Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:41:02 UTC

Update Date

2021-10-01 19:54:45 UTC

HMDB ID

HMDB0250591

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cuprizone

Description

Cuprizone belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a significant number of articles have been published on Cuprizone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cuprizone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cuprizone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250591
     RDKit          3D
Cuprizone
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.6511   -1.3296   -0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8183   -0.4768   -0.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509   -0.4026   -1.6312 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0905   -1.2911   -1.3055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093   -1.1560   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984   -0.0455    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886    0.8774    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9769    0.1060    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0184   -1.3146    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8849   -2.1355    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    0.4436   -1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    1.3168   -2.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    0.3659   -0.5860 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5300    1.2239   -0.8717 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263    0.8313   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576   -0.5176   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4494   -0.7088    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9908    0.4424    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8937    1.7565    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8549    1.7459   -0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2453    0.2770   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431    0.4883    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808   -0.4810    1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    1.2831    1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    1.7102   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    0.0980   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8893    0.6088    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0022   -1.7525    0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8396   -1.3326    1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6070   -2.9206    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902   -2.5868   -0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112   -0.3473    0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -0.5000    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4908   -1.3168   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.6337    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9663   -0.8038   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227    0.1906    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3807    0.5020    1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8823    1.9377   -0.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    2.5943    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402    1.4654   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4906    2.7879   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 10  5  1  0
 20 15  1  0
  3 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END


  Mrv1652309112109412D          

 20 21  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250591

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(NN=C1CCCCC1)C(=O)NN=C1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C14H22N4O2/c19-13(17-15-11-7-3-1-4-8-11)14(20)18-16-12-9-5-2-6-10-12/h1-10H2,(H,17,19)(H,18,20)

> <INCHI_KEY>
DSRJIHMZAQEUJV-UHFFFAOYSA-N

> <FORMULA>
C14H22N4O2

> <MOLECULAR_WEIGHT>
278.356

> <EXACT_MASS>
278.174275964

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.213374996767648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N',N'-dicyclohexylideneethanedihydrazide

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.0057526780000003

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.801080366705467

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.638202457857124

> <JCHEM_PKA_STRONGEST_BASIC>
1.936083040560899

> <JCHEM_POLAR_SURFACE_AREA>
82.92

> <JCHEM_REFRACTIVITY>
75.492

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N',N'-dicyclohexylideneethanedihydrazide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250591
     RDKit          3D
Cuprizone
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.6511   -1.3296   -0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8183   -0.4768   -0.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509   -0.4026   -1.6312 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0905   -1.2911   -1.3055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093   -1.1560   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984   -0.0455    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886    0.8774    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9769    0.1060    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0184   -1.3146    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8849   -2.1355    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    0.4436   -1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    1.3168   -2.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    0.3659   -0.5860 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5300    1.2239   -0.8717 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263    0.8313   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576   -0.5176   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4494   -0.7088    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9908    0.4424    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8937    1.7565    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8549    1.7459   -0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2453    0.2770   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431    0.4883    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808   -0.4810    1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    1.2831    1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    1.7102   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    0.0980   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8893    0.6088    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0022   -1.7525    0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8396   -1.3326    1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6070   -2.9206    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902   -2.5868   -0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112   -0.3473    0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -0.5000    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4908   -1.3168   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.6337    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9663   -0.8038   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227    0.1906    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3807    0.5020    1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8823    1.9377   -0.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    2.5943    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402    1.4654   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4906    2.7879   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 10  5  1  0
 20 15  1  0
  3 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       8.002  -4.620   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2   20                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    4   20                                                       
CONECT   20   19    1                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0250591
HETATM    1  O1  UNL     1      -0.651  -1.330  -0.037  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.818  -0.477  -0.938  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.051  -0.403  -1.631  1.00  0.00           N  
HETATM    4  N2  UNL     1      -3.091  -1.291  -1.305  1.00  0.00           N  
HETATM    5  C2  UNL     1      -3.809  -1.156  -0.266  1.00  0.00           C  
HETATM    6  C3  UNL     1      -3.598  -0.046   0.678  1.00  0.00           C  
HETATM    7  C4  UNL     1      -4.789   0.877   0.619  1.00  0.00           C  
HETATM    8  C5  UNL     1      -5.977   0.106   0.101  1.00  0.00           C  
HETATM    9  C6  UNL     1      -6.018  -1.315   0.642  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.885  -2.135   0.005  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.252   0.444  -1.278  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.121   1.317  -2.182  1.00  0.00           O  
HETATM   13  N3  UNL     1       1.470   0.366  -0.586  1.00  0.00           N  
HETATM   14  N4  UNL     1       2.530   1.224  -0.872  1.00  0.00           N  
HETATM   15  C9  UNL     1       3.726   0.831  -0.642  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.958  -0.518  -0.080  1.00  0.00           C  
HETATM   17  C11 UNL     1       5.449  -0.709   0.061  1.00  0.00           C  
HETATM   18  C12 UNL     1       5.991   0.442   0.871  1.00  0.00           C  
HETATM   19  C13 UNL     1       5.894   1.756   0.144  1.00  0.00           C  
HETATM   20  C14 UNL     1       4.855   1.746  -0.945  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.245   0.277  -2.380  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.643   0.488   0.496  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.581  -0.481   1.717  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.979   1.283   1.646  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.532   1.710  -0.086  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.034   0.098  -0.998  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.889   0.609   0.536  1.00  0.00           H  
HETATM   28  H8  UNL     1      -7.002  -1.752   0.423  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.840  -1.333   1.728  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.607  -2.921   0.719  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.290  -2.587  -0.923  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.611  -0.347   0.171  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.548  -0.500   0.961  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.491  -1.317  -0.690  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.641  -1.634   0.662  1.00  0.00           H  
HETATM   36  H16 UNL     1       5.966  -0.804  -0.916  1.00  0.00           H  
HETATM   37  H17 UNL     1       7.023   0.191   1.178  1.00  0.00           H  
HETATM   38  H18 UNL     1       5.381   0.502   1.795  1.00  0.00           H  
HETATM   39  H19 UNL     1       6.882   1.938  -0.328  1.00  0.00           H  
HETATM   40  H20 UNL     1       5.711   2.594   0.834  1.00  0.00           H  
HETATM   41  H21 UNL     1       5.340   1.465  -1.905  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.491   2.788  -1.063  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   21
CONECT    4    5    5
CONECT    5    6   10
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   28   29
CONECT   10   30   31
CONECT   11   12   12   13
CONECT   13   14   32
CONECT   14   15   15
CONECT   15   16   20
CONECT   16   17   33   34
CONECT   17   18   35   36
CONECT   18   19   37   38
CONECT   19   20   39   40
CONECT   20   41   42
END

HMDB0250591
     RDKit          3D
Cuprizone
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.6511   -1.3296   -0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8183   -0.4768   -0.9376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0509   -0.4026   -1.6312 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0905   -1.2911   -1.3055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093   -1.1560   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984   -0.0455    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886    0.8774    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9769    0.1060    0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0184   -1.3146    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8849   -2.1355    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2517    0.4436   -1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    1.3168   -2.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697    0.3659   -0.5860 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5300    1.2239   -0.8717 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263    0.8313   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576   -0.5176   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4494   -0.7088    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9908    0.4424    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8937    1.7565    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8549    1.7459   -0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2453    0.2770   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431    0.4883    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808   -0.4810    1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    1.2831    1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324    1.7102   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    0.0980   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8893    0.6088    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0022   -1.7525    0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8396   -1.3326    1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6070   -2.9206    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902   -2.5868   -0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112   -0.3473    0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -0.5000    0.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4908   -1.3168   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.6337    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9663   -0.8038   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227    0.1906    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3807    0.5020    1.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8823    1.9377   -0.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    2.5943    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402    1.4654   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4906    2.7879   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 10  5  1  0
 20 15  1  0
  3 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Biscyclohexanone oxaldihydrazone	HMDB
Oxaldihydrazone, biscyclohexanone	HMDB

Chemical Formula

C₁₄H₂₂N₄O₂

Average Molecular Weight

278.356

Monoisotopic Molecular Weight

278.174275964

IUPAC Name

N',N'-dicyclohexylideneethanedihydrazide

Traditional Name

N',N'-dicyclohexylideneethanedihydrazide

CAS Registry Number

Not Available

SMILES

O=C(NN=C1CCCCC1)C(=O)NN=C1CCCCC1

InChI Identifier

InChI=1S/C14H22N4O2/c19-13(17-15-11-7-3-1-4-8-11)14(20)18-16-12-9-5-2-6-10-12/h1-10H2,(H,17,19)(H,18,20)

InChI Key

DSRJIHMZAQEUJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Semioxamazone
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

a small molecule (CUPRIZONE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	2.32	ALOGPS
logP	2.01	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.64	ChemAxon
pKa (Strongest Basic)	1.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.49 m³·mol⁻¹	ChemAxon
Polarizability	30.21 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	167.008	30932474
DeepCCS	[M-H]-	164.65	30932474
DeepCCS	[M-2H]-	197.748	30932474
DeepCCS	[M+Na]+	173.101	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	19.4512 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2816.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	555.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	314.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	503.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	768.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	948.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	149.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1807.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	507.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1702.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	545.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	444.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	586.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	485.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	15.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cuprizone	O=C(NN=C1CCCCC1)C(=O)NN=C1CCCCC1	2593.8	Standard polar	33892256
Cuprizone	O=C(NN=C1CCCCC1)C(=O)NN=C1CCCCC1	2205.9	Standard non polar	33892256
Cuprizone	O=C(NN=C1CCCCC1)C(=O)NN=C1CCCCC1	2660.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cuprizone,1TMS,isomer #1	C[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)NN=C1CCCCC1	2597.7	Semi standard non polar	33892256
Cuprizone,1TMS,isomer #1	C[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)NN=C1CCCCC1	2374.9	Standard non polar	33892256
Cuprizone,1TMS,isomer #1	C[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)NN=C1CCCCC1	4280.4	Standard polar	33892256
Cuprizone,2TMS,isomer #1	C[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)N(N=C1CCCCC1)[Si](C)(C)C	2530.5	Semi standard non polar	33892256
Cuprizone,2TMS,isomer #1	C[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)N(N=C1CCCCC1)[Si](C)(C)C	2337.0	Standard non polar	33892256
Cuprizone,2TMS,isomer #1	C[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)N(N=C1CCCCC1)[Si](C)(C)C	3853.5	Standard polar	33892256
Cuprizone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)NN=C1CCCCC1	2758.9	Semi standard non polar	33892256
Cuprizone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)NN=C1CCCCC1	2565.5	Standard non polar	33892256
Cuprizone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)NN=C1CCCCC1	4323.3	Standard polar	33892256
Cuprizone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)N(N=C1CCCCC1)[Si](C)(C)C(C)(C)C	2872.4	Semi standard non polar	33892256
Cuprizone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)N(N=C1CCCCC1)[Si](C)(C)C(C)(C)C	2688.1	Standard non polar	33892256
Cuprizone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(N=C1CCCCC1)C(=O)C(=O)N(N=C1CCCCC1)[Si](C)(C)C(C)(C)C	3807.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cuprizone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000m-9540000000-10333b236931676fe88e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cuprizone 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuprizone 10V, Positive-QTOF	splash10-004i-0390000000-b4c4c5ff2e60bb9ad8e1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuprizone 20V, Positive-QTOF	splash10-005i-8890000000-46ed014cfb17fa4beb7f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuprizone 40V, Positive-QTOF	splash10-001j-9210000000-b063d7a0119bc999d5fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuprizone 10V, Negative-QTOF	splash10-004i-0090000000-3c39745ae26b45026e28	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuprizone 20V, Negative-QTOF	splash10-004m-9880000000-1641a9359d36dfde234c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cuprizone 40V, Negative-QTOF	splash10-0006-9000000000-c9358d91bf52d9564c90	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9341

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9723

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. Nuclear protein 1

General function:: Not Available
Specific function:: Transcription regulator that converts stress signals into a program of gene expression that empowers cells with resistance to the stress induced by a change in their microenvironment. Thereby participates in regulation of many process namely cell-cycle, apoptosis, autophagy and DNA repair responses (PubMed:16478804, PubMed:19650074, PubMed:16300740, PubMed:19723804, PubMed:11056169, PubMed:22858377, PubMed:11940591, PubMed:18690848, PubMed:22565310, PubMed:20181828, PubMed:30451898). Controls cell cycle progression and protects cells from genotoxic stress induced by doxorubicin through the complex formation with TP53 and EP300 that binds CDKN1A promoter leading to transcriptional induction of CDKN1A (PubMed:18690848). Protects pancreatic cancer cells from stress-induced cell death by binding the RELB promoter and activating its transcription, leading to IER3 transactivation (PubMed:22565310). Negatively regulates apoptosis through interaction with PTMA (PubMed:16478804). Inhibits autophagy-induced apoptosis in cardiac cells through FOXO3 interaction, inducing cytoplasmic translocation of FOXO3 thereby preventing the FOXO3 association with the pro-autophagic BNIP3 promoter (PubMed:20181828). Inhibits cell growth and facilitates programmed cell death by apoptosis after adriamycin-induced DNA damage through transactivation of TP53 (By similarity). Regulates methamphetamine-induced apoptosis and autophagy through DDIT3-mediated endoplasmic reticulum stress pathway (By similarity). Participates in DNA repair following gamma-irradiation by facilitating DNA access of the transcription machinery through interaction with MSL1 leading to inhibition of histone H4' Lys-16' acetylation (H4K16ac) (PubMed:19650074). Coactivator of PAX2 transcription factor activity, both by recruiting EP300 to increase PAX2 transcription factor activity and by binding PAXIP1 to suppress PAXIP1-induced inhibition on PAX2 (PubMed:11940591). Positively regulates cell cycle progression through interaction with COPS5 inducing cytoplasmic translocation of CDKN1B leading to the CDKN1B degradation (PubMed:16300740). Coordinates, through its interaction with EP300, the assiociation of MYOD1, EP300 and DDX5 to the MYOG promoter, leading to inhibition of cell-cycle progression and myogenic differentiation promotion (PubMed:19723804). Negatively regulates beta cell proliferation via inhibition of cell-cycle regulatory genes expression through the suppression of their promoter activities (By similarity). Also required for LHB expression and ovarian maturation (By similarity). Exacerbates CNS inflammation and demyelination upon cuprizone treatment (By similarity).
Gene Name:: NUPR1
Uniprot ID:: O60356
Molecular weight:: 8872.695

Showing metabocard for Cuprizone (HMDB0250591)

MOL for HMDB0250591 (Cuprizone)

3D MOL for HMDB0250591 (Cuprizone)

3D SDF for HMDB0250591 (Cuprizone)

3D-SDF for HMDB0250591 (Cuprizone)

PDB for HMDB0250591 (Cuprizone)

3D PDB for HMDB0250591 (Cuprizone)

SMILES for HMDB0250591 (Cuprizone)

INCHI for HMDB0250591 (Cuprizone)

Structure for HMDB0250591 (Cuprizone)

3D Structure for HMDB0250591 (Cuprizone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes