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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-10 09:50:09 UTC

Update Date

2023-02-21 17:16:36 UTC

HMDB ID

HMDB0003334

Secondary Accession Numbers

HMDB03334

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>
HMDB0003334

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₈H₁₈N₄O₂

Average Molecular Weight

202.2541

Monoisotopic Molecular Weight

202.14297584

IUPAC Name

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

Traditional Name

N3, N4-dimethylarginine

CAS Registry Number

30344-00-4

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 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0003334)

Bleeding (HMDB: HMDB0003334)
Weight loss (HMDB: HMDB0003334)

Digestive system disorder

Gastrointestinal disorder

Nausea (HMDB: HMDB0003334)
Vomiting (HMDB: HMDB0003334)

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Renal system and urinary system

Renal disorder

Chronic kidney disease (HMDB: HMDB0003334)
Uremia (HMDB: HMDB0003334)
Kidney disease (HMDB: HMDB0003334)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0003334)

Organ

Kidney (HMDB: HMDB0003334)
Placenta (HMDB: HMDB0003334)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0003334)
Saliva (HMDB: HMDB0003334)
Cerebrospinal Fluid (CSF) (PMID: 31726035)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0003334)
Urine (HMDB: HMDB0003334)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0003334)

Enteral

Ingestion (HMDB: HMDB0003334)

Source

Endogenous

Endogenous (HMDB: HMDB0003334)

Plant

Fabaceae (HMDB: HMDB0003334)

Exogenous

Food

Food (HMDB: HMDB0003334)

Animal origin

Poultry

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Pulse

Pulses (FooDB: FOOD00867)

Not Available

EC 1.14.13.39 (nitric oxide synthase) inhibitor (HMDB: HMDB0003334)

Waste product (PMID: 35448883)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003334)

Biomarker

Kidney disease (MarkerDB: MDB00013448)
Chronic kidney disease (MarkerDB: MDB00013448)
Uremia (MarkerDB: MDB00013448)
Autosomal dominant polycystic kidney disease (MarkerDB: MDB00013448)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.161	31661259
DarkChem	[M-H]-	145.961	31661259
DeepCCS	[M+H]+	149.375	30932474
DeepCCS	[M-H]-	147.017	30932474
DeepCCS	[M-2H]-	181.008	30932474
DeepCCS	[M+Na]+	155.593	30932474
AllCCS	[M+H]+	147.2	32859911
AllCCS	[M+H-H2O]+	143.7	32859911
AllCCS	[M+NH4]+	150.6	32859911
AllCCS	[M+Na]+	151.5	32859911
AllCCS	[M-H]-	146.5	32859911
AllCCS	[M+Na-2H]-	147.8	32859911
AllCCS	[M+HCOO]-	149.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Symmetric dimethylarginine	CN\C(NCCC[C@H](N)C(O)=O)=N/C	2803.6	Standard polar	33892256
Symmetric dimethylarginine	CN\C(NCCC[C@H](N)C(O)=O)=N/C	2155.0	Standard non polar	33892256
Symmetric dimethylarginine	CN\C(NCCC[C@H](N)C(O)=O)=N/C	2285.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Symmetric dimethylarginine,1TMS,isomer #1	C/N=C(\NC)NCCC[C@H](N)C(=O)O[Si](C)(C)C	1990.9	Semi standard non polar	33892256
Symmetric dimethylarginine,1TMS,isomer #2	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C)C(=O)O	2094.1	Semi standard non polar	33892256
Symmetric dimethylarginine,1TMS,isomer #3	C/N=C(/NCCC[C@H](N)C(=O)O)N(C)[Si](C)(C)C	2077.3	Semi standard non polar	33892256
Symmetric dimethylarginine,1TMS,isomer #4	C/N=C(\NC)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	2084.6	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #1	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2062.8	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #1	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1811.0	Standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #1	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	3534.3	Standard polar	33892256
Symmetric dimethylarginine,2TMS,isomer #2	C/N=C(/NCCC[C@H](N)C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	2049.4	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #2	C/N=C(/NCCC[C@H](N)C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	1802.1	Standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #2	C/N=C(/NCCC[C@H](N)C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	3390.1	Standard polar	33892256
Symmetric dimethylarginine,2TMS,isomer #3	C/N=C(\NC)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2011.1	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #3	C/N=C(\NC)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1835.2	Standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #3	C/N=C(\NC)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3423.7	Standard polar	33892256
Symmetric dimethylarginine,2TMS,isomer #4	C/N=C(/NCCC[C@H](N[Si](C)(C)C)C(=O)O)N(C)[Si](C)(C)C	2117.9	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #4	C/N=C(/NCCC[C@H](N[Si](C)(C)C)C(=O)O)N(C)[Si](C)(C)C	1804.9	Standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #4	C/N=C(/NCCC[C@H](N[Si](C)(C)C)C(=O)O)N(C)[Si](C)(C)C	3302.7	Standard polar	33892256
Symmetric dimethylarginine,2TMS,isomer #5	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2104.2	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #5	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1824.1	Standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #5	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3366.2	Standard polar	33892256
Symmetric dimethylarginine,2TMS,isomer #6	C/N=C(\NC)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2188.7	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #6	C/N=C(\NC)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1887.9	Standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #6	C/N=C(\NC)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3621.9	Standard polar	33892256
Symmetric dimethylarginine,2TMS,isomer #7	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	2074.4	Semi standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #7	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	1944.4	Standard non polar	33892256
Symmetric dimethylarginine,2TMS,isomer #7	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	3473.6	Standard polar	33892256
Symmetric dimethylarginine,3TMS,isomer #1	C/N=C(/NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	2108.5	Semi standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #1	C/N=C(/NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	1822.3	Standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #1	C/N=C(/NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N(C)[Si](C)(C)C	2932.7	Standard polar	33892256
Symmetric dimethylarginine,3TMS,isomer #2	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2070.0	Semi standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #2	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1841.1	Standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #2	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2964.6	Standard polar	33892256
Symmetric dimethylarginine,3TMS,isomer #3	C/N=C(\NC)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2186.4	Semi standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #3	C/N=C(\NC)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1939.8	Standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #3	C/N=C(\NC)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3287.0	Standard polar	33892256
Symmetric dimethylarginine,3TMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2044.2	Semi standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1992.7	Standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2987.1	Standard polar	33892256
Symmetric dimethylarginine,3TMS,isomer #5	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2126.7	Semi standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #5	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2008.7	Standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #5	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2828.4	Standard polar	33892256
Symmetric dimethylarginine,3TMS,isomer #6	C/N=C(/NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N(C)[Si](C)(C)C	2225.7	Semi standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #6	C/N=C(/NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N(C)[Si](C)(C)C	1924.2	Standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #6	C/N=C(/NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N(C)[Si](C)(C)C	3046.9	Standard polar	33892256
Symmetric dimethylarginine,3TMS,isomer #7	C/N=C(\NC)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2184.3	Semi standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #7	C/N=C(\NC)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1943.6	Standard non polar	33892256
Symmetric dimethylarginine,3TMS,isomer #7	C/N=C(\NC)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3083.9	Standard polar	33892256
Symmetric dimethylarginine,4TMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2122.1	Semi standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2018.8	Standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2480.0	Standard polar	33892256
Symmetric dimethylarginine,4TMS,isomer #2	C/N=C(/NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N(C)[Si](C)(C)C	2236.0	Semi standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #2	C/N=C(/NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N(C)[Si](C)(C)C	1932.4	Standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #2	C/N=C(/NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N(C)[Si](C)(C)C	2766.0	Standard polar	33892256
Symmetric dimethylarginine,4TMS,isomer #3	C/N=C(\NC)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2197.6	Semi standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #3	C/N=C(\NC)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1959.7	Standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #3	C/N=C(\NC)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2785.6	Standard polar	33892256
Symmetric dimethylarginine,4TMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2237.7	Semi standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2132.2	Standard non polar	33892256
Symmetric dimethylarginine,4TMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2616.1	Standard polar	33892256
Symmetric dimethylarginine,5TMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2288.2	Semi standard non polar	33892256
Symmetric dimethylarginine,5TMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2126.7	Standard non polar	33892256
Symmetric dimethylarginine,5TMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2374.4	Standard polar	33892256
Symmetric dimethylarginine,1TBDMS,isomer #1	C/N=C(\NC)NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2223.2	Semi standard non polar	33892256
Symmetric dimethylarginine,1TBDMS,isomer #2	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2309.5	Semi standard non polar	33892256
Symmetric dimethylarginine,1TBDMS,isomer #3	C/N=C(/NCCC[C@H](N)C(=O)O)N(C)[Si](C)(C)C(C)(C)C	2292.0	Semi standard non polar	33892256
Symmetric dimethylarginine,1TBDMS,isomer #4	C/N=C(\NC)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2286.8	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #1	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2494.2	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #1	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2216.3	Standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #1	C/N=C(\NC)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3467.1	Standard polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #2	C/N=C(/NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2458.6	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #2	C/N=C(/NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2232.0	Standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #2	C/N=C(/NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	3351.6	Standard polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #3	C/N=C(\NC)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2430.1	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #3	C/N=C(\NC)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2230.9	Standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #3	C/N=C(\NC)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3366.3	Standard polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #4	C/N=C(/NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N(C)[Si](C)(C)C(C)(C)C	2551.3	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #4	C/N=C(/NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N(C)[Si](C)(C)C(C)(C)C	2230.4	Standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #4	C/N=C(/NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)N(C)[Si](C)(C)C(C)(C)C	3248.3	Standard polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #5	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2526.5	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #5	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2210.1	Standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #5	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3276.0	Standard polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #6	C/N=C(\NC)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2604.8	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #6	C/N=C(\NC)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2289.8	Standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #6	C/N=C(\NC)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3554.9	Standard polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #7	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2499.3	Semi standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #7	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2349.9	Standard non polar	33892256
Symmetric dimethylarginine,2TBDMS,isomer #7	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	3353.5	Standard polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #1	C/N=C(/NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2725.1	Semi standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #1	C/N=C(/NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2410.8	Standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #1	C/N=C(/NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	3020.5	Standard polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #2	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2698.0	Semi standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #2	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2394.1	Standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #2	C/N=C(\NC)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3031.6	Standard polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #3	C/N=C(\NC)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2800.4	Semi standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #3	C/N=C(\NC)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2530.0	Standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #3	C/N=C(\NC)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3295.5	Standard polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2670.4	Semi standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2556.4	Standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3061.8	Standard polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #5	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2752.9	Semi standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #5	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2566.3	Standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #5	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2941.6	Standard polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #6	C/N=C(/NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2863.6	Semi standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #6	C/N=C(/NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2527.7	Standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #6	C/N=C(/NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	3088.3	Standard polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #7	C/N=C(\NC)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2837.4	Semi standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #7	C/N=C(\NC)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2510.6	Standard non polar	33892256
Symmetric dimethylarginine,3TBDMS,isomer #7	C/N=C(\NC)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3103.0	Standard polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2918.4	Semi standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2722.3	Standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2823.0	Standard polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #2	C/N=C(/NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	3065.5	Semi standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #2	C/N=C(/NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2687.2	Standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #2	C/N=C(/NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C)[Si](C)(C)C(C)(C)C	2979.8	Standard polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #3	C/N=C(\NC)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3054.0	Semi standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #3	C/N=C(\NC)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2676.4	Standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #3	C/N=C(\NC)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2989.3	Standard polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3057.4	Semi standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2824.7	Standard non polar	33892256
Symmetric dimethylarginine,4TBDMS,isomer #4	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2880.2	Standard polar	33892256
Symmetric dimethylarginine,5TBDMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3281.8	Semi standard non polar	33892256
Symmetric dimethylarginine,5TBDMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2990.8	Standard non polar	33892256
Symmetric dimethylarginine,5TBDMS,isomer #1	C/N=C(\N(C)[Si](C)(C)C(C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2805.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Symmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kfx-9600000000-f6c986d30ea287579a78	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Symmetric dimethylarginine GC-MS (1 TMS) - 70eV, Positive	splash10-0fkc-9720000000-0f297fd1183458956770	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Symmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Symmetric dimethylarginine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Symmetric dimethylarginine 35V, Positive-QTOF	splash10-00di-9600000000-a9cb6507d9fe3ffb39aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Symmetric dimethylarginine 10V, Negative-QTOF	splash10-053r-3910000000-1a8526e47c9af75d4cc9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Symmetric dimethylarginine 20V, Negative-QTOF	splash10-0a59-9400000000-777d41b210dd091439b4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 10V, Positive-QTOF	splash10-0pbi-1930000000-98ffa2f50a3e5ee90e10	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 20V, Positive-QTOF	splash10-0abi-8900000000-eccaa3c6c71a7aab8dd3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 40V, Positive-QTOF	splash10-00di-9000000000-fd3f3045e508262e68be	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 10V, Negative-QTOF	splash10-0udi-3390000000-ec3717ed507fec531202	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 20V, Negative-QTOF	splash10-000i-9520000000-06ed24b7ccb74ccd705b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 40V, Negative-QTOF	splash10-00dr-9000000000-40bdb35b370bc3317a55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 10V, Positive-QTOF	splash10-0udi-2190000000-1ff257e4be06b9702e65	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 20V, Positive-QTOF	splash10-00di-9100000000-b9dfe8a8d6f891dcecbf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 40V, Positive-QTOF	splash10-00di-9000000000-926c9fc48c09f4030499	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 10V, Negative-QTOF	splash10-0ue9-1590000000-567e7d20ebbf052f8d39	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 20V, Negative-QTOF	splash10-001i-2900000000-84e3189b175eab73e2c5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Symmetric dimethylarginine 40V, Negative-QTOF	splash10-0a4i-9000000000-c8ec00d7abbc06aa7e4c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Kidney
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.35-0.75 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.460 (0.368-0.552) uM	Adult (>18 years old)	Both	Normal	Martens-Lobenhoff...	details
Blood	Detected and Quantified	1.023 +/- 0.30 uM	Adult (>18 years old)	Both	Normal	31726035	details
Blood	Detected and Quantified	0.49 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	14500028	details
Blood	Detected and Quantified	0.678 +/- 0.037 uM	Adult (>18 years old)	Both	Normal	15613724	details
Blood	Detected and Quantified	0.38 +/- 0.10 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected and Quantified	0.46 (0.368-0.552) uM	Adult (>18 years old)	Not Specified	Normal	Martens-Lobenhoff...	details
Blood	Detected and Quantified	0.49(0.16-0.73) uM	Children (1-13 uears old)	Both	Normal	27294788	details
Blood	Detected and Quantified	0.377 +/- 0.104 uM	Adult (>18 years old)	Both	Normal	12675874	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.27 +/- 0.37 uM	Adult (>18 years old)	Both	Normal	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	0.35 +/- 0.20 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	3.72 +/- 0.35 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	16384887	details
Urine	Detected and Quantified	4.6 (3.5-7.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	5472370	details
Urine	Detected and Quantified	5.33-18.11 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	10.90 +/- 3.86 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	8.86 +/- 2.16 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	20.2 +/- 8.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	18215696	details
Urine	Detected and Quantified	2.8 (2.0-9.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.7 (1.5-5.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.073 +/- 0.23 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Blood	Detected and Quantified	2.08 +/- 0.11 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	1.13 +/- 0.44 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Blood	Detected and Quantified	1.068 +/- 0.14 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Blood	Detected and Quantified	3.19 +/- 2.97 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected and Quantified	2.69 +/- 0.12 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	2.28 +/- 0.13 uM	Adult (>18 years old)	Not Specified	Kidney disease	14500028	details
Blood	Detected and Quantified	1.41 +/- 0.10 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	2.19 +/- 0.16 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	2.87 +/- 0.15 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	0.42(0.09-0.70) uM	Children (1-13 uears old)	Both	Environmental enteric dysfunction	27294788	details
Blood	Detected and Quantified	2.15 +/- 0.15 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	2.12 +/- 0.09 uM	Adult (>18 years old)	Both	Kidney disease	14500028	details
Blood	Detected and Quantified	3.170 +/- 1.0500 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.37 +/- 0.25 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.47 +/- 0.28 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.26 +/- 0.13 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Urine	Detected and Quantified	22.0 +/- 8.0 umol/mmol creatinine	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	18215696	details

Associated Disorders and Diseases

Disease References

Kidney disease
Fleck C, Schweitzer F, Karge E, Busch M, Stein G: Serum concentrations of asymmetric (ADMA) and symmetric (SDMA) dimethylarginine in patients with chronic kidney diseases. Clin Chim Acta. 2003 Oct;336(1-2):1-12. [PubMed:14500028 ]
Uremia
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ] Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Autosomal dominant polycystic kidney disease
Wang D, Strandgaard S, Borresen ML, Luo Z, Connors SG, Yan Q, Wilcox CS: Asymmetric dimethylarginine and lipid peroxidation products in early autosomal dominant polycystic kidney disease. Am J Kidney Dis. 2008 Feb;51(2):184-91. doi: 10.1053/j.ajkd.2007.09.020. [PubMed:18215696 ]

Associated OMIM IDs

266600 (Crohn's disease)
114500 (Colorectal cancer)
601313 (Autosomal dominant polycystic kidney disease)

External Links

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

VMH ID

Not Available

MarkerDB ID

MDB00013448

Good Scents ID

Not Available

References

Synthesis Reference

Zinellu Angelo; Sotgia Salvatore; Scanu Bastianina; Formato Marilena; Deiana Luca; Carru Ciriaco Assessment of protein-incorporated arginine methylation in biological specimens by CZE UV-detection. Electrophoresis (2007), 28(23), 4452-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Martens-Lobenhoffer J, Bode-Boger SM: Measurement of asymmetric dimethylarginine (ADMA) in human plasma: from liquid chromatography estimation to liquid chromatography-mass spectrometry quantification. Eur J Clin Pharmacol. 2006 Feb;62(Supplement 13):61-68. [PubMed:16217682 ]
Wang J, Sim AS, Wang XL, Salonikas C, Naidoo D, Wilcken DE: Relations between plasma asymmetric dimethylarginine (ADMA) and risk factors for coronary disease. Atherosclerosis. 2006 Feb;184(2):383-8. Epub 2005 Jun 6. [PubMed:15939423 ]
Fleck C, Schweitzer F, Karge E, Busch M, Stein G: Serum concentrations of asymmetric (ADMA) and symmetric (SDMA) dimethylarginine in patients with chronic kidney diseases. Clin Chim Acta. 2003 Oct;336(1-2):1-12. [PubMed:14500028 ]
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. [PubMed:9799202 ]
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. [PubMed:12401860 ]
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 ]
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. [PubMed:16437318 ]
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. [PubMed:15733076 ]
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. Epub 2005 Dec 21. [PubMed:16369774 ]
Schmidt RJ, Baylis C: Total nitric oxide production is low in patients with chronic renal disease. Kidney Int. 2000 Sep;58(3):1261-6. [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 ]
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. [PubMed:12625833 ]
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. [PubMed:14741043 ]
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 ]

Showing metabocard for Symmetric dimethylarginine (HMDB0003334)

MOL for HMDB0003334 (Symmetric dimethylarginine)

3D MOL for HMDB0003334 (Symmetric dimethylarginine)

3D SDF for HMDB0003334 (Symmetric dimethylarginine)

3D-SDF for HMDB0003334 (Symmetric dimethylarginine)

PDB for HMDB0003334 (Symmetric dimethylarginine)

3D PDB for HMDB0003334 (Symmetric dimethylarginine)

SMILES for HMDB0003334 (Symmetric dimethylarginine)

INCHI for HMDB0003334 (Symmetric dimethylarginine)

Structure for HMDB0003334 (Symmetric dimethylarginine)

3D Structure for HMDB0003334 (Symmetric dimethylarginine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra