11:36:32 UTC

Metabolite ID

MMDBc0000571

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>
MMDBc0000571

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₈H₁₈N₄O₂

Average Mass

202.2541

Monoisotopic Mass

202.14297584

IUPAC Name

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

Traditional Name

asymmetric dimethylarginine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.77 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Kidney
Liver
Placenta
Urine

Tissue Locations

Kidney
Liver
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192389	N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Unknown	O94760	Homo sapiens
MMDBp0192390	N(G),N(G)-dimethylarginine dimethylaminohydrolase 2	Enzyme	O95865	Homo sapiens
MMDBp0192544	Nitric oxide synthase, inducible	Unknown	P35228	Homo sapiens
MMDBp0192547	Nitric oxide synthase, endothelial	Unknown	P29474	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Essential hypertension		Association	Human Blood	HMDB	10218738
Kidney disease		Association	Human Blood	HMDB	14500028
Uremia	Decreased	Association	Human Blood	HMDB	12675874
Uremia		Association	Human Blood	HMDB	22626821

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	45	Human stool; Human ; Human feces; Human urine; Human sputum; Human saliva; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Actinobacteria	18	Human ; Human supragingival plaque; Human subgingival plaque; Human feces; Human sputum; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	15	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	16	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	2	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	3	Human ; Human supragingival plaque; Human subgingival plaque; Human feces; Human sputum; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	2	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	22.0	4.0			umol/mmol creatinine	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	HMDB	18215696
Human Blood	Detected and Quantified	0.631	0.119			uM	Children (1-13 years old)	Male	Duchenne Muscular Dystrophy	HMDB	26066683
Human Urine	Detected and Quantified	20.3	10.2			umol/mmol creatinine	Children (1-13 years old)	Male	Duchenne Muscular Dystrophy	HMDB	26066683
Human Blood	Detected and Quantified	2.40		1.30	3.50	uM	Adult (>18 years old)	Both	Essential hypertension	HMDB	10218738
Human Blood	Detected and Quantified	0.87	0.04			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	0.91	0.04			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	0.97	0.02			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	1.04	0.04			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	0.00792	0.00594			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	4.35	0.19			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	<0.30				uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.06	0.008			uM	Adult (>18 years old)	Both	Normal	HMDB	17512604
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.13	0.074			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Blood	Detected and Quantified	0.45	0.11			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	0.595	0.129			uM	Children (1-13 years old)	Male	Normal	HMDB	26066683
Human Blood	Detected and Quantified	0.61	0.13			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Blood	Detected and Quantified	0.66	0.04			uM	Adult (>18 years old)	Both	Normal	HMDB	14500028
Human Blood	Detected and Quantified	0.88		0.72	1.03	uM	Children (1-13 uears old)	Both	Normal	HMDB	27294788
Human Urine	Detected and Quantified			0.98	4.87	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0989	0.297			uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Urine	Detected and Quantified	15.2	3.0			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18215696
Human Urine	Detected and Quantified	2.3	0.97			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	2.34	0.52			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	2.7		1.4	4.2	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	2.92	0.42			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16384887
Human Urine	Detected and Quantified	3.0		0.2	6.7	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	4.6		3.00	7.00	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	5472370
Human Urine	Detected and Quantified	8.86	12.1			umol/mmol creatinine	Children (1-13 years old)	Male	Normal	HMDB	26066683
Human Blood	Detected and Quantified			0.30	1.00	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001539

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1097/00005344-199904000-00020. [PubMed:10218738 ]
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. doi: 10.2337/diacare.27.3.765. [PubMed:14988299 ]
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. doi: 10.1002/lt.20286. [PubMed:15558588 ]
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. doi: 10.1177/0148607104028006382. [PubMed:15568284 ]
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. doi: 10.1016/j.atherosclerosis.2005.05.002. Epub 2005 Jun 6. [PubMed:15939423 ]
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. doi: 10.2739/kurumemedj.52.39. [PubMed:16119611 ]
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. doi: 10.1515/CCLM.2007.340. [PubMed:17937610 ]
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 ]
Martens-Lobenhoffer J, Bode-Boger SM (2006). 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. . Eur J Clin Pharmacol..

Showing metabocard for Asymmetric dimethylarginine (MMDBc0000571)

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