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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:28:25 UTC

Update Date

2021-09-26 22:59:36 UTC

HMDB ID

HMDB0249007

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzo[e]pyrene

Description

benzo[e]pyrene, also known as 1,2-benzpyrene or b(e)p, belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Based on a literature review a significant number of articles have been published on benzo[e]pyrene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzo[e]pyrene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzo[e]pyrene 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

HMDB0249007
     RDKit          3D
Benzo[e]pyrene
 32 36  0  0  0  0  0  0  0  0999 V2000
    2.9547    2.6077    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6467    1.4348    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    0.2070    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.1855    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    1.3973    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697    2.6115    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511    1.3647   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    2.5439   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419    2.4817   -0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    1.2729   -0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899    0.0854   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1853   -1.1136   -0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -2.2531   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -2.2593   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -3.4353   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263   -3.4625    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -2.2402    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789   -1.0498    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974   -1.0405   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150    0.1472   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171    3.5304    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403    1.3860    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.7066    0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784    3.5688    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535    3.5244    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    3.4117   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724    1.2358   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762   -1.1096   -0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -3.2267   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -4.3939   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -4.4014    0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7431   -2.3044    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  1  1  0
 20  7  1  0
 18  4  1  0
 20 11  1  0
 19 14  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END


  Mrv1652304272019092D          

 20 24  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  2  0  0  0  0
  8 16  2  0  0  0  0
  9 17  2  0  0  0  0
 10 18  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 19  2  0  0  0  0
 14 20  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249007

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=C2C(=C1)C1=CC=CC3=C1C1=C(C=CC=C21)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H12/c1-2-8-16-15(7-1)17-9-3-5-13-11-12-14-6-4-10-18(16)20(14)19(13)17/h1-12H

> <INCHI_KEY>
TXVHTIQJNYSSKO-UHFFFAOYSA-N

> <FORMULA>
C20H12

> <MOLECULAR_WEIGHT>
252.3093

> <EXACT_MASS>
252.093900384

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.882541022374802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

> <ALOGPS_LOGP>
6.33

> <JCHEM_LOGP>
5.273404237333333

> <ALOGPS_LOGS>
-8.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
83.1728

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249007
     RDKit          3D
Benzo[e]pyrene
 32 36  0  0  0  0  0  0  0  0999 V2000
    2.9547    2.6077    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6467    1.4348    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    0.2070    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.1855    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    1.3973    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697    2.6115    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511    1.3647   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    2.5439   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419    2.4817   -0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    1.2729   -0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899    0.0854   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1853   -1.1136   -0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -2.2531   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -2.2593   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -3.4353   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263   -3.4625    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -2.2402    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789   -1.0498    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974   -1.0405   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150    0.1472   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171    3.5304    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403    1.3860    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.7066    0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784    3.5688    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535    3.5244    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    3.4117   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724    1.2358   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762   -1.1096   -0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -3.2267   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -4.3939   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -4.4014    0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7431   -2.3044    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  1  1  0
 20  7  1  0
 18  4  1  0
 20 11  1  0
 19 14  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.080   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.160   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.160   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.850   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    5    9                                                       
CONECT    4    6   10                                                       
CONECT    5    3   13                                                       
CONECT    6    4   14                                                       
CONECT    7    1   15                                                       
CONECT    8    2   16                                                       
CONECT    9    3   17                                                       
CONECT   10    4   18                                                       
CONECT   11   12   13                                                       
CONECT   12   11   14                                                       
CONECT   13    5   11   19                                                  
CONECT   14    6   12   20                                                  
CONECT   15    7   16   17                                                  
CONECT   16    8   15   18                                                  
CONECT   17    9   15   19                                                  
CONECT   18   10   16   20                                                  
CONECT   19   13   17   20                                                  
CONECT   20   14   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

COMPND    HMDB0249007
HETATM    1  C1  UNL     1       2.955   2.608   0.260  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.647   1.435   0.289  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.975   0.207   0.219  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.621   0.186   0.120  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.926   1.397   0.092  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.570   2.612   0.160  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.451   1.365  -0.008  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.169   2.544  -0.039  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.542   2.482  -0.140  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.188   1.273  -0.208  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.490   0.085  -0.179  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.185  -1.114  -0.250  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.438  -2.253  -0.216  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.058  -2.259  -0.117  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.341  -3.435  -0.085  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.026  -3.463   0.013  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.675  -2.240   0.081  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.979  -1.050   0.052  1.00  0.00           C  
HETATM   19  C19 UNL     1      -0.397  -1.041  -0.047  1.00  0.00           C  
HETATM   20  C20 UNL     1      -1.115   0.147  -0.078  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.517   3.530   0.317  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.740   1.386   0.367  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.571  -0.707   0.246  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.078   3.569   0.141  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.754   3.524   0.008  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.145   3.412  -0.167  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.272   1.236  -0.287  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.276  -1.110  -0.329  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.912  -3.227  -0.268  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.867  -4.394  -0.141  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.579  -4.401   0.036  1.00  0.00           H  
HETATM   32  H12 UNL     1       2.743  -2.304   0.158  1.00  0.00           H  
CONECT    1    2    2    6   21
CONECT    2    3   22
CONECT    3    4    4   23
CONECT    4    5   18
CONECT    5    6    6    7
CONECT    6   24
CONECT    7    8    8   20
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   27
CONECT   11   12   12   20
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   19
CONECT   15   16   16   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   19   20   20
END

HMDB0249007
     RDKit          3D
Benzo[e]pyrene
 32 36  0  0  0  0  0  0  0  0999 V2000
    2.9547    2.6077    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6467    1.4348    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    0.2070    0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.1855    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    1.3973    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5697    2.6115    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511    1.3647   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691    2.5439   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419    2.4817   -0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    1.2729   -0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899    0.0854   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1853   -1.1136   -0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -2.2531   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0582   -2.2593   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -3.4353   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263   -3.4625    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -2.2402    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789   -1.0498    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974   -1.0405   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150    0.1472   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171    3.5304    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403    1.3860    0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.7066    0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784    3.5688    0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535    3.5244    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    3.4117   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724    1.2358   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762   -1.1096   -0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -3.2267   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -4.3939   -0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -4.4014    0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7431   -2.3044    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6  1  1  0
 20  7  1  0
 18  4  1  0
 20 11  1  0
 19 14  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Benzopyrene	ChEBI
1,2-Benzpyrene	ChEBI
4,5-Benzopyrene	ChEBI
4,5-Benzpyrene	ChEBI
9,10-Benzpyrene	ChEBI
b(e)p	ChEBI
Benzo(e)pyrene	ChEBI
Benzo(L)pyrene	ChEBI
1,2-benzo(e)Pyrene	MeSH

Chemical Formula

C₂₀H₁₂

Average Molecular Weight

252.3093

Monoisotopic Molecular Weight

252.093900384

IUPAC Name

pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

Traditional Name

pentacyclo[10.6.2.0^{2,7}.0^{8,20}.0^{15,19}]icosa-1(18),2,4,6,8,10,12(20),13,15(19),16-decaene

CAS Registry Number

Not Available

SMILES

C1=CC=C2C(=C1)C1=CC=CC3=C1C1=C(C=CC=C21)C=C3

InChI Identifier

InChI=1S/C20H12/c1-2-8-16-15(7-1)17-9-3-5-13-11-12-14-6-4-10-18(16)20(14)19(13)17/h1-12H

InChI Key

TXVHTIQJNYSSKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzo-e-pyrene
Triphenylene
Phenanthrene
Anthracene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

ortho- and peri-fused polycyclic arene (CHEBI:34567 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0249007)

Process

Not Available

Role

Biological role

carcinogenic agent (HMDB: HMDB0249007)
mutagen (HMDB: HMDB0249007)

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	6.33	ALOGPS
logP	5.27	ChemAxon
logS	-8.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.17 m³·mol⁻¹	ChemAxon
Polarizability	28.88 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	197.462	30932474
DeepCCS	[M+Na]+	172.611	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	153.8	32859911
AllCCS	[M+NH4]+	161.3	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	163.4	32859911
AllCCS	[M+Na-2H]-	161.7	32859911
AllCCS	[M+HCOO]-	159.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzo[e]pyrene	C1=CC=C2C(=C1)C1=CC=CC3=C1C1=C(C=CC=C21)C=C3	4008.6	Standard polar	33892256
Benzo[e]pyrene	C1=CC=C2C(=C1)C1=CC=CC3=C1C1=C(C=CC=C21)C=C3	2761.9	Standard non polar	33892256
Benzo[e]pyrene	C1=CC=C2C(=C1)C1=CC=CC3=C1C1=C(C=CC=C21)C=C3	2774.1	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 - Benzo[e]pyrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0090000000-773e0a0b35caced0dc1f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[e]pyrene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-0290000000-f2a420df6056d1b95011	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 - Benzo[e]pyrene 10V, Positive-QTOF	splash10-0udi-0090000000-1984c6587d2f2d083b5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 20V, Positive-QTOF	splash10-0udi-0090000000-84c643624305c0ba2c7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 40V, Positive-QTOF	splash10-0ufr-0090000000-16b581d885a86d621255	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 10V, Negative-QTOF	splash10-0udi-0090000000-4c4c5b8f68955b2dd585	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 20V, Negative-QTOF	splash10-0udi-0090000000-4c4c5b8f68955b2dd585	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 40V, Negative-QTOF	splash10-0udi-0090000000-e5765caa2972a81c9af6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 10V, Positive-QTOF	splash10-0udi-0090000000-b5f9e841f69a96c6392a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 20V, Positive-QTOF	splash10-0udi-0090000000-b5f9e841f69a96c6392a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 40V, Positive-QTOF	splash10-0udi-0090000000-09db28c30dce749384e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 10V, Negative-QTOF	splash10-0udi-0090000000-969da6c938a324fffb4f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 20V, Negative-QTOF	splash10-0udi-0090000000-969da6c938a324fffb4f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[e]pyrene 40V, Negative-QTOF	splash10-0udi-0090000000-969da6c938a324fffb4f	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

8774

KEGG Compound ID

C14435

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzo(e)pyrene

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

34567

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 Benzo[e]pyrene (HMDB0249007)

MOL for HMDB0249007 (Benzo[e]pyrene)

3D MOL for HMDB0249007 (Benzo[e]pyrene)

3D SDF for HMDB0249007 (Benzo[e]pyrene)

3D-SDF for HMDB0249007 (Benzo[e]pyrene)

PDB for HMDB0249007 (Benzo[e]pyrene)

3D PDB for HMDB0249007 (Benzo[e]pyrene)

SMILES for HMDB0249007 (Benzo[e]pyrene)

INCHI for HMDB0249007 (Benzo[e]pyrene)

Structure for HMDB0249007 (Benzo[e]pyrene)

3D Structure for HMDB0249007 (Benzo[e]pyrene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra