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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 01:52:11 UTC

Update Date

2021-09-14 15:17:01 UTC

HMDB ID

HMDB0062470

Secondary Accession Numbers

HMDB62470

Metabolite Identification

Common Name

Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide

Description

Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide, also known as BPDE or benzo(a)Pyrene diol epoxide, is classified as a member of the Pyrenes. Pyrenes are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system. Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide is considered to be practically insoluble (in water) and relatively neutral. It is a carcinogenic metabolite of benzo[a]pyrene (BaP) which forms adducts with DNA and proteins and is hydrolysed to BPDE tetrols. It is used as a marker for BaP exposure (a surrogate marker for PAHs).

Structure

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

HMDB0247122
     RDKit          3D
Bpde-I
 37 42  0  0  0  0  0  0  0  0999 V2000
   -3.6401    0.9513    1.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    0.7815    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.5979    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.6891    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    1.5687    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926    2.6911    0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611    2.5420    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788    1.2596    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    1.0520   -0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993   -0.2251   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016   -1.3442    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -1.1467    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -2.2575    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -2.0652    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.8189    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994   -0.6665    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -1.8848    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538   -2.2847   -0.9562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5349   -1.7101   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0719   -0.3503   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085   -0.1834   -1.6483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978    0.2952    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777    0.1377    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298    1.7738    1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488    1.7117   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    2.7001    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7831    3.6877    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314    3.4031    0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1165    1.9083   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0811   -0.3836   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5960   -2.3447    0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641   -3.2533    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0560   -2.9632    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396   -2.6453    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2443   -2.4830    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970   -0.2802    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9874    0.5400   -1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  2  0
 20  2  1  0
 16  3  1  0
 19 17  1  0
 22  5  1  0
 23  8  1  0
 23 12  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv0541 09071422392D          

 23 28  0  0  0  0            999 V2000
   -0.7526    1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6690    2.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836    0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    3.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9198    3.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3380    0.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906    1.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3414    3.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0836    2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690    1.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888    3.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742    1.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0104    3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7526    1.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052    2.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9268    2.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630    3.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4320    2.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958    1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3484    2.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466    4.1605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846    3.1949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647    1.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
  9  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  3  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062470

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O3/c21-17-13-8-11-5-4-9-2-1-3-10-6-7-12(15(11)14(9)10)16(13)19-20(23-19)18(17)22/h1-8,17-22H

> <INCHI_KEY>
DQEPMTIXHXSFOR-UHFFFAOYSA-N

> <FORMULA>
C20H14O3

> <MOLECULAR_WEIGHT>
302.3234

> <EXACT_MASS>
302.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.18153943903202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-oxahexacyclo[11.6.2.0²,⁸.0³,⁵.0¹⁰,²⁰.0¹⁷,²¹]henicosa-1(20),2(8),9,11,13(21),14,16,18-octaene-6,7-diol

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.598270831

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.274754816600197

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.80096643042003

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5639126178284393

> <JCHEM_POLAR_SURFACE_AREA>
52.99

> <JCHEM_REFRACTIVITY>
86.14069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzo(a)pyrene diol epoxide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247122
     RDKit          3D
Bpde-I
 37 42  0  0  0  0  0  0  0  0999 V2000
   -3.6401    0.9513    1.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    0.7815    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.5979    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.6891    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    1.5687    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926    2.6911    0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611    2.5420    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788    1.2596    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    1.0520   -0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993   -0.2251   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016   -1.3442    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -1.1467    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -2.2575    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -2.0652    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.8189    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994   -0.6665    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -1.8848    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538   -2.2847   -0.9562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5349   -1.7101   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0719   -0.3503   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085   -0.1834   -1.6483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978    0.2952    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777    0.1377    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298    1.7738    1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488    1.7117   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    2.7001    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7831    3.6877    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314    3.4031    0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1165    1.9083   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0811   -0.3836   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5960   -2.3447    0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641   -3.2533    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0560   -2.9632    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396   -2.6453    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2443   -2.4830    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970   -0.2802    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9874    0.5400   -1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  2  0
 20  2  1  0
 16  3  1  0
 19 17  1  0
 22  5  1  0
 23  8  1  0
 23 12  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 07-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-14         0                                  
HETATM    1  C   UNK     0      -1.405   2.449   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.249   3.981   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.156   1.548   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.312   6.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.717   6.775   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.498   1.278   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.902   1.908   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.371   6.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.156   4.612   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.249   2.179   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.966   5.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.058   3.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.619   5.603   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.405   3.711   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.810   4.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.463   4.071   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.024   6.234   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.273   5.333   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.712   3.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.117   3.801   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.180   7.766   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.678   5.964   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.961   2.269   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    9                                                       
CONECT    3    1   10                                                       
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    7   10                                                       
CONECT    7    6   12                                                       
CONECT    8   11   13                                                       
CONECT    9    2    4   14                                                  
CONECT   10    3    6   14                                                  
CONECT   11    5    8   15                                                  
CONECT   12    7   15   16                                                  
CONECT   13    8   16   17                                                  
CONECT   14    9   10   15                                                  
CONECT   15   11   12   14                                                  
CONECT   16   12   13   19                                                  
CONECT   17   13   18   21                                                  
CONECT   18   17   20   22                                                  
CONECT   19   16   20   23                                                  
CONECT   20   18   19   23                                                  
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   56    0
END

COMPND    HMDB0247122
HETATM    1  O1  UNL     1      -3.640   0.951   1.631  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.275   0.781   0.275  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.829   0.598   0.223  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.003   1.689   0.181  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.387   1.569   0.131  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.193   2.691   0.090  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.561   2.542   0.040  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.079   1.260   0.033  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.453   1.052  -0.017  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.999  -0.225  -0.025  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.202  -1.344   0.015  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.834  -1.147   0.065  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.031  -2.257   0.105  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.655  -2.065   0.155  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.088  -0.819   0.165  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.299  -0.666   0.215  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.140  -1.885   0.258  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.654  -2.285  -0.956  1.00  0.00           O  
HETATM   19  C17 UNL     1      -3.535  -1.710  -0.025  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.072  -0.350  -0.275  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.308  -0.183  -1.648  1.00  0.00           O  
HETATM   22  C19 UNL     1       0.898   0.295   0.124  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.278   0.138   0.073  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.130   1.774   1.921  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.549   1.712  -0.294  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.383   2.700   0.186  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.783   3.688   0.096  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.231   3.403   0.006  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.117   1.908  -0.050  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.081  -0.384  -0.064  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.596  -2.345   0.010  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.464  -3.253   0.099  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.056  -2.963   0.186  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.840  -2.645   1.011  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.244  -2.483   0.394  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.097  -0.280   0.198  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.987   0.540  -1.734  1.00  0.00           H  
CONECT    1    2   24
CONECT    2    3   20   25
CONECT    3    4    4   16
CONECT    4    5   26
CONECT    5    6    6   22
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   23
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   13   23
CONECT   13   14   14   32
CONECT   14   15   33
CONECT   15   16   16   22
CONECT   16   17
CONECT   17   18   19   34
CONECT   18   19
CONECT   19   20   35
CONECT   20   21   36
CONECT   21   37
CONECT   22   23   23
END

HMDB0247122
     RDKit          3D
Bpde-I
 37 42  0  0  0  0  0  0  0  0999 V2000
   -3.6401    0.9513    1.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    0.7815    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.5979    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    1.6891    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    1.5687    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926    2.6911    0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611    2.5420    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788    1.2596    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    1.0520   -0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993   -0.2251   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016   -1.3442    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344   -1.1467    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -2.2575    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -2.0652    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878   -0.8189    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994   -0.6665    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400   -1.8848    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538   -2.2847   -0.9562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5349   -1.7101   -0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0719   -0.3503   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3085   -0.1834   -1.6483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978    0.2952    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777    0.1377    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298    1.7738    1.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488    1.7117   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    2.7001    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7831    3.6877    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314    3.4031    0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1165    1.9083   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0811   -0.3836   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5960   -2.3447    0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641   -3.2533    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0560   -2.9632    0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396   -2.6453    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2443   -2.4830    0.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0970   -0.2802    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9874    0.5400   -1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  2  0
 20  2  1  0
 16  3  1  0
 19 17  1  0
 22  5  1  0
 23  8  1  0
 23 12  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,8-Dihydro-7,8-dihydroxybenzo[a]pyrene 9,10-oxide	ChEBI
Benzo(a)pyrene diol epoxide	ChEBI
Benzo(a)pyrene diolepoxide I	ChEBI
BP 7,8-Diol-9,10-epoxide 2	ChEBI
BPDE	ChEBI
7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene	HMDB
Anti bapde	HMDB
Benzo(a)pyrene 7,8-dihydrodiol 9,10-epoxide	HMDB
Benzo(a)pyrene-7,8-diol 9,10-epoxide	HMDB
7,8-BaP-9,10-diol epoxide	HMDB
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide	HMDB
Anti-bapde	HMDB
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide	ChEBI

Chemical Formula

C₂₀H₁₄O₃

Average Molecular Weight

302.3234

Monoisotopic Molecular Weight

302.094294314

IUPAC Name

4-oxahexacyclo[11.6.2.0²,⁸.0³,⁵.0¹⁰,²⁰.0¹⁷,²¹]henicosa-1(20),2(8),9,11,13(21),14,16,18-octaene-6,7-diol

Traditional Name

benzo(a)pyrene diol epoxide

CAS Registry Number

58917-67-2

SMILES

OC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O

InChI Identifier

InChI=1S/C20H14O3/c21-17-13-8-11-5-4-9-2-1-3-10-6-7-12(15(11)14(9)10)16(13)19-20(23-19)18(17)22/h1-8,17-22H

InChI Key

DQEPMTIXHXSFOR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrenes. Pyrenes are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Pyrenes

Sub Class

Not Available

Direct Parent

Pyrenes

Alternative Parents

Substituents

Pyrene
Phenanthrol
Phenanthrene
Naphthalene
Tetralin
Secondary alcohol
1,2-diol
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:30614 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.019 g/l	ALOGPS
LogP	2.83	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.83	ALOGPS
logP	2.6	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.14 m³·mol⁻¹	ChemAxon
Polarizability	32.18 Å³	ChemAxon
Number of Rings	6	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
DarkChem	[M+H]+	168.659	31661259
DarkChem	[M-H]-	166.381	31661259
DeepCCS	[M-2H]-	208.338	30932474
DeepCCS	[M+Na]+	183.555	30932474
AllCCS	[M+H]+	173.9	32859911
AllCCS	[M+H-H2O]+	170.5	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.9	32859911
AllCCS	[M-H]-	178.9	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	176.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide	OC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O	4433.8	Standard polar	33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide	OC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O	2869.4	Standard non polar	33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide	OC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O	3342.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TMS,isomer #1	C[Si](C)(C)OC1C(O)C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC21)C3=C45	3167.6	Semi standard non polar	33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TMS,isomer #2	C[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O)C3=C45	3199.9	Semi standard non polar	33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,2TMS,isomer #1	C[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O[Si](C)(C)C)C3=C45	3182.9	Semi standard non polar	33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(O)C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC21)C3=C45	3416.3	Semi standard non polar	33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O)C3=C45	3428.0	Semi standard non polar	33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O[Si](C)(C)C(C)(C)C)C3=C45	3595.5	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[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-0090000000-152c9cf2a50947f26f2c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (2 TMS) - 70eV, Positive	splash10-0kmr-7019100000-f7da140ee19b3f0897b3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 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 - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Positive-QTOF	splash10-0udi-0019000000-282dfb81066da2878f73	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Positive-QTOF	splash10-0udi-2089000000-db5f1c46ceefa9333139	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Positive-QTOF	splash10-05n0-1090000000-17807b407c1cd92e90ce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Negative-QTOF	splash10-0udi-0009000000-3cebeaad6380d7f45ed8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Negative-QTOF	splash10-0udi-0049000000-ad94deb86b0fab35aece	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Negative-QTOF	splash10-0ufr-1090000000-efc7a183027b49eec6c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Negative-QTOF	splash10-0udi-0009000000-e692d58cc60b5b612091	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Negative-QTOF	splash10-0udi-0049000000-5ef0b27e7167c9cca44d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Negative-QTOF	splash10-0f7o-1091000000-684f758a5ace9d370546	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Positive-QTOF	splash10-0udi-0049000000-649fbd314baf527362aa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Positive-QTOF	splash10-0udr-0098000000-679c99bf1e7d577c4889	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Positive-QTOF	splash10-0udr-1094000000-c9b1ce91e6e2f4a272da	2021-09-25	Wishart Lab	View Spectrum

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

37707

KEGG Compound ID

C14853

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

41322

PDB ID

Not Available

ChEBI ID

30614

Food Biomarker Ontology

Not Available

VMH ID

M01376

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-7,8-dihydrodiol-9,10-oxide (HMDB0062470)

MOL for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

3D MOL for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

3D SDF for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

3D-SDF for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

PDB for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

3D PDB for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

SMILES for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

INCHI for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

Structure for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

3D Structure for HMDB0062470 (Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra