MiMeDB: Showing metabocard for Spermine (MMDBc0000182)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:53 UTC

Update Date

2024-10-09 20:56:03 UTC

Metabolite ID

MMDBc0000182

Metabolite Identification

Common Name

Spermine

Description

Spermine is a biogenic polyamine formed from spermidine. It is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Spermine is found as a polycation at all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure.

Structure

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

HMDB0001256
     RDKit          3D
Spermine
 40 39  0  0  0  0  0  0  0  0999 V2000
    5.9451    0.8520    0.3288 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -0.0105   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1780   -0.7449    1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242   -1.6107    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.7655   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0411    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399    0.9997   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3466    1.8923   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    1.3441    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8915    0.4168    1.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    0.1930    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.5426   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3762   -0.7988    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997   -1.5189   -1.1620 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    1.4245    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7814    0.2866    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155   -0.7932   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473    0.6575   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841   -1.3489    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6974   -0.0456    1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -2.1743    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -2.3064   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574   -0.3354   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.5757    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8899    0.6924    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.6135   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606    0.3921   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    2.6142   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.6220    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3810    2.1972    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    0.8300   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.5601    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    1.1709    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279   -0.3448    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015   -1.5562   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.0206   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348   -1.4293    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.1586    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -0.9311   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9495   -1.9846   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
M  END

HMDB0001256
     RDKit          3D
Spermine
 40 39  0  0  0  0  0  0  0  0999 V2000
    5.9451    0.8520    0.3288 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -0.0105   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1780   -0.7449    1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242   -1.6107    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.7655   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0411    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399    0.9997   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3466    1.8923   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    1.3441    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8915    0.4168    1.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    0.1930    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.5426   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3762   -0.7988    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997   -1.5189   -1.1620 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    1.4245    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7814    0.2866    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155   -0.7932   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473    0.6575   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841   -1.3489    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6974   -0.0456    1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -2.1743    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -2.3064   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574   -0.3354   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.5757    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8899    0.6924    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.6135   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606    0.3921   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    2.6142   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.6220    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3810    2.1972    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    0.8300   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.5601    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    1.1709    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279   -0.3448    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015   -1.5562   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.0206   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348   -1.4293    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.1586    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -0.9311   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9495   -1.9846   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 127                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0       9.241   0.385   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      15.909  -0.385   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.907   0.385   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      21.243  -0.385   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      11.908   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.242  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.575  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.575   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.907  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.243   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.576  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.240  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.909   0.385   0.000  0.00  0.00           C+0
CONECT    1    7    9                                                       
CONECT    2    8   10                                                       
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    1    5                                                       
CONECT    8    2    6                                                       
CONECT    9    1   11                                                       
CONECT   10    2   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13    3   11                                                       
CONECT   14    4   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0001256
HETATM    1  N1  UNL     1       5.945   0.852   0.329  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.890  -0.010  -0.134  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.178  -0.745   1.003  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.124  -1.611   0.272  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.272  -0.766  -0.446  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.324   0.041   0.259  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.740   1.000  -0.728  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.347   1.892  -0.308  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.670   1.344   0.009  1.00  0.00           C  
HETATM   10  N3  UNL     1      -1.892   0.417   1.034  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.368   0.193   1.112  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.876  -0.543  -0.081  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.376  -0.799   0.026  1.00  0.00           C  
HETATM   14  N4  UNL     1      -5.800  -1.519  -1.162  1.00  0.00           N  
HETATM   15  H1  UNL     1       5.587   1.425   1.114  1.00  0.00           H  
HETATM   16  H2  UNL     1       6.781   0.287   0.567  1.00  0.00           H  
HETATM   17  H3  UNL     1       5.216  -0.793  -0.848  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.147   0.657  -0.639  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.884  -1.349   1.571  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.697  -0.046   1.698  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.550  -2.174   1.039  1.00  0.00           H  
HETATM   22  H8  UNL     1       3.647  -2.306  -0.413  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.557  -0.335  -1.312  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.591  -0.576   0.750  1.00  0.00           H  
HETATM   25  H11 UNL     1       1.890   0.692   1.002  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.650   1.614  -1.082  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.461   0.392  -1.653  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.520   2.614  -1.186  1.00  0.00           H  
HETATM   29  H15 UNL     1       0.020   2.622   0.487  1.00  0.00           H  
HETATM   30  H16 UNL     1      -2.381   2.197   0.179  1.00  0.00           H  
HETATM   31  H17 UNL     1      -2.006   0.830  -0.969  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.505  -0.560   0.809  1.00  0.00           H  
HETATM   33  H19 UNL     1      -3.887   1.171   1.157  1.00  0.00           H  
HETATM   34  H20 UNL     1      -3.628  -0.345   2.032  1.00  0.00           H  
HETATM   35  H21 UNL     1      -3.402  -1.556  -0.100  1.00  0.00           H  
HETATM   36  H22 UNL     1      -3.727  -0.021  -1.050  1.00  0.00           H  
HETATM   37  H23 UNL     1      -5.635  -1.429   0.899  1.00  0.00           H  
HETATM   38  H24 UNL     1      -5.932   0.159   0.127  1.00  0.00           H  
HETATM   39  H25 UNL     1      -6.253  -0.931  -1.875  1.00  0.00           H  
HETATM   40  H26 UNL     1      -4.949  -1.985  -1.573  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23
CONECT    6    7   24   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   39   40
END

HMDB0001256
     RDKit          3D
Spermine
 40 39  0  0  0  0  0  0  0  0999 V2000
    5.9451    0.8520    0.3288 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900   -0.0105   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1780   -0.7449    1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1242   -1.6107    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.7655   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.0411    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399    0.9997   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3466    1.8923   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    1.3441    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8915    0.4168    1.0337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    0.1930    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.5426   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3762   -0.7988    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7997   -1.5189   -1.1620 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5867    1.4245    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7814    0.2866    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155   -0.7932   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473    0.6575   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8841   -1.3489    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6974   -0.0456    1.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -2.1743    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -2.3064   -0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574   -0.3354   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.5757    0.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8899    0.6924    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.6135   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606    0.3921   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    2.6142   -1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.6220    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3810    2.1972    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    0.8300   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -0.5601    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8867    1.1709    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6279   -0.3448    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4015   -1.5562   -0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -0.0206   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348   -1.4293    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.1586    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -0.9311   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9495   -1.9846   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
M  END

Synonyms

Value	Source
4,9-Diaza-1,12-dodecanediamine	ChEBI
4,9-Diazadodecane-1,12-diamine	ChEBI
N,N'-bis(3-aminopropyl)-1,4-butanediamine	ChEBI
1,5,10,14-Tetraazatetradecane	HMDB
4,9-Diazadodecamethylenediamine	HMDB
Diaminopropyl-tetramethylenediamine	HMDB
Diaminopropyltetramethylenediamine	HMDB
Gerontine	HMDB
Musculamine	HMDB
N,N'-bis(3-aminopropyl)-1,4-tetramethylenediamine	HMDB
N,N'-bis(3-aminopropyl)butane-1,4-diamine	HMDB
N1,N4-Bis(3-aminopropyl)-1,4-butanediamine	HMDB
Neuridine	HMDB
Spermin	HMDB
Spermine dihydrate	HMDB
Spermine puriss	HMDB
SPM	HMDB

Molecular Formula

C₁₀H₂₆N₄

Average Mass

202.3402

Monoisotopic Mass

202.215746852

IUPAC Name

(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine

Traditional Name

spermine

CAS Registry Number

71-44-3

SMILES

NCCCNCCCCNCCCN

InChI Identifier

InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2

InChI Key

PFNFFQXMRSDOHW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylamines

Alternative Parents

Substituents

Secondary aliphatic amine
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetraamine (CHEBI:15746 )
polyazaalkane (CHEBI:15746 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.19 g/L	ALOGPS
logP	-0.66	ALOGPS
logP	-1.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	10.8	ChemAxon
Physiological Charge	4	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	76.1 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	62.56 m³·mol⁻¹	ChemAxon
Polarizability	26.69 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Epidermis
Erythrocyte
Feces
Fibroblasts
Intestine
Liver
Neuron
Pancreas
Platelet
Prostate
Saliva
Skeletal Muscle
Testis
Urine

Tissue Locations

Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Liver
Neuron
Pancreas
Platelet
Prostate
Skeletal Muscle
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191691	Diamine acetyltransferase 2	Enzyme	Q96F10	Homo sapiens
MMDBp0191705	Diamine acetyltransferase 1	Enzyme	P21673	Homo sapiens
MMDBp0191852	Xanthine dehydrogenase/oxidase	Unknown	P47989	Homo sapiens
MMDBp0191872	Choline dehydrogenase, mitochondrial	Unknown	Q8NE62	Homo sapiens
MMDBp0191874	Dimethylglycine dehydrogenase, mitochondrial	Unknown	Q9UI17	Homo sapiens
MMDBp0191887	Spermine synthase	Enzyme	P52788	Homo sapiens
MMDBp0191888	Spermidine synthase	Enzyme	P19623	Homo sapiens
MMDBp0191961	4-trimethylaminobutyraldehyde dehydrogenase	Unknown	P49189	Homo sapiens
MMDBp0192049	Gamma-butyrobetaine dioxygenase	Unknown	O75936	Homo sapiens
MMDBp0192057	Amiloride-sensitive amine oxidase [copper-containing]	Unknown	P19801	Homo sapiens
MMDBp0192064	S-methyl-5'-thioadenosine phosphorylase	Enzyme	Q13126	Homo sapiens
MMDBp0192086	S-adenosylmethionine decarboxylase proenzyme	Unknown	P17707	Homo sapiens
MMDBp0192122	Glycine amidinotransferase, mitochondrial	Enzyme	P50440	Homo sapiens
MMDBp0192205	Betaine--homocysteine S-methyltransferase 1	Unknown	Q93088	Homo sapiens
MMDBp0192413	Sarcosine dehydrogenase, mitochondrial	Unknown	Q9UL12	Homo sapiens
MMDBp0192503	Histidine decarboxylase	Enzyme	P19113	Homo sapiens
MMDBp0192645	Ornithine decarboxylase	Enzyme	P11926	Homo sapiens
MMDBp0193543	Solute carrier family 22 member 4	Transporter	Q9H015	Homo sapiens
MMDBp0193588	Solute carrier family 22 member 1	Transporter	O15245	Homo sapiens
MMDBp0193618	Spermine oxidase	Unknown	Q9NWM0	Homo sapiens
MMDBp0193643	Agmatinase, mitochondrial	Unknown	Q9BSE5	Homo sapiens
MMDBp0193925	Trimethyllysine dioxygenase, mitochondrial	Unknown	Q9NVH6	Homo sapiens
MMDBp0193964	S-methylmethionine--homocysteine S-methyltransferase BHMT2	Unknown	Q9H2M3	Homo sapiens
MMDBp0195554	Pyruvate dehydrogenase phosphatase regulatory subunit, mitochondrial	Unknown	Q8NCN5	Homo sapiens
MMDBp0196292	Ornithine decarboxylase antizyme 1	Enzyme	P54368	Homo sapiens
MMDBp0196552	Polyamine-modulated factor 1	Unknown	Q6P1K2	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019423	Spermine	Spermidine	Polyamine oxidase FMS1	Oxidation	PathBank	31602464
MMDBr0019428	Spermidine	Spermine	Spermine synthase SPE4	Synthesis	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Leukemia	Increased	Association	Human Urine	HMDB	9464484
Uremia	Decreased	Association	Human Blood	HMDB	22626821
Uremia		Association	Human Blood	HMDB	12675874

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	3	Human feces	Microbial culture
Bacteria/Eubacteria	Proteobacteria	5	Human ; Human feces	Microbial culture
Bacteria/Eubacteria	Actinobacteria	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	2	Human ; Human feces	Microbial culture
Bacteria/Eubacteria	Deinococcus-thermus	1
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

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

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.463	0.214			umol/mmol creatinine	Adult (>18 years old)	Both	Leukemia	HMDB	9464484
Human Blood	Detected and Quantified	0.0092	0.0076			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	0.0901	0.0802			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Urine	Detected and Quantified	0.019				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Saliva	Detected and Quantified	0.04				uM	Adult (>18 years old)	Both	Normal	HMDB	11419735
Human Urine	Detected and Quantified			0.01	0.62	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.03	0.04			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Urine	Detected and Quantified	0.03		0.01	0.28	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.058	0.026			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9464484
Human Urine	Detected and Quantified	0.06		0.01	0.72	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.08		0.01	0.28	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	3757213
Human Blood	Detected and Quantified	0.09		0.06	0.14	uM	Children (1-13 uears old)	Both	Normal	HMDB	27294788
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.14	0.01			uM	Adult (>18 years old)	Both	Normal	HMDB	15745737
Human Blood	Detected and Quantified			0.15	0.50	uM	Adult (>18 years old)	Both	Normal	HMDB	6588257
Human Urine	Detected and Quantified	0.13	0.065			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	9.97	3.26			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.00733	0.0381			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.0665	0.0665			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.0962	0.262			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.242	0.565			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.63	0.67			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9464484
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	22727327
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001256

DrugBank ID

DB00127

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15746

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Proctor MS, Fletcher HV Jr, Shukla JB, Rennert OM: Elevated spermidine and spermine levels in the blood of psoriasis patients. J Invest Dermatol. 1975 Oct;65(4):409-11. doi: 10.1111/1523-1747.ep12607659. [PubMed:1176793 ]
Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer. Cancer. 1990 Feb 15;65(4):958-66. doi: 10.1002/1097-0142(19900215)65:4<958::aid-cncr2820650423>3.0.co;2-z. [PubMed:2297664 ]
Swift TA, Dias JA: Effects of the polyamine spermine on binding of follicle-stimulating hormone to membrane-bound immature bovine testis receptors. Biochim Biophys Acta. 1986 Feb 21;885(2):221-30. doi: 10.1016/0167-4889(86)90092-3. [PubMed:3004602 ]
El Baze P, Milano G, Verrando P, Renee N, Ortonne JP: Polyamine levels in normal human skin. A comparative study of pure epidermis, pure dermis, and suction blister fluid. Arch Dermatol Res. 1983;275(4):218-21. doi: 10.1007/BF00416663. [PubMed:6625645 ]
Jensen PK, Therkelsen AJ: Selective inhibition of fibroblasts by spermine in primary cultures of normal human skin epithelial cells. In Vitro. 1982 Oct;18(10):867-71. doi: 10.1007/BF02796328. [PubMed:7173947 ]
Uehara N, Shirakawa S, Uchino H, Saeki Y: Elevated contents of spermidine and spermine in the erythrocytes of cancer patients. Cancer. 1980 Jan 1;45(1):108-11. doi: 10.1002/1097-0142(19800101)45:1<108::aid-cncr2820450120>3.0.co;2-w. [PubMed:7350997 ]
Mollica F, Li Volti S, Rapisarda A, Longo G, Pavone L, Vanella A: Increased erythrocytic spermine in Duchenne muscular dystrophy. Pediatr Res. 1980 Nov;14(11):1196-8. doi: 10.1203/00006450-198011000-00009. [PubMed:7454431 ]
Cipolla BG, Ziade J, Bansard JY, Moulinoux JP, Staerman F, Quemener V, Lobel B, Guille F: Pretherapeutic erythrocyte polyamine spermine levels discriminate high risk relapsing patients with M1 prostate carcinoma. Cancer. 1996 Sep 1;78(5):1055-65. doi: 10.1002/(SICI)1097-0142(19960901)78:5<1055::AID-CNCR16>3.0.CO;2-1. [PubMed:8780544 ]
Lorenz B, Francis F, Gempel K, Boddrich A, Josten M, Schmahl W, Schmidt J, Lehrach H, Meitinger T, Strom TM: Spermine deficiency in Gy mice caused by deletion of the spermine synthase gene. Hum Mol Genet. 1998 Mar;7(3):541-7. doi: 10.1093/hmg/7.3.541. [PubMed:9467015 ]
Venza M, Visalli M, Cicciu D, Teti D: Determination of polyamines in human saliva by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):111-7. doi: 10.1016/s0378-4347(01)00130-x. [PubMed:11419735 ]
Hosseinkhani H, Azzam T, Tabata Y, Domb AJ: Dextran-spermine polycation: an efficient nonviral vector for in vitro and in vivo gene transfection. Gene Ther. 2004 Jan;11(2):194-203. doi: 10.1038/sj.gt.3302159. [PubMed:14712304 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 ]

Showing metabocard for Spermine (MMDBc0000182)

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3D Structure for #<Metabolite:0x00005645c9c120b8>