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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

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014381

Secondary Accession Numbers

HMDB14381

Metabolite Identification

Common Name

Pipobroman

Description

Pipobroman, also known as vercyte or a 8103, belongs to the class of organic compounds known as piperazines. Piperazines are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms. Pipobroman is a drug which is used for the treatment of polycythaemia vera and refractory chronic myeloid leukaemia. Based on a literature review a significant number of articles have been published on Pipobroman.

Structure

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

HMDB0014381
     RDKit          3D
Pipobroman
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1287   -1.9892    0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701   -0.9775    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    0.0139   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537   -0.3413   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1577    1.0823   -0.8388 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669   -0.8244    0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615   -1.8148    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.1276    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268   -0.1559    0.3470 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655    0.2684    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4151   -0.2171    1.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    1.2561   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8376    1.5439    0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9699    0.0079    0.0270 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    0.4179   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7692    0.3424   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    1.0433    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    0.1310   -1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120   -1.2584   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709   -0.3770    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -2.4136   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8182   -2.5137    1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122   -1.8818    1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212   -0.5691    2.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    2.2344   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407    0.9056   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426    2.2803   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296    2.0323    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    1.4847   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618   -0.1063   -1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1851    0.2974   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592    1.2258   -0.1931 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  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  0
 15 16  1  0
 16  6  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
M  END

236
  Mrv0541 02231214322D          

 16 16  0  0  0  0            999 V2000
    1.6500   -3.3000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    3.3000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 16  1  0  0  0  0
  3 11  2  0  0  0  0
  4 12  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014381

> <DATABASE_NAME>
hmdb

> <SMILES>
BrCCC(=O)N1CCN(CC1)C(=O)CCBr

> <INCHI_IDENTIFIER>
InChI=1S/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2

> <INCHI_KEY>
NJBFOOCLYDNZJN-UHFFFAOYSA-N

> <FORMULA>
C10H16Br2N2O2

> <MOLECULAR_WEIGHT>
356.054

> <EXACT_MASS>
353.95785306

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.439271640930805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one

> <ALOGPS_LOGP>
1.09

> <JCHEM_LOGP>
0.4107813379999997

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7181493734636274

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
69.45280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pipobroman

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014381
     RDKit          3D
Pipobroman
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1287   -1.9892    0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701   -0.9775    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    0.0139   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537   -0.3413   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1577    1.0823   -0.8388 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669   -0.8244    0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615   -1.8148    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.1276    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268   -0.1559    0.3470 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655    0.2684    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4151   -0.2171    1.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    1.2561   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8376    1.5439    0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9699    0.0079    0.0270 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    0.4179   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7692    0.3424   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    1.0433    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    0.1310   -1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120   -1.2584   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709   -0.3770    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -2.4136   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8182   -2.5137    1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122   -1.8818    1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212   -0.5691    2.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    2.2344   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407    0.9056   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426    2.2803   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296    2.0323    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    1.4847   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618   -0.1063   -1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1851    0.2974   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592    1.2258   -0.1931 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  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  0
 15 16  1  0
 16  6  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 236                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       3.080  -6.160   0.000  0.00  0.00          Br+0
HETATM    2 Br   UNK     0       8.415   6.160   0.000  0.00  0.00          Br+0
HETATM    3  O   UNK     0       7.081  -3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414   3.850   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.747  -1.540   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.747   1.540   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   5.390   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    7    8   11                                                  
CONECT    6    9   10   12                                                  
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    6    7                                                       
CONECT   10    6    8                                                       
CONECT   11    3    5   13                                                  
CONECT   12    4    6   14                                                  
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15    1   13                                                       
CONECT   16    2   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0014381
HETATM    1  O1  UNL     1      -3.129  -1.989   0.759  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.670  -0.977   0.171  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.631   0.014  -0.346  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.054  -0.341  -0.085  1.00  0.00           C  
HETATM    5 BR1  UNL     1      -6.158   1.082  -0.839  1.00  0.00          BR  
HETATM    6  N1  UNL     1      -1.267  -0.824   0.026  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.361  -1.815   0.544  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.785  -1.128   1.214  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.427  -0.156   0.347  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.765   0.268   0.536  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.415  -0.217   1.488  1.00  0.00           O  
HETATM   12  C7  UNL     1       3.427   1.256  -0.340  1.00  0.00           C  
HETATM   13  C8  UNL     1       4.838   1.544   0.058  1.00  0.00           C  
HETATM   14 BR2  UNL     1       5.970   0.008   0.027  1.00  0.00          BR  
HETATM   15  C9  UNL     1       0.703   0.418  -0.755  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.769   0.342  -0.651  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.440   1.043   0.069  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.517   0.131  -1.460  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.312  -1.258  -0.610  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.271  -0.377   1.006  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.022  -2.414  -0.323  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.818  -2.514   1.245  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.512  -1.882   1.594  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.421  -0.569   2.105  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.879   2.234  -0.335  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.441   0.906  -1.404  1.00  0.00           H  
HETATM   27  H11 UNL     1       5.243   2.280  -0.684  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.930   2.032   1.042  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.002   1.485  -0.824  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.062  -0.106  -1.681  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.185   0.297  -1.700  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.259   1.226  -0.193  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    6    7   16
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   10   15
CONECT   10   11   11   12
CONECT   12   13   25   26
CONECT   13   14   27   28
CONECT   15   16   29   30
CONECT   16   31   32
END

HMDB0014381
     RDKit          3D
Pipobroman
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.1287   -1.9892    0.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701   -0.9775    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    0.0139   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0537   -0.3413   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1577    1.0823   -0.8388 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669   -0.8244    0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615   -1.8148    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -1.1276    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268   -0.1559    0.3470 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655    0.2684    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4151   -0.2171    1.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    1.2561   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8376    1.5439    0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9699    0.0079    0.0270 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7030    0.4179   -0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7692    0.3424   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    1.0433    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    0.1310   -1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120   -1.2584   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709   -0.3770    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -2.4136   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8182   -2.5137    1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5122   -1.8818    1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212   -0.5691    2.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    2.2344   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407    0.9056   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426    2.2803   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296    2.0323    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    1.4847   -0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618   -0.1063   -1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1851    0.2974   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592    1.2258   -0.1931 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  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  0
 15 16  1  0
 16  6  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Bis(3-bromopropionyl)piperazine	ChEBI
a 8103	ChEBI
a-8103	ChEBI
Amedel	ChEBI
N,N-Bis-(3-bromopropionyl)-piperazine	ChEBI
Vercyte	ChEBI

Chemical Formula

C₁₀H₁₆Br₂N₂O₂

Average Molecular Weight

356.054

Monoisotopic Molecular Weight

353.95785306

IUPAC Name

3-bromo-1-[4-(3-bromopropanoyl)piperazin-1-yl]propan-1-one

Traditional Name

pipobroman

CAS Registry Number

54-91-1

SMILES

BrCCC(=O)N1CCN(CC1)C(=O)CCBr

InChI Identifier

InChI=1S/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2

InChI Key

NJBFOOCLYDNZJN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperazines. Piperazines are compounds containing a piperazine ring, which is a saturated aliphatic six-member heterocyclic with two nitrogen atoms at positions 1 and 4, as well as four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Piperazines

Alternative Parents

Substituents

Piperazine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Azacycle
Alkyl bromide
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alkyl halide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

phytanoyl-CoAs (CHEBI:8242 )

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: HMDB0014381)

Source

Exogenous

Exogenous (HMDB: HMDB0014381)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.24 g/L	Not Available
LogP	1.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.24 g/L	ALOGPS
logP	1.09	ALOGPS
logP	0.41	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-0.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.45 m³·mol⁻¹	ChemAxon
Polarizability	28.44 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
DeepCCS	[M+H]+	154.261	30932474
DeepCCS	[M-H]-	151.903	30932474
DeepCCS	[M-2H]-	185.869	30932474
DeepCCS	[M+Na]+	160.833	30932474
AllCCS	[M+H]+	166.6	32859911
AllCCS	[M+H-H2O]+	163.9	32859911
AllCCS	[M+NH4]+	169.2	32859911
AllCCS	[M+Na]+	169.9	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	166.2	32859911
AllCCS	[M+HCOO]-	167.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.84 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1142 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.99 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1201.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	244.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	135.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.0 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	424.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	264.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	825.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	268.0 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	1092.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	335.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	313.1 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	46.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pipobroman	BrCCC(=O)N1CCN(CC1)C(=O)CCBr	2673.3	Standard polar	33892256
Pipobroman	BrCCC(=O)N1CCN(CC1)C(=O)CCBr	1961.8	Standard non polar	33892256
Pipobroman	BrCCC(=O)N1CCN(CC1)C(=O)CCBr	2588.7	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 - Pipobroman GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-3980000000-8bd279e69119d9648d5b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pipobroman GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pipobroman 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 - Pipobroman 10V, Positive-QTOF	splash10-0udi-0139000000-aa4921fbff3c003c871f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 20V, Positive-QTOF	splash10-0ul0-4968000000-94fcf9b74b69619540e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 40V, Positive-QTOF	splash10-000i-9610000000-02d07b217917ecfc91e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 10V, Negative-QTOF	splash10-0udi-0129000000-23f3440e6b284425653f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 20V, Negative-QTOF	splash10-0uxr-0696000000-8158a82dd2fe379c501f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 40V, Negative-QTOF	splash10-01qi-7920000000-ab7db93bf44290624bec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 10V, Negative-QTOF	splash10-014i-1793000000-3de2c8d6716323b5962b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 20V, Negative-QTOF	splash10-00or-5892000000-9b2a25a7697cd7a2a25f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 40V, Negative-QTOF	splash10-004i-9000000000-28b4ae48a39b48af6c7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 10V, Positive-QTOF	splash10-0udi-0009000000-4265af251f045bf88819	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 20V, Positive-QTOF	splash10-0udi-0029000000-2a422250aab165cd7b1c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pipobroman 40V, Positive-QTOF	splash10-0006-9610000000-0cf247041481b787196c	2021-09-22	Wishart 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 DB00236	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00236	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00236

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4676

KEGG Compound ID

C07362

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pipobroman

METLIN ID

Not Available

PubChem Compound

4842

PDB ID

Not Available

ChEBI ID

8242

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

Not Available

Showing metabocard for Pipobroman (HMDB0014381)

MOL for HMDB0014381 (Pipobroman)

3D MOL for HMDB0014381 (Pipobroman)

3D SDF for HMDB0014381 (Pipobroman)

3D-SDF for HMDB0014381 (Pipobroman)

PDB for HMDB0014381 (Pipobroman)

3D PDB for HMDB0014381 (Pipobroman)

SMILES for HMDB0014381 (Pipobroman)

INCHI for HMDB0014381 (Pipobroman)

Structure for HMDB0014381 (Pipobroman)

3D Structure for HMDB0014381 (Pipobroman)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra