MiMeDB: Showing metabocard for Symmetric dimethylarginine (MMDBc0000572)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:49 UTC

Update Date

2024-10-15 18:17:31 UTC

Metabolite ID

MMDBc0000572

Metabolite Identification

Common Name

Symmetric dimethylarginine

Description

Symmetric dimethylarginine, also known as N,n'-dimethylarginine or SDMA, is a L-arginine derivative having two methyl groups at the N(omega)- and N'(omega)-positions It has a role as an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a member of guanidines, a non-proteinogenic L-alpha-amino acid, a L-arginine derivative and a dimethylarginine. It is a tautomer of a N(omega),N'(omega)-dimethyl-L-arginine zwitterion. It 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. Symmetric dimethylarginine is a drug. Outside of the human body, symmetric dimethylarginine has been detected, but not quantified in pulses. Symmetric dimethylarginine (SDMA) is an endogenously produced inhibitor of nitric oxide synthase (EC-Number 1.14.13.39). However, elevated levels of Symmetric dimethylarginine occur in patients with vascular disease, especially suffering end-stage renal disease.

Structure

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

HMDB0003334
     RDKit          3D
Symmetric dimethylarginine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.9330   -0.4911    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.9474    0.9961 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830   -0.3994    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035    0.6103   -0.5657 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522    1.9758   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -0.8141    0.7503 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436   -0.1579    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639   -0.7244    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700    0.0301   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435   -0.4592    0.2905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8024   -1.8748   -0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6359    0.3486   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4472   -0.2220   -1.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6751    1.7114   -0.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021    0.5805    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7019   -1.0651    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -0.5814   -0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117    0.3647   -1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    2.2168   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2171    2.0661    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455    2.6465   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1053   -1.5781    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -0.3309   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    0.9099    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2559   -0.5345    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2488   -1.8097    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -0.1173   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1824    1.0877    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -0.2793    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8325   -2.0478   -0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   -2.4306    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024    2.3169   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  3  6  1  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
  4 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END


  Mrv1652305271900292D          

 14 13  0  0  1  0            999 V2000
   -0.3829    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   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
    1.0461    0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    0.1914    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  3 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000572

> <DATABASE_NAME>
MIME

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

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

> <INCHI_KEY>
HVPFXCBJHIIJGS-LURJTMIESA-N

> <FORMULA>
C8H18N4O2

> <MOLECULAR_WEIGHT>
202.2541

> <EXACT_MASS>
202.14297584

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.224320554292085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-[(E)-N',N''-dimethylcarbamimidamido]pentanoic acid

> <ALOGPS_LOGP>
-2.94

> <JCHEM_LOGP>
-2.654929684285306

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5397284499921273

> <JCHEM_PKA_STRONGEST_BASIC>
12.401054141729825

> <JCHEM_POLAR_SURFACE_AREA>
99.74

> <JCHEM_REFRACTIVITY>
53.179500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N3, N4-dimethylarginine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003334
     RDKit          3D
Symmetric dimethylarginine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.9330   -0.4911    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.9474    0.9961 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830   -0.3994    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035    0.6103   -0.5657 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522    1.9758   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -0.8141    0.7503 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436   -0.1579    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639   -0.7244    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700    0.0301   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435   -0.4592    0.2905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8024   -1.8748   -0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6359    0.3486   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4472   -0.2220   -1.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6751    1.7114   -0.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021    0.5805    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7019   -1.0651    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -0.5814   -0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117    0.3647   -1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    2.2168   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2171    2.0661    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455    2.6465   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1053   -1.5781    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -0.3309   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    0.9099    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2559   -0.5345    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2488   -1.8097    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -0.1173   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1824    1.0877    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -0.2793    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8325   -2.0478   -0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   -2.4306    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024    2.3169   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  3  6  1  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
  4 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.715   2.667   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.619   3.437   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.286   3.437   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       1.953   1.127   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.619   0.357   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0003334
HETATM    1  C1  UNL     1       4.933  -0.491   0.615  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.614  -0.947   0.996  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.583  -0.399   0.410  1.00  0.00           C  
HETATM    4  N2  UNL     1       2.804   0.610  -0.566  1.00  0.00           N  
HETATM    5  C3  UNL     1       3.152   1.976  -0.222  1.00  0.00           C  
HETATM    6  N3  UNL     1       1.259  -0.814   0.750  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.144  -0.158   0.122  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.164  -0.724   0.601  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.270   0.030  -0.116  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.644  -0.459   0.290  1.00  0.00           C  
HETATM   11  N4  UNL     1      -3.802  -1.875  -0.023  1.00  0.00           N  
HETATM   12  C8  UNL     1      -4.636   0.349  -0.447  1.00  0.00           C  
HETATM   13  O1  UNL     1      -5.447  -0.222  -1.205  1.00  0.00           O  
HETATM   14  O2  UNL     1      -4.675   1.711  -0.308  1.00  0.00           O  
HETATM   15  H1  UNL     1       5.102   0.580   0.857  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.702  -1.065   1.172  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.080  -0.581  -0.488  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.712   0.365  -1.588  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.094   2.217  -0.749  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.217   2.066   0.863  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.346   2.646  -0.574  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.105  -1.578   1.441  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.243  -0.331  -0.984  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.184   0.910   0.344  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.256  -0.535   1.692  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.249  -1.810   0.438  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.125  -0.117  -1.209  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.182   1.088   0.158  1.00  0.00           H  
HETATM   29  H15 UNL     1      -3.750  -0.279   1.390  1.00  0.00           H  
HETATM   30  H16 UNL     1      -4.833  -2.048  -0.061  1.00  0.00           H  
HETATM   31  H17 UNL     1      -3.338  -2.431   0.723  1.00  0.00           H  
HETATM   32  H18 UNL     1      -3.902   2.317  -0.574  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3
CONECT    3    4    6
CONECT    4    5   18
CONECT    5   19   20   21
CONECT    6    7   22
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

HMDB0003334
     RDKit          3D
Symmetric dimethylarginine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.9330   -0.4911    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.9474    0.9961 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830   -0.3994    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8035    0.6103   -0.5657 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522    1.9758   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -0.8141    0.7503 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436   -0.1579    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639   -0.7244    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700    0.0301   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435   -0.4592    0.2905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8024   -1.8748   -0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6359    0.3486   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4472   -0.2220   -1.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6751    1.7114   -0.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021    0.5805    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7019   -1.0651    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797   -0.5814   -0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117    0.3647   -1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    2.2168   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2171    2.0661    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455    2.6465   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1053   -1.5781    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -0.3309   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836    0.9099    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2559   -0.5345    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2488   -1.8097    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -0.1173   -1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1824    1.0877    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -0.2793    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8325   -2.0478   -0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   -2.4306    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024    2.3169   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  3  6  1  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
  4 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

Synonyms

Value	Source
(2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoic acid	ChEBI
(S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoic acid	ChEBI
Guanidino-N(1),N(2)-dimethylarginine	ChEBI
N(g1),N(g2)-Dimethylarginine	ChEBI
N,N'-dimethylarginine	ChEBI
N(3),N(4)-Dimethyl-L-arginine	ChEBI
N(3),N(4)-Dimethylarginine	ChEBI
N5-((Methylamino)(methylimino)methyl)-L-ornithine	ChEBI
N(5)-(N,N'-dimethylamidino)-L-ornithine	ChEBI
N(5)-(N,N'-dimethylcarbamimidoyl)-L-ornithine	ChEBI
N(5)-[Bis(methylamino)methylene]-L-ornithine	ChEBI
N(g),N'(g)-dimethyl-L-arginine	ChEBI
N(g),N'(g)-dimethylarginine	ChEBI
SDMA	ChEBI
(2S)-2-Amino-5-(n',n''-dimethylcarbamimidamido)pentanoate	Generator
(S)-2-Amino-5-(n',n''-dimethylguanidino)pentanoate	Generator
N5-(N,N'-dimethylamidino)-L-ornithine	HMDB
N5-[Bis(methylamino)methylene]-L-ornithine	HMDB
NG,N'G-dimethyl-L-arginine	HMDB, MeSH
NG,N'G-dimethylarginine	HMDB
NG,NG'-dimethylarginine	HMDB
Omega-N(g),n'(g)-dimethylarginine	MeSH, HMDB
SDMA arginine	MeSH, HMDB

Molecular Formula

C₈H₁₈N₄O₂

Average Mass

202.2541

Monoisotopic Mass

202.14297584

IUPAC Name

(2S)-2-amino-5-[(E)-N',N''-dimethylcarbamimidamido]pentanoic acid

Traditional Name

N3, N4-dimethylarginine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

HVPFXCBJHIIJGS-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
Carboxylic acid
Monocarboxylic acid or derivatives
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Imine
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:25682 )
non-proteinogenic L-alpha-amino acid (CHEBI:25682 )
L-arginine derivative (CHEBI:25682 )
dimethylarginine (CHEBI:25682 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.56 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-2.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	12.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.18 m³·mol⁻¹	ChemAxon
Polarizability	22.22 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

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Kidney
Placenta
Saliva
Urine

Tissue Locations

Kidney
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

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
Kidney disease	Increased	Association	Human Blood	HMDB	14500028
Uremia	Increased	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	4	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
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	2	Human ; Human supragingival plaque; Human subgingival plaque; Human feces; Human sputum; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

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 Urine	Detected and Quantified	22.0	8.0			umol/mmol creatinine	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	HMDB	18215696
Human Blood	Detected and Quantified	1.41	0.10			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	2.08	0.11			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	2.12	0.09			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	2.15	0.15			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	2.19	0.16			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	2.28	0.13			uM	Adult (>18 years old)	Not Specified	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	2.69	0.12			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	2.87	0.15			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	14500028
Human Blood	Detected and Quantified	3.170	1.0500			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	3.19	2.97			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.27	0.37			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Blood	Detected and Quantified	0.377	0.104			uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Blood	Detected and Quantified	0.38	0.10			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Blood	Detected and Quantified	0.49	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	14500028
Human Blood	Detected and Quantified	0.49		0.16	0.73	uM	Children (1-13 uears old)	Both	Normal	HMDB	27294788
Human Blood	Detected and Quantified	0.678	0.037			uM	Adult (>18 years old)	Both	Normal	HMDB	15613724
Human Blood	Detected and Quantified	1.023	0.30			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Urine	Detected and Quantified	10.90	3.86			umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	2.7		1.5	5.2	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	2.8		2.0	9.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	20.2	8.0			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18215696
Human Urine	Detected and Quantified	3.72	0.35			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	16384887
Human Urine	Detected and Quantified	4.6		3.5	7.0	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	5472370
Human Urine	Detected and Quantified			5.33	18.11	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	8.86	2.16			umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.46		0.368	0.552	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	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.
Human Blood	Detected and Quantified	0.460		0.368	0.552	uM	Adult (>18 years old)	Both	Normal	HMDB	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.
Human Saliva	Detected and Quantified	0.35	0.20			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.35	0.75	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 Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
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

External Links

HMDB ID

HMDB0003334

DrugBank ID

DB02302

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000509

KNApSAcK ID

C00052415

Chemspider ID

147942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6891

PubChem Compound

169148

PDB ID

Not Available

ChEBI ID

25682

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Boger RH, Bode-Boger SM, Szuba A, Tsao PS, Chan JR, Tangphao O, Blaschke TF, Cooke JP: Asymmetric dimethylarginine (ADMA): a novel risk factor for endothelial dysfunction: its role in hypercholesterolemia. Circulation. 1998 Nov 3;98(18):1842-7. doi: 10.1161/01.cir.98.18.1842. [PubMed:9799202 ]
Schmidt RJ, Baylis C: Total nitric oxide production is low in patients with chronic renal disease. Kidney Int. 2000 Sep;58(3):1261-6. doi: 10.1046/j.1523-1755.2000.00281.x. [PubMed:10972689 ]
Ellis J, Wennerholm UB, Bengtsson A, Lilja H, Pettersson A, Sultan B, Wennergren M, Hagberg H: Levels of dimethylarginines and cytokines in mild and severe preeclampsia. Acta Obstet Gynecol Scand. 2001 Jul;80(7):602-8. [PubMed:11437716 ]
Nijveldt RJ, Van Leeuwen PA, Van Guldener C, Stehouwer CD, Rauwerda JA, Teerlink T: Net renal extraction of asymmetrical (ADMA) and symmetrical (SDMA) dimethylarginine in fasting humans. Nephrol Dial Transplant. 2002 Nov;17(11):1999-2002. doi: 10.1093/ndt/17.11.1999. [PubMed:12401860 ]
Teerlink T, Neele SJ, de Jong S, Netelenbos JC, Stehouwer CD: Oestrogen replacement therapy lowers plasma levels of asymmetrical dimethylarginine in healthy postmenopausal women. Clin Sci (Lond). 2003 Jul;105(1):67-71. doi: 10.1042/CS20020309. [PubMed:12625833 ]
Schiel R, Franke S, Busch M, Muller A, Fleck C, Muller UA, Braun A, Stein G: Effect of smoking on risk factors for cardiovascular disease in patients with diabetes mellitus and renal insufficiency. Eur J Med Res. 2003 Jul 31;8(7):283-91. [PubMed:12911864 ]
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. doi: 10.1016/s0009-8981(03)00338-3. [PubMed:14500028 ]
Mittermayer F, Namiranian K, Pleiner J, Schaller G, Wolzt M: Acute Escherichia coli endotoxaemia decreases the plasma l-arginine/asymmetrical dimethylarginine ratio in humans. Clin Sci (Lond). 2004 Jun;106(6):577-81. doi: 10.1042/CS20030363. [PubMed:14741043 ]
Krzyzanowska K, Mittermayer F, Schnack C, Hofer M, Wolzt M, Schernthaner G: Circulating ADMA concentrations are elevated in hypopituitary adults with and without growth hormone deficiency. Eur J Clin Invest. 2005 Mar;35(3):208-13. doi: 10.1111/j.1365-2362.2005.01474.x. [PubMed:15733076 ]
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 ]
Marliss EB, Chevalier S, Gougeon R, Morais JA, Lamarche M, Adegoke OA, Wu G: Elevations of plasma methylarginines in obesity and ageing are related to insulin sensitivity and rates of protein turnover. Diabetologia. 2006 Feb;49(2):351-9. doi: 10.1007/s00125-005-0066-6. Epub 2005 Dec 21. [PubMed:16369774 ]
Mittermayer F, Pleiner J, Krzyzanowska K, Wiesinger GF, Francesconi M, Wolzt M: Regular physical exercise normalizes elevated asymmetrical dimethylarginine concentrations in patients with type 1 diabetes mellitus. Wien Klin Wochenschr. 2005 Dec;117(23-24):816-20. doi: 10.1007/s00508-005-0476-y. [PubMed:16437318 ]
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 Symmetric dimethylarginine (MMDBc0000572)

MOL for #<Metabolite:0x00007f9251c65c38>

3D MOL for #<Metabolite:0x00007f9251c65c38>

3D SDF for #<Metabolite:0x00007f9251c65c38>

3D-SDF for #<Metabolite:0x00007f9251c65c38>

PDB for #<Metabolite:0x00007f9251c65c38>

3D PDB for #<Metabolite:0x00007f9251c65c38>

SMILES for #<Metabolite:0x00007f9251c65c38>

INCHI for #<Metabolite:0x00007f9251c65c38>

Structure for #<Metabolite:0x00007f9251c65c38>

3D Structure for #<Metabolite:0x00007f9251c65c38>