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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:43:51 UTC

Update Date

2022-11-23 21:39:02 UTC

HMDB ID

HMDB0245675

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-Razoxane

Description

razoxane, also known as cardioxane, 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 razoxane. This compound has been identified in human blood as reported by (PMID: 31557052 ). (r)-razoxane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (R)-Razoxane 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

HMDB0245675
     RDKit          3D
Razoxane, (R)-
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.1544    2.0877   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    0.5956   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4308   -0.1950   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968   -0.0887   -0.4333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931   -0.8601   -1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -0.5729   -0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596   -0.8658   -1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3357    0.0194    0.4254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.0183    1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4288    0.4018    2.5683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.6031    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    0.5599   -0.6650 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372    1.2749    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9300    0.4415    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867    1.0170    0.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8361   -0.9798    0.6952 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706   -1.5937   -0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719   -2.8015   -0.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877   -0.6738   -1.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    2.5735    0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358    2.1948   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5935    2.5874   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6091    0.2369    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1664   -1.2826   -0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438   -0.0312   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5350   -1.9368   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5936   -2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422    0.4725    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.3940    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703   -1.7083    0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    2.0659   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    1.7860    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129   -1.5343    1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313   -0.4389   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -1.1423   -1.7961 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 11  4  1  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
M  END


  Mrv1533004241521132D          

 19 20  0  0  0  0            999 V2000
    0.0000   -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
    1.4289   -1.6500    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   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
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245675

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)

> <INCHI_KEY>
BMKDZUISNHGIBY-UHFFFAOYSA-N

> <FORMULA>
C11H16N4O4

> <MOLECULAR_WEIGHT>
268.273

> <EXACT_MASS>
268.117155011

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.505709186794277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-2.6526549413333336

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.800852844190322

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.198792840713974

> <JCHEM_PKA_STRONGEST_BASIC>
3.595816919458805

> <JCHEM_POLAR_SURFACE_AREA>
98.82

> <JCHEM_REFRACTIVITY>
64.2532

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
razoxane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245675
     RDKit          3D
Razoxane, (R)-
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.1544    2.0877   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    0.5956   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4308   -0.1950   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968   -0.0887   -0.4333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931   -0.8601   -1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -0.5729   -0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596   -0.8658   -1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3357    0.0194    0.4254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.0183    1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4288    0.4018    2.5683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.6031    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    0.5599   -0.6650 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372    1.2749    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9300    0.4415    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867    1.0170    0.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8361   -0.9798    0.6952 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706   -1.5937   -0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719   -2.8015   -0.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877   -0.6738   -1.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    2.5735    0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358    2.1948   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5935    2.5874   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6091    0.2369    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1664   -1.2826   -0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438   -0.0312   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5350   -1.9368   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5936   -2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422    0.4725    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.3940    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703   -1.7083    0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    2.0659   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    1.7860    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129   -1.5343    1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313   -0.4389   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -1.1423   -1.7961 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 11  4  1  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.667  -7.700   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    2   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0245675
HETATM    1  C1  UNL     1       0.154   2.088  -0.078  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.541   0.596  -0.071  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.431  -0.195  -0.904  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.797  -0.089  -0.433  1.00  0.00           N  
HETATM    5  C4  UNL     1      -2.693  -0.860  -1.299  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.085  -0.573  -0.842  1.00  0.00           C  
HETATM    7  O1  UNL     1      -5.060  -0.866  -1.602  1.00  0.00           O  
HETATM    8  N2  UNL     1      -4.336   0.019   0.425  1.00  0.00           N  
HETATM    9  C6  UNL     1      -3.292  -0.018   1.391  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.429   0.402   2.568  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.988  -0.603   0.906  1.00  0.00           C  
HETATM   12  N3  UNL     1       1.856   0.560  -0.665  1.00  0.00           N  
HETATM   13  C8  UNL     1       2.837   1.275   0.104  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.930   0.441   0.611  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.987   1.017   0.984  1.00  0.00           O  
HETATM   16  N4  UNL     1       3.836  -0.980   0.695  1.00  0.00           N  
HETATM   17  C10 UNL     1       2.871  -1.594  -0.185  1.00  0.00           C  
HETATM   18  O4  UNL     1       2.572  -2.802  -0.079  1.00  0.00           O  
HETATM   19  C11 UNL     1       2.288  -0.674  -1.194  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.491   2.573   0.860  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.936   2.195  -0.161  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.593   2.587  -0.963  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.609   0.237   0.964  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.166  -1.283  -0.722  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.344  -0.031  -1.979  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.535  -1.937  -1.197  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.588  -0.594  -2.351  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.242   0.472   0.667  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.187  -0.394   1.609  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.170  -1.708   0.802  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.271   2.066  -0.542  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.380   1.786   0.996  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.413  -1.534   1.335  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.131  -0.439  -1.916  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.517  -1.142  -1.796  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   12   23
CONECT    3    4   24   25
CONECT    4    5   11
CONECT    5    6   26   27
CONECT    6    7    7    8
CONECT    8    9   28
CONECT    9   10   10   11
CONECT   11   29   30
CONECT   12   13   19
CONECT   13   14   31   32
CONECT   14   15   15   16
CONECT   16   17   33
CONECT   17   18   18   19
CONECT   19   34   35
END

HMDB0245675
     RDKit          3D
Razoxane, (R)-
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.1544    2.0877   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    0.5956   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4308   -0.1950   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968   -0.0887   -0.4333 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931   -0.8601   -1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846   -0.5729   -0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596   -0.8658   -1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3357    0.0194    0.4254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.0183    1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4288    0.4018    2.5683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -0.6031    0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    0.5599   -0.6650 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372    1.2749    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9300    0.4415    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867    1.0170    0.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8361   -0.9798    0.6952 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706   -1.5937   -0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719   -2.8015   -0.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877   -0.6738   -1.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    2.5735    0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358    2.1948   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5935    2.5874   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6091    0.2369    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1664   -1.2826   -0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438   -0.0312   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5350   -1.9368   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -0.5936   -2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422    0.4725    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -0.3940    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703   -1.7083    0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    2.0659   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    1.7860    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129   -1.5343    1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313   -0.4389   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -1.1423   -1.7961 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 11  4  1  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+,-)-1,2-Bis(3,5-dioxopiperazine-1-yl)propane	ChEBI
Razoxana	ChEBI
Razoxanum	ChEBI
Cardioxane	Kegg
Razoxane, (R)-isomer	MeSH
ICRF-159	MeSH
ICRF 159	MeSH
ICRF 186	MeSH
ICRF159	MeSH
Razoxane mesylate, (R)-isomer	MeSH
ICRF-186	MeSH
ICRF186	MeSH
Razoxin	MeSH

Chemical Formula

C₁₁H₁₆N₄O₄

Average Molecular Weight

268.273

Monoisotopic Molecular Weight

268.117155011

IUPAC Name

4-[2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione

Traditional Name

razoxane

CAS Registry Number

Not Available

SMILES

CC(CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1

InChI Identifier

InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)

InChI Key

BMKDZUISNHGIBY-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
Tertiary amine
Tertiary aliphatic amine
N-acylimine
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-alkylpiperazine (CHEBI:50225 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	-1	ALOGPS
logP	-2.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.2	ChemAxon
pKa (Strongest Basic)	3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.25 m³·mol⁻¹	ChemAxon
Polarizability	25.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.903	30932474
DeepCCS	[M-H]-	157.545	30932474
DeepCCS	[M-2H]-	190.431	30932474
DeepCCS	[M+Na]+	165.996	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.4	32859911
AllCCS	[M+Na]+	163.3	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	160.8	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Razoxane, (R)-	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1	3369.9	Standard polar	33892256
Razoxane, (R)-	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1	2313.5	Standard non polar	33892256
Razoxane, (R)-	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1	2522.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Razoxane, (R)-,1TMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2364.7	Semi standard non polar	33892256
Razoxane, (R)-,1TMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2709.2	Standard non polar	33892256
Razoxane, (R)-,1TMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	4420.0	Standard polar	33892256
Razoxane, (R)-,1TMS,isomer #2	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2340.3	Semi standard non polar	33892256
Razoxane, (R)-,1TMS,isomer #2	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2695.9	Standard non polar	33892256
Razoxane, (R)-,1TMS,isomer #2	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	4405.4	Standard polar	33892256
Razoxane, (R)-,2TMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2256.8	Semi standard non polar	33892256
Razoxane, (R)-,2TMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2701.9	Standard non polar	33892256
Razoxane, (R)-,2TMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	3681.4	Standard polar	33892256
Razoxane, (R)-,1TBDMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2609.3	Semi standard non polar	33892256
Razoxane, (R)-,1TBDMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2937.3	Standard non polar	33892256
Razoxane, (R)-,1TBDMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	4383.1	Standard polar	33892256
Razoxane, (R)-,1TBDMS,isomer #2	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	2598.5	Semi standard non polar	33892256
Razoxane, (R)-,1TBDMS,isomer #2	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	2928.2	Standard non polar	33892256
Razoxane, (R)-,1TBDMS,isomer #2	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	4363.3	Standard polar	33892256
Razoxane, (R)-,2TBDMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	2728.2	Semi standard non polar	33892256
Razoxane, (R)-,2TBDMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	3116.0	Standard non polar	33892256
Razoxane, (R)-,2TBDMS,isomer #1	CC(CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	3578.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Razoxane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0m2c-4910000000-46d13032d5f2c6472d9b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Razoxane 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 - (R)-Razoxane 10V, Positive-QTOF	splash10-014i-0490000000-80b0b21a495d2cc911a4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 20V, Positive-QTOF	splash10-0a4i-1910000000-5a4bec9ae0f631c4c328	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 40V, Positive-QTOF	splash10-052b-8900000000-da472776fdfa9ff649dd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 10V, Negative-QTOF	splash10-014i-0090000000-3ed9d12564a96e4f79a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 20V, Negative-QTOF	splash10-0006-9010000000-913da0d82e09de14ca70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 40V, Negative-QTOF	splash10-0006-9100000000-1b65fef6f408f48c6b59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 10V, Positive-QTOF	splash10-0a4i-0910000000-8bbf646c07221a874c7c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 20V, Positive-QTOF	splash10-0aor-3790000000-825583366aa2049c6487	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 40V, Positive-QTOF	splash10-0abc-9610000000-e2da7526d67ac758a836	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 10V, Negative-QTOF	splash10-014i-0090000000-bd2978e4c0725b5d29bd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 20V, Negative-QTOF	splash10-05p6-5890000000-a1cb5b2cd96d828fbdaa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Razoxane 40V, Negative-QTOF	splash10-0006-9400000000-50d8c9f710f08bb20677	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

28423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dexrazoxane

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

50225

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 ]

Showing metabocard for (R)-Razoxane (HMDB0245675)

MOL for HMDB0245675 ((R)-Razoxane)

3D MOL for HMDB0245675 ((R)-Razoxane)

3D SDF for HMDB0245675 ((R)-Razoxane)

3D-SDF for HMDB0245675 ((R)-Razoxane)

PDB for HMDB0245675 ((R)-Razoxane)

3D PDB for HMDB0245675 ((R)-Razoxane)

SMILES for HMDB0245675 ((R)-Razoxane)

INCHI for HMDB0245675 ((R)-Razoxane)

Structure for HMDB0245675 ((R)-Razoxane)

3D Structure for HMDB0245675 ((R)-Razoxane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra