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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:14 UTC

HMDB ID

HMDB0014631

Secondary Accession Numbers

HMDB14631

Metabolite Identification

Common Name

Altretamine

Description

Altretamine is only found in individuals that have used or taken this drug. It is an alkylating agent proposed as an antineoplastic. It also acts as a chemosterilant for male houseflies and other insects. [PubChem]The precise mechanism by which altretamine exerts its cytotoxic effect is unknown although it is classified as an alkylating anti-neoplastic agent. Through this mechanism, the drug is metabolized into alkylating agents by N-demethylation. These alkylating species consequently damage tumor cells.

Structure

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

HMDB0014631
     RDKit          3D
Altretamine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -1.7631   -3.2830   -0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098   -2.4121    0.3640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111   -2.7618    1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -1.1740    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.0173   -0.0646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    1.1550   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716    2.3077   -0.4611 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    3.2072    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0580    2.5563   -1.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883    1.2194   -0.2580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.0751   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.0742    0.0076 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473    0.2570    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232   -0.1051   -1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.0879    0.1586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -2.7719   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467   -3.5612   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267   -4.2619   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249   -3.6501    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -1.8436    2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771   -2.8482    2.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5820    3.8423    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    3.9122    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7559    2.6658    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1181    3.6696   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017    2.1264   -1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826    2.1214   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109    0.0520    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483   -0.3880    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    1.3376    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5819   -0.4127   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -0.8861   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    0.8856   -1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  2  0
 15  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END

488
  Mrv0541 02231214432D          

 15 15  0  0  0  0            999 V2000
    3.7934    1.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2  8  1  0  0  0  0
  2 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3  9  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014631

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C9H18N6/c1-13(2)7-10-8(14(3)4)12-9(11-7)15(5)6/h1-6H3

> <INCHI_KEY>
UUVWYPNAQBNQJQ-UHFFFAOYSA-N

> <FORMULA>
C9H18N6

> <MOLECULAR_WEIGHT>
210.2794

> <EXACT_MASS>
210.159294606

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
23.69518862383099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N2,N2,N4,N4,N6,N6-hexamethyl-1,3,5-triazine-2,4,6-triamine

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.2162216589999995

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.750111917945035

> <JCHEM_POLAR_SURFACE_AREA>
48.39

> <JCHEM_REFRACTIVITY>
65.6454

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
altretamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014631
     RDKit          3D
Altretamine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -1.7631   -3.2830   -0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098   -2.4121    0.3640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111   -2.7618    1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -1.1740    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.0173   -0.0646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    1.1550   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716    2.3077   -0.4611 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    3.2072    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0580    2.5563   -1.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883    1.2194   -0.2580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.0751   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.0742    0.0076 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473    0.2570    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232   -0.1051   -1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.0879    0.1586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -2.7719   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467   -3.5612   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267   -4.2619   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249   -3.6501    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -1.8436    2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771   -2.8482    2.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5820    3.8423    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    3.9122    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7559    2.6658    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1181    3.6696   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017    2.1264   -1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826    2.1214   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109    0.0520    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483   -0.3880    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    1.3376    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5819   -0.4127   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -0.8861   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    0.8856   -1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  2  0
 15  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 488                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.081   2.695   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       9.748  -1.925   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       4.414  -1.925   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.415   0.385   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.747   0.385   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081  -1.925   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081   1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747   3.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748  -3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -1.155   0.000  0.00  0.00           C+0
CONECT    1    7   10   11                                                  
CONECT    2    8   12   13                                                  
CONECT    3    9   14   15                                                  
CONECT    4    7    8                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    1    4    5                                                  
CONECT    8    2    4    6                                                  
CONECT    9    3    5    6                                                  
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    2                                                            
CONECT   13    2                                                            
CONECT   14    3                                                            
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0014631
HETATM    1  C1  UNL     1      -1.763  -3.283  -0.699  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.310  -2.412   0.364  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.511  -2.762   1.777  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.639  -1.174   0.153  1.00  0.00           C  
HETATM    5  N2  UNL     1      -1.289  -0.017  -0.065  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.678   1.155  -0.265  1.00  0.00           C  
HETATM    7  N3  UNL     1      -1.472   2.308  -0.461  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.686   3.207   0.633  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.058   2.556  -1.754  1.00  0.00           C  
HETATM   10  N4  UNL     1       0.688   1.219  -0.258  1.00  0.00           N  
HETATM   11  C7  UNL     1       1.356   0.075  -0.041  1.00  0.00           C  
HETATM   12  N5  UNL     1       2.774   0.074   0.008  1.00  0.00           N  
HETATM   13  C8  UNL     1       3.447   0.257   1.269  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.523  -0.105  -1.213  1.00  0.00           C  
HETATM   15  N6  UNL     1       0.716  -1.088   0.159  1.00  0.00           N  
HETATM   16  H1  UNL     1      -1.609  -2.772  -1.661  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.847  -3.561  -0.566  1.00  0.00           H  
HETATM   18  H3  UNL     1      -1.227  -4.262  -0.691  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.125  -3.650   1.909  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.941  -1.844   2.233  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.477  -2.848   2.224  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.582   3.842   0.552  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.825   3.912   0.712  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.756   2.666   1.620  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.118   3.670  -1.855  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.102   2.126  -1.711  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.483   2.121  -2.597  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.511   0.052   1.159  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.048  -0.388   2.078  1.00  0.00           H  
HETATM   30  H15 UNL     1       3.331   1.338   1.548  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.582  -0.413  -1.007  1.00  0.00           H  
HETATM   32  H17 UNL     1       2.996  -0.886  -1.798  1.00  0.00           H  
HETATM   33  H18 UNL     1       3.521   0.886  -1.756  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5    5   15
CONECT    5    6
CONECT    6    7   10   10
CONECT    7    8    9
CONECT    8   22   23   24
CONECT    9   25   26   27
CONECT   10   11
CONECT   11   12   15   15
CONECT   12   13   14
CONECT   13   28   29   30
CONECT   14   31   32   33
END

HMDB0014631
     RDKit          3D
Altretamine
 33 33  0  0  0  0  0  0  0  0999 V2000
   -1.7631   -3.2830   -0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098   -2.4121    0.3640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111   -2.7618    1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -1.1740    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.0173   -0.0646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    1.1550   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4716    2.3077   -0.4611 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    3.2072    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0580    2.5563   -1.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883    1.2194   -0.2580 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.0751   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7744    0.0742    0.0076 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473    0.2570    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232   -0.1051   -1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.0879    0.1586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -2.7719   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467   -3.5612   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267   -4.2619   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249   -3.6501    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -1.8436    2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771   -2.8482    2.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5820    3.8423    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    3.9122    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7559    2.6658    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1181    3.6696   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017    2.1264   -1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826    2.1214   -2.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109    0.0520    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483   -0.3880    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    1.3376    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5819   -0.4127   -1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -0.8861   -1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    0.8856   -1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  2  0
 15  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4,6-Tris(dimethylamino)-1,3,5-triazine	ChEBI
2,4,6-Tris(dimethylamino)-S-triazine	ChEBI
Altretamina	ChEBI
Altretaminum	ChEBI
Hexalen	ChEBI
Hexastat	ChEBI
HMM	ChEBI
HEXAMETHYLMELAMINE	HMDB
HTM	HMDB
HXM	HMDB
Bellon brand OF altretamine	HMDB
Chiesi brand OF altretamine	HMDB
MGI pharma brand OF altretamine	HMDB
Rhône poulenc rorer brand OF altretamine	HMDB
Altretamine bellon brand	HMDB
Altretamine chiesi brand	HMDB
Hexinawas	HMDB
Wassermann brand OF altretamine	HMDB
Hemel	HMDB
Altretamine wassermann brand	HMDB
Rhône-poulenc rorer brand OF altretamine	HMDB
Altretamine	ChEBI

Chemical Formula

C₉H₁₈N₆

Average Molecular Weight

210.2794

Monoisotopic Molecular Weight

210.159294606

IUPAC Name

N2,N2,N4,N4,N6,N6-hexamethyl-1,3,5-triazine-2,4,6-triamine

Traditional Name

altretamine

CAS Registry Number

645-05-6

SMILES

CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C

InChI Identifier

InChI=1S/C9H18N6/c1-13(2)7-10-8(14(3)4)12-9(11-7)15(5)6/h1-6H3

InChI Key

UUVWYPNAQBNQJQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylarylamines

Alternative Parents

Substituents

Dialkylarylamine
N-aliphatic s-triazine
Aminotriazine
Amino-1,3,5-triazine
1,3,5-triazine
Triazine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

triamino-1,3,5-triazine (CHEBI:24564 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014631)

Source

Exogenous

Exogenous (HMDB: HMDB0014631)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	172 - 174 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.1 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	145.612	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000713

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.1 g/L	ALOGPS
logP	2.43	ALOGPS
logP	2.22	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	7.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.65 m³·mol⁻¹	ChemAxon
Polarizability	23.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	149.92	31661259
DarkChem	[M-H]-	149.183	31661259
DeepCCS	[M+H]+	152.852	30932474
DeepCCS	[M-H]-	150.457	30932474
DeepCCS	[M-2H]-	183.719	30932474
DeepCCS	[M+Na]+	158.884	30932474
AllCCS	[M+H]+	149.1	32859911
AllCCS	[M+H-H2O]+	145.6	32859911
AllCCS	[M+NH4]+	152.4	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	149.8	32859911
AllCCS	[M+Na-2H]-	150.8	32859911
AllCCS	[M+HCOO]-	152.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Altretamine	CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C	1929.9	Standard polar	33892256
Altretamine	CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C	1695.2	Standard non polar	33892256
Altretamine	CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C	1663.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Altretamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-7790000000-e6026ce486911f432231	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Altretamine 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 - Altretamine LC-ESI-qTof , Positive-QTOF	splash10-03dj-9781100000-4553bbbe9a30a0391bb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Altretamine , positive-QTOF	splash10-03di-3490000000-4af5631898604d2cec10	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Altretamine , positive-QTOF	splash10-03dj-9781100000-4553bbbe9a30a0391bb4	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 10V, Positive-QTOF	splash10-03di-0090000000-d69cd870b4294e5bc170	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 20V, Positive-QTOF	splash10-03di-0090000000-eab4cf11b3d7c71c506a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 40V, Positive-QTOF	splash10-03di-1890000000-772056487934c472a76f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 10V, Negative-QTOF	splash10-0a4i-0090000000-72599b7d9a667dc24339	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 20V, Negative-QTOF	splash10-0a4i-0190000000-18a5954520aa78e7f71a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 40V, Negative-QTOF	splash10-0a4l-0940000000-1d4df681882fc50a1202	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 10V, Negative-QTOF	splash10-0a4i-0090000000-a14cd1e86a35ad0351f1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 20V, Negative-QTOF	splash10-0a4i-0090000000-517d269b99785ef1fe2a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 40V, Negative-QTOF	splash10-0udl-3900000000-7516b289587ed30b86d1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 10V, Positive-QTOF	splash10-03di-0090000000-0434331ef81b820cb7f0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 20V, Positive-QTOF	splash10-03di-0090000000-0434331ef81b820cb7f0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Altretamine 40V, Positive-QTOF	splash10-01ba-9100000000-f88e708bc1bf0a456d92	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00488	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00488	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00488

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001629

KNApSAcK ID

C00008231

Chemspider ID

2038

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Altretamine

METLIN ID

Not Available

PubChem Compound

2123

PDB ID

Not Available

ChEBI ID

24564

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Damia G, D'Incalci M: Clinical pharmacokinetics of altretamine. Clin Pharmacokinet. 1995 Jun;28(6):439-48. [PubMed:7656502 ]
Malik IA: Altretamine is an effective palliative therapy of patients with recurrent epithelial ovarian cancer. Jpn J Clin Oncol. 2001 Feb;31(2):69-73. [PubMed:11302345 ]
Keldsen N, Havsteen H, Vergote I, Bertelsen K, Jakobsen A: Altretamine (hexamethylmelamine) in the treatment of platinum-resistant ovarian cancer: a phase II study. Gynecol Oncol. 2003 Feb;88(2):118-22. [PubMed:12586589 ]
Chan JK, Loizzi V, Manetta A, Berman ML: Oral altretamine used as salvage therapy in recurrent ovarian cancer. Gynecol Oncol. 2004 Jan;92(1):368-71. [PubMed:14751188 ]

Showing metabocard for Altretamine (HMDB0014631)

MOL for HMDB0014631 (Altretamine)

3D MOL for HMDB0014631 (Altretamine)

3D SDF for HMDB0014631 (Altretamine)

3D-SDF for HMDB0014631 (Altretamine)

PDB for HMDB0014631 (Altretamine)

3D PDB for HMDB0014631 (Altretamine)

SMILES for HMDB0014631 (Altretamine)

INCHI for HMDB0014631 (Altretamine)

Structure for HMDB0014631 (Altretamine)

3D Structure for HMDB0014631 (Altretamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra