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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:35:57 UTC

Update Date

2021-09-26 23:11:46 UTC

HMDB ID

HMDB0256253

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pentaerythritol tetranitrate

Description

Pentaerythritol tetranitrate, also known as nitropenta or corpent, belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group. Pentaerythritol tetranitrate is a drug which is used for the treatment of angina pectoris [l2393]. Based on a literature review a significant number of articles have been published on Pentaerythritol tetranitrate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pentaerythritol tetranitrate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pentaerythritol tetranitrate 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

HMDB0256253
     RDKit          3D
Pentaerythritol tetranitrate
 29 28  0  0  0  0  0  0  0  0999 V2000
   -2.9976    1.9772    2.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    2.3748    1.6685 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6701    3.6979    1.7687 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2483    1.5426    0.9276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.5850    1.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -0.1036    0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870   -0.7443   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4188   -1.4133   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3270   -2.0549   -2.5150 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3920   -3.2912   -2.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -1.3517   -3.3094 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3034   -1.1096    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -2.1465    1.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204   -3.1132    1.7580 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.0099   -4.0244    0.9787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -3.0711    2.9996 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9251    0.9772   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    1.9311   -1.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234    2.9926   -1.8136 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.6040    3.1203   -2.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    3.9464   -2.1967 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.7912   -0.1322    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860    1.0915    1.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773   -0.0061   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -1.5098    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163   -1.5257   -0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160   -0.5572    1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3760    0.4964   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    1.4219    0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
 12 26  1  0
 12 27  1  0
 17 28  1  0
 17 29  1  0
M  CHG  8   2   1   3  -1   9   1  11  -1  14   1  16  -1  19   1  21  -1
M  END

  Mrv0541 02241204202D          

 21 20  0  0  0  0            999 V2000
    4.1474    0.4420    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.9575    0.2861    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.4976    0.9097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2276   -0.4935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0377   -0.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3077   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5778   -2.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3879   -2.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6580   -3.1440    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.4681   -3.2999    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.1179   -3.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5282   -1.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9046   -1.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.5014   -0.8889    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.9691   -2.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0873   -1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7109   -1.6990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4905   -1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.6464   -0.6188    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.1141   -1.9690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  CHG  8   1  -1   2   1   9   1  10  -1  14   1  15  -1  19   1  20  -1
M  END
> <DATABASE_ID>
HMDB0256253

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2

> <INCHI_KEY>
TZRXHJWUDPFEEY-UHFFFAOYSA-N

> <FORMULA>
C5H8N4O12

> <MOLECULAR_WEIGHT>
316.1366

> <EXACT_MASS>
316.01387174

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
22.46856229170519

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
0.961219707333333

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4611010401660485

> <JCHEM_POLAR_SURFACE_AREA>
220.19999999999996

> <JCHEM_REFRACTIVITY>
58.50370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentaerythritol tetranitrate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256253
     RDKit          3D
Pentaerythritol tetranitrate
 29 28  0  0  0  0  0  0  0  0999 V2000
   -2.9976    1.9772    2.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    2.3748    1.6685 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6701    3.6979    1.7687 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2483    1.5426    0.9276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.5850    1.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -0.1036    0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870   -0.7443   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4188   -1.4133   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3270   -2.0549   -2.5150 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3920   -3.2912   -2.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -1.3517   -3.3094 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3034   -1.1096    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -2.1465    1.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204   -3.1132    1.7580 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.0099   -4.0244    0.9787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -3.0711    2.9996 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9251    0.9772   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    1.9311   -1.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234    2.9926   -1.8136 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.6040    3.1203   -2.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    3.9464   -2.1967 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.7912   -0.1322    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860    1.0915    1.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773   -0.0061   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -1.5098    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163   -1.5257   -0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160   -0.5572    1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3760    0.4964   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    1.4219    0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
 12 26  1  0
 12 27  1  0
 17 28  1  0
 17 29  1  0
M  CHG  8   2   1   3  -1   9   1  11  -1  14   1  16  -1  19   1  21  -1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       7.742   0.825   0.000  0.00  0.00           O-1
HETATM    2  N   UNK     0       9.254   0.534   0.000  0.00  0.00           N+1
HETATM    3  O   UNK     0      10.262   1.698   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.758  -0.921   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.270  -1.212   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.774  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.279  -4.123   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.791  -4.414   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      14.295  -5.869   0.000  0.00  0.00           N+1
HETATM   10  O   UNK     0      15.807  -6.160   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0      13.287  -7.033   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.319  -3.171   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.155  -2.163   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       7.700  -2.667   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0       6.536  -1.659   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0       7.409  -4.180   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.230  -2.163   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.394  -3.171   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0      15.849  -2.667   0.000  0.00  0.00           N+1
HETATM   20  O   UNK     0      16.140  -1.155   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0      17.013  -3.675   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    6   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0256253
HETATM    1  O1  UNL     1      -2.998   1.977   2.278  1.00  0.00           O  
HETATM    2  N1  UNL     1      -1.998   2.375   1.669  1.00  0.00           N1+
HETATM    3  O2  UNL     1      -1.670   3.698   1.769  1.00  0.00           O1-
HETATM    4  O3  UNL     1      -1.248   1.543   0.928  1.00  0.00           O  
HETATM    5  C1  UNL     1      -0.337   0.585   1.402  1.00  0.00           C  
HETATM    6  C2  UNL     1       0.261  -0.104   0.194  1.00  0.00           C  
HETATM    7  C3  UNL     1      -0.887  -0.744  -0.559  1.00  0.00           C  
HETATM    8  O4  UNL     1      -0.419  -1.413  -1.709  1.00  0.00           O  
HETATM    9  N2  UNL     1      -1.327  -2.055  -2.515  1.00  0.00           N1+
HETATM   10  O5  UNL     1      -1.392  -3.291  -2.550  1.00  0.00           O  
HETATM   11  O6  UNL     1      -2.194  -1.352  -3.309  1.00  0.00           O1-
HETATM   12  C4  UNL     1       1.303  -1.110   0.556  1.00  0.00           C  
HETATM   13  O7  UNL     1       0.842  -2.146   1.374  1.00  0.00           O  
HETATM   14  N3  UNL     1       1.720  -3.113   1.758  1.00  0.00           N1+
HETATM   15  O8  UNL     1       2.010  -4.024   0.979  1.00  0.00           O  
HETATM   16  O9  UNL     1       2.276  -3.071   3.000  1.00  0.00           O1-
HETATM   17  C5  UNL     1       0.925   0.977  -0.642  1.00  0.00           C  
HETATM   18  O10 UNL     1      -0.019   1.931  -1.040  1.00  0.00           O  
HETATM   19  N4  UNL     1       0.423   2.993  -1.814  1.00  0.00           N1+
HETATM   20  O11 UNL     1       1.604   3.120  -2.175  1.00  0.00           O  
HETATM   21  O12 UNL     1      -0.494   3.946  -2.197  1.00  0.00           O1-
HETATM   22  H1  UNL     1      -0.791  -0.132   2.113  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.486   1.091   1.949  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.677  -0.006  -0.767  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.327  -1.510   0.113  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.716  -1.526  -0.378  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.116  -0.557   1.105  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.376   0.496  -1.540  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.718   1.422   0.010  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5
CONECT    5    6   22   23
CONECT    6    7   12   17
CONECT    7    8   24   25
CONECT    8    9
CONECT    9   10   10   11
CONECT   12   13   26   27
CONECT   13   14
CONECT   14   15   15   16
CONECT   17   18   28   29
CONECT   18   19
CONECT   19   20   20   21
END

HMDB0256253
     RDKit          3D
Pentaerythritol tetranitrate
 29 28  0  0  0  0  0  0  0  0999 V2000
   -2.9976    1.9772    2.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9978    2.3748    1.6685 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6701    3.6979    1.7687 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2483    1.5426    0.9276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.5850    1.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -0.1036    0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870   -0.7443   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4188   -1.4133   -1.7087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3270   -2.0549   -2.5150 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3920   -3.2912   -2.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -1.3517   -3.3094 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3034   -1.1096    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8419   -2.1465    1.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204   -3.1132    1.7580 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.0099   -4.0244    0.9787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -3.0711    2.9996 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9251    0.9772   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0194    1.9311   -1.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234    2.9926   -1.8136 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.6040    3.1203   -2.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    3.9464   -2.1967 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.7912   -0.1322    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860    1.0915    1.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773   -0.0061   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271   -1.5098    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163   -1.5257   -0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160   -0.5572    1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3760    0.4964   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185    1.4219    0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
 12 26  1  0
 12 27  1  0
 17 28  1  0
 17 29  1  0
M  CHG  8   2   1   3  -1   9   1  11  -1  14   1  16  -1  19   1  21  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Dinitrato-2,2-bis(nitratomethyl)propane	ChEBI
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitrate	ChEBI
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitrate ester	ChEBI
2,2-Bis(hydroxymethyl)-1,3-propanediol tetranitrate	ChEBI
3-(Nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate	ChEBI
Corpent	ChEBI
Neopentanetetrayl nitrate	ChEBI
Nitropenta	ChEBI
Nitropentaerythrite	ChEBI
Nitropentaerythritol	ChEBI
PENT	ChEBI
Pentaerithrityl tetranitrate	ChEBI
Pentaerithrityli tetranitras	ChEBI
Pentaerythritylium tetranitricum	ChEBI
Penthrite	ChEBI
PETN	ChEBI
TEN	ChEBI
Tetranitrate de pentaerithrityle	ChEBI
Tetranitrato de pentaeritritilo	ChEBI
Tetranitropentaerythritol	ChEBI
Pentritol tempules	Kegg
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitric acid	Generator
2,2-Bis((nitrooxy)methyl)-1,3-propanediol dinitric acid ester	Generator
2,2-Bis(hydroxymethyl)-1,3-propanediol tetranitric acid	Generator
3-(Nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitric acid	Generator
Neopentanetetrayl nitric acid	Generator
Pentaerithrityl tetranitric acid	Generator
Tetranitric acid de pentaerithrityle	Generator
Pentaerythritol tetranitric acid	Generator
Erinit	MeSH
Parke davis brand OF pentaerythritol tetranitrate	MeSH
Tetranitrate, pentaerythritol	MeSH
Alpharma brand OF pentaerythritol tetranitrate	MeSH
Dilcoran	MeSH
Nirason	MeSH
Ravensberg brand OF pentaerythritol tetranitrate	MeSH
Tetrate	MeSH
Vanguard brand OF pentaerythritol tetranitrate	MeSH
dexo Brand OF pentaerythritol tetranitrate	MeSH
Nitrodex	MeSH
Pentalog	MeSH
Peritrate	MeSH

Chemical Formula

C₅H₈N₄O₁₂

Average Molecular Weight

316.1366

Monoisotopic Molecular Weight

316.01387174

IUPAC Name

3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate

Traditional Name

pentaerythritol tetranitrate

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O

InChI Identifier

InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2

InChI Key

TZRXHJWUDPFEEY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxoanionic compounds

Sub Class

Organic nitrates

Direct Parent

Alkyl nitrates

Alternative Parents

Substituents

Alkyl nitrate
Organic nitro compound
Organic nitric acid or derivatives
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

pentaerythritol nitrate (CHEBI:25879 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0256253)
Extracellular (HMDB: HMDB0256253)

Source

Exogenous

Exogenous (HMDB: HMDB0256253)

Process

Not Available

Role

Industrial application

Manufacturing industry

Combustive element

Explosive (HMDB: HMDB0256253)

Vasodilator agent (HMDB: HMDB0256253)

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	1.62	ALOGPS
logP	0.96	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	220.2 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	58.5 m³·mol⁻¹	ChemAxon
Polarizability	22.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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]+	137.825	30932474
DeepCCS	[M-H]-	135.457	30932474
DeepCCS	[M-2H]-	168.344	30932474
DeepCCS	[M+Na]+	143.911	30932474
AllCCS	[M+H]+	161.3	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	154.1	32859911
AllCCS	[M+Na-2H]-	153.8	32859911
AllCCS	[M+HCOO]-	153.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pentaerythritol tetranitrate	[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O	2986.7	Standard polar	33892256
Pentaerythritol tetranitrate	[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O	1819.8	Standard non polar	33892256
Pentaerythritol tetranitrate	[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O	1777.3	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 - Pentaerythritol tetranitrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0009000000-9271f398a2613e45f1c4	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaerythritol tetranitrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004j-9000000000-14fe59ae096adb8f0c17	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaerythritol tetranitrate 10V, Positive-QTOF	splash10-014i-0009000000-68a44f733aacfc2a316d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaerythritol tetranitrate 20V, Positive-QTOF	splash10-014i-0009000000-185ffab1386913b39016	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaerythritol tetranitrate 40V, Positive-QTOF	splash10-066s-3039000000-22fcdf0636286b159cca	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaerythritol tetranitrate 10V, Negative-QTOF	splash10-014i-0009000000-eda307067ca65e9d68b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaerythritol tetranitrate 20V, Negative-QTOF	splash10-014i-1009000000-d1a266dd956e911a5f34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaerythritol tetranitrate 40V, Negative-QTOF	splash10-016r-8159000000-d0a1089c0acf2a27da5c	2016-08-03	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

DB06154

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6271

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pentaerythritol_tetranitrate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

25879

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 Pentaerythritol tetranitrate (HMDB0256253)

MOL for HMDB0256253 (Pentaerythritol tetranitrate)

3D MOL for HMDB0256253 (Pentaerythritol tetranitrate)

3D SDF for HMDB0256253 (Pentaerythritol tetranitrate)

3D-SDF for HMDB0256253 (Pentaerythritol tetranitrate)

PDB for HMDB0256253 (Pentaerythritol tetranitrate)

3D PDB for HMDB0256253 (Pentaerythritol tetranitrate)

SMILES for HMDB0256253 (Pentaerythritol tetranitrate)

INCHI for HMDB0256253 (Pentaerythritol tetranitrate)

Structure for HMDB0256253 (Pentaerythritol tetranitrate)

3D Structure for HMDB0256253 (Pentaerythritol tetranitrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra