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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 01:51:42 UTC

Update Date

2019-07-23 07:18:36 UTC

HMDB ID

HMDB0062469

Secondary Accession Numbers

HMDB62469

Metabolite Identification

Common Name

Benzo[a]pyrene

Description

Benzo[a]pyrene, also known as 3,4-Benzopyrene or 3,4-BP, is classified as a member of the Benzopyrenes. Benzopyrenes are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Benzo[a]pyrene is formally rated as a carcinogenic (IARC 1) potentially toxic compound. Benzo[a]pyrene is a crystalline, aromatic hydrocarbon consisting of five fused benzene rings and formed during the incomplete combustion of organic matter. Benzo[a]pyrene is primarily found in gasoline and diesel exhaust, cigarette smoke, coal tar and coal tar pitch, charcoal-broiled foods and certain other foods, amino acids, fatty acids and carbohydrate pyrolysis products, soot smoke, creosote oil, petroleum asphalt and shale oils. This substance is used only for research purposes. Benzo[a]pyrene is reasonably anticipated to be a human carcinogen (NCI05). Its diol epoxide metabolites (more commonly known as BPDE) react and bind to DNA, resulting in mutations and eventually cancer. It is listed as a Group 1 carcinogen by the IARC. In the 18th century a scrotal cancer of chimney sweepers, the chimney sweeps' carcinoma, was already connected to soot. [Wikipedia ]

Structure

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

HMDB0062469
     RDKit          3D
Benzo[a]pyrene
 32 36  0  0  0  0  0  0  0  0999 V2000
    4.5740    0.8781    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -0.4869    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.0272    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -0.1790    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    1.2100   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4946    1.7270    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    2.0570   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    1.5584   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2383    2.4037   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5322    1.9311   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.5759   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    0.0477   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2578   -1.2900   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -2.1430   -0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052   -1.6217   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -2.4674    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707   -1.9869    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -0.6491    0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    0.2080   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -0.2703   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5697    1.2932    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1965   -1.1659    0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9884   -2.0595    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618    2.7902   -0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    3.1127   -0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925    3.4711   -0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    2.5849   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8858    0.7192   -0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507   -1.7419   -0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561   -3.2289   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0416   -3.5412    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111   -2.7096    0.1854 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
 19  8  1  0
 18  4  1  0
 20 11  1  0
 20 15  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 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
   -4.5375    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
   -4.1250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    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
   -2.8875    2.1434    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
   -2.0625   -0.7144    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
   -3.3000    1.4290    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
   -1.6500    1.4290    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
   -1.6500    0.0000    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
   -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  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4 15  2  0  0  0  0
  5 13  2  0  0  0  0
  6 14  1  0  0  0  0
  7 17  2  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  2  0  0  0  0
 11 18  2  0  0  0  0
 12 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 19  1  0  0  0  0
 14 19  1  0  0  0  0
 15 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062469

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=C2C(=C1)C=C1C=CC3=CC=CC4=CC=C2C1=C34

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

> <INCHI_KEY>
FMMWHPNWAFZXNH-UHFFFAOYSA-N

> <FORMULA>
C20H12

> <MOLECULAR_WEIGHT>
252.3093

> <EXACT_MASS>
252.093900384

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
29.091364774905173

> <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^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene

> <ALOGPS_LOGP>
6.39

> <JCHEM_LOGP>
5.273404237333333

> <ALOGPS_LOGS>
-8.31

> <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>
1.25e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0062469
     RDKit          3D
Benzo[a]pyrene
 32 36  0  0  0  0  0  0  0  0999 V2000
    4.5740    0.8781    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -0.4869    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.0272    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -0.1790    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    1.2100   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4946    1.7270    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    2.0570   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    1.5584   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2383    2.4037   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5322    1.9311   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.5759   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    0.0477   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2578   -1.2900   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -2.1430   -0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052   -1.6217   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -2.4674    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707   -1.9869    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -0.6491    0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    0.2080   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -0.2703   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5697    1.2932    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1965   -1.1659    0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9884   -2.0595    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618    2.7902   -0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    3.1127   -0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925    3.4711   -0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    2.5849   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8858    0.7192   -0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507   -1.7419   -0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561   -3.2289   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0416   -3.5412    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111   -2.7096    0.1854 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
 19  8  1  0
 18  4  1  0
 20 11  1  0
 20 15  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 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      -8.470   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.700   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.700   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      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.850   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.160   2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.160   0.000   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      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.540   0.000   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      -5.390   1.334   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    4                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    1   15                                                       
CONECT    5    3   13                                                       
CONECT    6    3   14                                                       
CONECT    7    2   17                                                       
CONECT    8    9   13                                                       
CONECT    9    8   16                                                       
CONECT   10   11   14                                                       
CONECT   11   10   18                                                       
CONECT   12   15   16                                                       
CONECT   13    5    8   19                                                  
CONECT   14    6   10   19                                                  
CONECT   15    4   12   17                                                  
CONECT   16    9   12   20                                                  
CONECT   17    7   15   18                                                  
CONECT   18   11   17   20                                                  
CONECT   19   13   14   20                                                  
CONECT   20   16   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

COMPND    HMDB0062469
HETATM    1  C1  UNL     1       4.574   0.878   0.117  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.361  -0.487   0.200  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.088  -1.027   0.169  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.010  -0.179   0.053  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.212   1.210  -0.032  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.495   1.727   0.001  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.133   2.057  -0.148  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.150   1.558  -0.182  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.238   2.404  -0.298  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.532   1.931  -0.335  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.770   0.576  -0.254  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.047   0.048  -0.285  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.258  -1.290  -0.204  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.191  -2.143  -0.088  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.905  -1.622  -0.056  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.849  -2.467   0.059  1.00  0.00           C  
HETATM   17  C17 UNL     1       0.471  -1.987   0.096  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.725  -0.649   0.017  1.00  0.00           C  
HETATM   19  C19 UNL     1      -0.378   0.208  -0.101  1.00  0.00           C  
HETATM   20  C20 UNL     1      -1.684  -0.270  -0.137  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.570   1.293   0.141  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.197  -1.166   0.291  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.988  -2.060   0.235  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.662   2.790  -0.064  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.322   3.113  -0.211  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.093   3.471  -0.364  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.387   2.585  -0.425  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.886   0.719  -0.376  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.251  -1.742  -0.226  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.356  -3.229  -0.022  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.042  -3.541   0.123  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.211  -2.710   0.185  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   25
CONECT    8    9   19
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   30
CONECT   15   16   16   20
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   19   20   20
END

HMDB0062469
     RDKit          3D
Benzo[a]pyrene
 32 36  0  0  0  0  0  0  0  0999 V2000
    4.5740    0.8781    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -0.4869    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.0272    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -0.1790    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    1.2100   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4946    1.7270    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    2.0570   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    1.5584   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2383    2.4037   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5322    1.9311   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.5759   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    0.0477   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2578   -1.2900   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -2.1430   -0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052   -1.6217   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8486   -2.4674    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707   -1.9869    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -0.6491    0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    0.2080   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -0.2703   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5697    1.2932    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1965   -1.1659    0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9884   -2.0595    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618    2.7902   -0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    3.1127   -0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925    3.4711   -0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    2.5849   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8858    0.7192   -0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507   -1.7419   -0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561   -3.2289   -0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0416   -3.5412    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111   -2.7096    0.1854 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
 19  8  1  0
 18  4  1  0
 20 11  1  0
 20 15  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(b(a)p)	ChEBI
3,4-Benzopyrene	ChEBI
3,4-Benzpyrene	ChEBI
3,4-BP	ChEBI
Benzo(a)pyrene	ChEBI
Benzo[def]chrysene	ChEBI
Benzpyrene	ChEBI
BP	ChEBI
3,4 Benzpyrene	HMDB
3,4 Benzopyrene	HMDB

Chemical Formula

C₂₀H₁₂

Average Molecular Weight

252.3093

Monoisotopic Molecular Weight

252.093900384

IUPAC Name

pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene

Traditional Name

pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene

CAS Registry Number

50-32-8

SMILES

C1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3

InChI Identifier

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

InChI Key

FMMWHPNWAFZXNH-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-a-pyrene
Chrysene
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:29865 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0062469)

Source

Exogenous

Exogenous (HMDB: HMDB0062469)

Process

Not Available

Role

Biological role

Carcinogenic agent (HMDB: HMDB0062469)

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	1.2e-06 g/l	ALOGPS
LogP	6.39	ALOGPS

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	152.046	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002037

Predicted Molecular Properties

Property	Value	Source
logP	6.39	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	29.09 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
DarkChem	[M+H]+	155.245	31661259
DarkChem	[M-H]-	157.755	31661259
DeepCCS	[M-2H]-	202.781	30932474
DeepCCS	[M+Na]+	177.904	30932474
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	161.4	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.	7.68 minutes	32390414
Predicted by Siyang on May 30, 2022	26.5208 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3313.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1037.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	406.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	699.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	715.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1181.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1444.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	140.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2092.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	981.5 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	2710.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	783.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	829.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1100.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	605.3 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	106.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzo[a]pyrene	C1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3	4071.5	Standard polar	33892256
Benzo[a]pyrene	C1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3	2798.7	Standard non polar	33892256
Benzo[a]pyrene	C1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3	2805.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)	splash10-0udi-0590000000-6a1e4169eaee2450b6aa	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)	splash10-0udi-0390000000-d87401bcab72c45a1d87	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzo[a]pyrene CI-B (Non-derivatized)	splash10-0udi-0090000000-aebdc23a6e4cb494681e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)	splash10-0udi-0590000000-6a1e4169eaee2450b6aa	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)	splash10-0udi-0390000000-d87401bcab72c45a1d87	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzo[a]pyrene CI-B (Non-derivatized)	splash10-0udi-0090000000-aebdc23a6e4cb494681e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0090000000-4ed81317d745f20ae6d3	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-0290000000-21f41e03667be1e6edca	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[a]pyrene 10V, Positive-QTOF	splash10-0udi-0090000000-f612ac63f25ab09a3fb7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Positive-QTOF	splash10-0udi-0090000000-da5273239d688cd66f49	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Positive-QTOF	splash10-0ufr-0090000000-fb6dcdd11a97e4d74479	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 10V, Negative-QTOF	splash10-0udi-0090000000-31f8cde7b8fb38348ad0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Negative-QTOF	splash10-0udi-0090000000-31f8cde7b8fb38348ad0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Negative-QTOF	splash10-0udi-0090000000-f5fc2a06e6c04b87e62f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 10V, Negative-QTOF	splash10-0udi-0090000000-969da6c938a324fffb4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Negative-QTOF	splash10-0udi-0090000000-969da6c938a324fffb4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Negative-QTOF	splash10-0udi-0090000000-969da6c938a324fffb4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 10V, Positive-QTOF	splash10-0udi-0090000000-b5f9e841f69a96c6392a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Positive-QTOF	splash10-0udi-0090000000-b5f9e841f69a96c6392a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Positive-QTOF	splash10-0udi-0090000000-d38a61935d2a229c0c1f	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KEGG Compound ID

C07535

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzo(a)pyrene

METLIN ID

Not Available

PubChem Compound

2336

PDB ID

Not Available

ChEBI ID

29865

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 Benzo[a]pyrene (HMDB0062469)

MOL for HMDB0062469 (Benzo[a]pyrene)

3D MOL for HMDB0062469 (Benzo[a]pyrene)

3D SDF for HMDB0062469 (Benzo[a]pyrene)

3D-SDF for HMDB0062469 (Benzo[a]pyrene)

PDB for HMDB0062469 (Benzo[a]pyrene)

3D PDB for HMDB0062469 (Benzo[a]pyrene)

SMILES for HMDB0062469 (Benzo[a]pyrene)

INCHI for HMDB0062469 (Benzo[a]pyrene)

Structure for HMDB0062469 (Benzo[a]pyrene)

3D Structure for HMDB0062469 (Benzo[a]pyrene)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra