NP-MRD: Showing NP-Card for Symmetric dimethylarginine (NP0000724)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2006-08-10 09:50:09 UTC

Updated at

2021-06-29 00:47:44 UTC

NP-MRD ID

NP0000724

Secondary Accession Numbers

None

Natural Product 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>
NP0000724

> <DATABASE_NAME>
NP-MRD

> <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

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
NG,N'G-dimethylarginine	HMDB
NG,NG'-dimethylarginine	HMDB
Omega-N(g),n'(g)-dimethylarginine	HMDB
SDMA arginine	HMDB

Chemical Formula

C₈H₁₈N₄O₂

Average Mass

202.2541 Da

Monoisotopic Mass

202.14298 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental 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

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

External Links

HMDB ID

HMDB0003334

DrugBank ID

DB02302

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Symmetric dimethylarginine (NP0000724)

MOL for NP0000724 (Symmetric dimethylarginine)

3D MOL for NP0000724 (Symmetric dimethylarginine)

3D SDF for NP0000724 (Symmetric dimethylarginine)

3D-SDF for NP0000724 (Symmetric dimethylarginine)

PDB for NP0000724 (Symmetric dimethylarginine)

3D PDB for NP0000724 (Symmetric dimethylarginine)

SMILES for NP0000724 (Symmetric dimethylarginine)

INCHI for NP0000724 (Symmetric dimethylarginine)

Structure for NP0000724 (Symmetric dimethylarginine)

3D Structure for NP0000724 (Symmetric dimethylarginine)