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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:20:55 UTC

Update Date

2022-03-07 03:17:44 UTC

HMDB ID

HMDB0060439

Secondary Accession Numbers

HMDB60439

Metabolite Identification

Common Name

Benzo[a]pyrene-7,8-oxide

Description

Benzo[a]pyrene-7,8-oxide 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. Benzo[a]pyrene-7,8-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060439
     RDKit          3D
Benzo[a]pyrene-7,8-oxide
 33 38  0  0  0  0  0  0  0  0999 V2000
    2.7647    1.5945   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812    1.3594   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943   -0.0131   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -0.6800    1.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6880   -1.0791    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373   -0.7680    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243   -1.7966    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0365   -1.5395    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9258   -2.5896    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931   -2.3149    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750   -1.0230    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -0.7724    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6013    0.5252   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    1.5616   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    1.2833   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    2.2945   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253    2.0510   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4447    0.7692   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    0.5176   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4864   -0.2432    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.0007    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925    2.6249   -0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    2.1751   -0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6256   -0.1989   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -2.0932   -0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342   -2.8268    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5503   -3.5803    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919   -3.1442    0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8078   -1.6156    0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644    0.7244   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0660    2.5695   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    3.3215   -0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242    2.9060   -0.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 19  1  1  0
  5  3  1  0
 19  6  1  0
 20  8  1  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
M  END


  Mrv0541 05161318202D          

 21 26  0  0  0  0            999 V2000
   -0.8239    1.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494    2.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    0.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    3.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5728    3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    0.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7226    0.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3704    0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1942    0.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8461    2.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745    2.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4494    0.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222    2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210    1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971    1.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2955    1.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5687    1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239    1.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477    1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1193    1.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    1.9095    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  8  2  0  0  0  0
 11  2  1  0  0  0  0
 11  4  1  0  0  0  0
 12  3  2  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 17  1  0  0  0  0
 21 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060439

> <DATABASE_NAME>
hmdb

> <SMILES>
O1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O/c1-2-11-4-5-13-10-16-14(8-9-17-20(16)21-17)15-7-6-12(3-1)18(11)19(13)15/h1-10,17,20H

> <INCHI_KEY>
OLLMQFHYRYHKTD-UHFFFAOYSA-N

> <FORMULA>
C20H12O

> <MOLECULAR_WEIGHT>
268.3087

> <EXACT_MASS>
268.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
29.820367618769758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-oxahexacyclo[11.6.2.0²,⁸.0⁵,⁷.0¹⁰,²⁰.0¹⁷,²¹]henicosa-1,3,8,10(20),11,13(21),14,16,18-nonaene

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
4.468856388333333

> <ALOGPS_LOGS>
-7.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.267014407725655

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
84.53429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzo(a)pyrene 7,8-oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060439
     RDKit          3D
Benzo[a]pyrene-7,8-oxide
 33 38  0  0  0  0  0  0  0  0999 V2000
    2.7647    1.5945   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812    1.3594   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943   -0.0131   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -0.6800    1.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6880   -1.0791    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373   -0.7680    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243   -1.7966    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0365   -1.5395    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9258   -2.5896    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931   -2.3149    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750   -1.0230    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -0.7724    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6013    0.5252   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    1.5616   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    1.2833   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    2.2945   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253    2.0510   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4447    0.7692   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    0.5176   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4864   -0.2432    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.0007    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925    2.6249   -0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    2.1751   -0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6256   -0.1989   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -2.0932   -0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342   -2.8268    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5503   -3.5803    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919   -3.1442    0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8078   -1.6156    0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644    0.7244   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0660    2.5695   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    3.3215   -0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242    2.9060   -0.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 19  1  1  0
  5  3  1  0
 19  6  1  0
 20  8  1  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.538   2.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.839   4.372   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.699   1.708   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.398   5.824   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.936   5.905   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.678   0.497   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.216   0.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.291   0.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.829   0.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.313   4.694   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.699   4.452   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.839   1.788   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.775   4.614   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.453   2.031   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.915   1.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.152   3.403   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.528   2.192   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.538   3.161   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.076   3.241   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.689   3.484   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.227   3.564   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1   11                                                       
CONECT    3    1   12                                                       
CONECT    4    5   11                                                       
CONECT    5    4   13                                                       
CONECT    6    7   12                                                       
CONECT    7    6   15                                                       
CONECT    8    9   14                                                       
CONECT    9    8   17                                                       
CONECT   10   13   16                                                       
CONECT   11    2    4   18                                                  
CONECT   12    3    6   18                                                  
CONECT   13    5   10   19                                                  
CONECT   14    8   15   16                                                  
CONECT   15    7   14   19                                                  
CONECT   16   10   14   20                                                  
CONECT   17    9   20   21                                                  
CONECT   18   11   12   19                                                  
CONECT   19   13   15   18                                                  
CONECT   20   16   17   21                                                  
CONECT   21   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   52    0
END

COMPND    HMDB0060439
HETATM    1  C1  UNL     1       2.765   1.594  -0.160  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.081   1.359  -0.149  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.594  -0.013  -0.037  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.346  -0.680   1.219  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.688  -1.079   0.060  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.237  -0.768   0.042  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.324  -1.797   0.133  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.036  -1.540   0.120  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.926  -2.590   0.213  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.293  -2.315   0.199  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.775  -1.023   0.094  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.142  -0.772   0.081  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.601   0.525  -0.025  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.687   1.562  -0.117  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.335   1.283  -0.102  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.408   2.295  -0.192  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.025   2.051  -0.180  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.445   0.769  -0.076  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.803   0.518  -0.063  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.486  -0.243   0.014  1.00  0.00           C  
HETATM   21  C20 UNL     1      -1.839   0.001   0.002  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.493   2.625  -0.244  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.787   2.175  -0.222  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.626  -0.199  -0.437  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.935  -2.093  -0.344  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.634  -2.827   0.218  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.550  -3.580   0.294  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.992  -3.144   0.272  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.808  -1.616   0.155  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.664   0.724  -0.035  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.066   2.569  -0.199  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.747   3.321  -0.276  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.624   2.906  -0.256  1.00  0.00           H  
CONECT    1    2    2   19   22
CONECT    2    3   23
CONECT    3    4    5   24
CONECT    4    5
CONECT    5    6   25
CONECT    6    7    7   19
CONECT    7    8   26
CONECT    8    9    9   20
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   21
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   21
CONECT   16   17   17   32
CONECT   17   18   33
CONECT   18   19   19   20
CONECT   20   21   21
END

HMDB0060439
     RDKit          3D
Benzo[a]pyrene-7,8-oxide
 33 38  0  0  0  0  0  0  0  0999 V2000
    2.7647    1.5945   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0812    1.3594   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943   -0.0131   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457   -0.6800    1.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6880   -1.0791    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373   -0.7680    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243   -1.7966    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0365   -1.5395    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9258   -2.5896    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931   -2.3149    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7750   -1.0230    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -0.7724    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6013    0.5252   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    1.5616   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    1.2833   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4080    2.2945   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253    2.0510   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4447    0.7692   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    0.5176   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4864   -0.2432    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.0007    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925    2.6249   -0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    2.1751   -0.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6256   -0.1989   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -2.0932   -0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342   -2.8268    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5503   -3.5803    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919   -3.1442    0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8078   -1.6156    0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644    0.7244   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0660    2.5695   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    3.3215   -0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242    2.9060   -0.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 19  1  1  0
  5  3  1  0
 19  6  1  0
 20  8  1  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzo[a]pyrene-7,8-epoxide	Kegg
Benzo(a)pyrene 7,8-oxide	HMDB
Benzo(a)pyrene 7,8-oxide, (+-)-isomer	HMDB
Benzo(a)pyrene 7,8-oxide, (6BS)-isomer	HMDB
Benzo(a)pyrene 7,8-epoxide	HMDB
Benzo(a)pyrene 7,8-oxide, (6BR)-isomer	HMDB

Chemical Formula

C₂₀H₁₂O

Average Molecular Weight

268.3087

Monoisotopic Molecular Weight

268.088815006

IUPAC Name

6-oxahexacyclo[11.6.2.0²,⁸.0⁵,⁷.0¹⁰,²⁰.0¹⁷,²¹]henicosa-1,3,8,10(20),11,13(21),14,16,18-nonaene

Traditional Name

benzo(a)pyrene 7,8-oxide

CAS Registry Number

Not Available

SMILES

O1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C12

InChI Identifier

InChI=1S/C20H12O/c1-2-11-4-5-13-10-16-14(8-9-17-20(16)21-17)15-7-6-12(3-1)18(11)19(13)15/h1-10,17,20H

InChI Key

OLLMQFHYRYHKTD-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
Phenanthrene
Naphthalene
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyrenes (CHEBI:34563 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060439)

Source

Exogenous

Exogenous (HMDB: HMDB0060439)

Process

Not Available

Role

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.2e-05 g/L	ALOGPS
logP	5.19	ALOGPS
logP	4.47	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.53 m³·mol⁻¹	ChemAxon
Polarizability	29.82 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	157.282	31661259
DarkChem	[M-H]-	161.816	31661259
DeepCCS	[M-2H]-	205.401	30932474
DeepCCS	[M+Na]+	180.628	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.2	32859911
AllCCS	[M+NH4]+	168.4	32859911
AllCCS	[M+Na]+	169.4	32859911
AllCCS	[M-H]-	171.9	32859911
AllCCS	[M+Na-2H]-	170.3	32859911
AllCCS	[M+HCOO]-	168.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	7.59 minutes	32390414
Predicted by Siyang on May 30, 2022	21.4399 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2810.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	781.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	313.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	474.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	499.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	936.4 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	1020.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	68.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1677.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	830.3 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	2177.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	660.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	611.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	698.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	547.0 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	11.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzo[a]pyrene-7,8-oxide	O1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C12	4274.1	Standard polar	33892256
Benzo[a]pyrene-7,8-oxide	O1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C12	2605.0	Standard non polar	33892256
Benzo[a]pyrene-7,8-oxide	O1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C12	3026.1	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[a]pyrene-7,8-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-1090000000-4b9ffcf6ba52ad9a6772	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene-7,8-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-oxide 10V, Positive-QTOF	splash10-014i-0090000000-6dd249213c7d7f2ce33b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 20V, Positive-QTOF	splash10-014i-0090000000-201806979a0265392991	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 40V, Positive-QTOF	splash10-0fb9-0090000000-b00168fdb22eae96a135	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 10V, Negative-QTOF	splash10-014i-0090000000-1ed0e0bd5b5d9a23a8a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 20V, Negative-QTOF	splash10-014i-0090000000-2306ec9feeafd317f3ab	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 40V, Negative-QTOF	splash10-00mo-0090000000-18478cdd5aa3249d8f5b	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

C14850

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

37455

PDB ID

Not Available

ChEBI ID

34563

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Epoxide hydrolase 1

General function:: Involved in catalytic activity
Specific function:: Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:: EPHX1
Uniprot ID:: P07099
Molecular weight:: 52948.48

Reactions

Benzo[a]pyrene-7,8-oxide + Water → Benzo[a]pyrene-7,8-diol	details

Showing metabocard for Benzo[a]pyrene-7,8-oxide (HMDB0060439)

MOL for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

3D MOL for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

3D SDF for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

3D-SDF for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

PDB for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

3D PDB for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

SMILES for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

INCHI for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

Structure for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

3D Structure for HMDB0060439 (Benzo[a]pyrene-7,8-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions