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

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6w-1920000000-352e317361bed495b71b	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9300000000-4fc2a444d078a1eb4d85	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9520000000-928759e33b3f9821da4a	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9100000000-2849c1945541be90da8a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9200000000-f7af59f4a85b35ee2239	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9310000000-901ceea58124eb646d2d	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pbi-1930000000-6a12bc30dbe08d316d09	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-8900000000-47e0a5a868dce918c9b7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-d674ec18daa47f080be4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3390000000-2b624585e91010265a57	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-9420000000-b8fe15104f41182b9d9b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9100000000-120212bd5d151152c8ad	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-9370000000-4bea91f4d0256a94739f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-2900000000-8fc254a7c96b0565c1ff	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-428e5ae3fbdfa34b338c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-2690000000-5766392f870c77d53359	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9200000000-a7b438425f1f49a1a48b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-e6f7e053fa2072aa45ff	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

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
MMDBr0008371	Asymmetric dimethylarginine	Citrulline	Not Available		VMH	30371894
MMDBr0010689	Asymmetric dimethylarginine	Citrulline	dimethylarginine dimethylaminohydrolase 1		VMH; KEGG	30371894

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	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	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	Actinobacteria	21	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	Bacteroidetes	15	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Proteobacteria	18	Human feces; Human	Metabolic reconstruction
Bacteria	Fusobacteria	2	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant		Solanum tuberosum	FooDB	31437929
Plant		Allium cepa	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant		Beta vulgaris ssp. cicla	FooDB	31437929
Plant		Rubus idaeus	FooDB	31437929
Plant		Cucurbita pepo var. clypeata	FooDB	31437929
Plant		Spinacia oleracea	FooDB	31437929
Plant		Cucurbita pepo var. cylindrica	FooDB	31437929
Plant		Beta vulgaris var. rubra	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Pastinaca sativa	FooDB	31437929
Plant		Cucumis sativus	FooDB	31437929
Plant		Lactuca sativa l. var. longifolia	FooDB	31437929
Plant		Cucurbita maxima	FooDB	31437929
Plant		Amelanchier alnifolia	FooDB	31437929
Plant		Prunus tomentosa	FooDB	31437929
Plant		Pastinaca sativa	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Anethum graveolens	FooDB	31437929
Plant		Brassica rapa var. rapa	FooDB	31437929
Plant		Daucus carota ssp. sativus	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929
Plant		Solanum melongena	FooDB	31437929
Plant		Capsicum annuum	FooDB	31437929

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 ]
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Showing metabocard for Asymmetric dimethylarginine (MMDBc0000571)

MOL for #<Metabolite:0x00007f46d2f66330>

3D MOL for #<Metabolite:0x00007f46d2f66330>

3D SDF for #<Metabolite:0x00007f46d2f66330>

3D-SDF for #<Metabolite:0x00007f46d2f66330>

PDB for #<Metabolite:0x00007f46d2f66330>

3D PDB for #<Metabolite:0x00007f46d2f66330>

SMILES for #<Metabolite:0x00007f46d2f66330>

INCHI for #<Metabolite:0x00007f46d2f66330>

Structure for #<Metabolite:0x00007f46d2f66330>

3D Structure for #<Metabolite:0x00007f46d2f66330>