MiMeDB: Showing metabocard for Benzo[a]pyrene-4,5-oxide (MMDBc0030039)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:51:38 UTC

Update Date

2024-04-30 19:44:09 UTC

Metabolite ID

MMDBc0030039

Metabolite Identification

Common Name

Benzo[a]pyrene-4,5-oxide

Description

Benzo[a]pyrene-4,5-oxide is a member of the chemical class known as Chrysenes. These are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene. In the absence of the ycbX- and yiiM-dependent pathways, biotin sulfoxide reductase plays also a role in the detoxification pathway. (PMID 18312271 )

Structure

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

HMDB0060091
     RDKit          3D
Benzo[a]pyrene-4,5-oxide
 33 38  0  0  0  0  0  0  0  0999 V2000
    4.6190    0.8366   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.4998   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230   -1.0553   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312   -0.2277   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    1.1431   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5340    1.6583    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1796    1.9770    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    1.4969    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3412    0.1463   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495   -0.7231   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.0714   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -2.5642   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -1.6990   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655   -2.1326   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -1.2571   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0217    0.0783   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108    0.5575    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389   -0.3239   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    1.9414   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802    3.0782    0.3239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.2583    0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6398    1.2456   -0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2416   -1.1367   -0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -2.1129   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100    2.7084    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    3.0429    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -2.7524   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449   -3.6187   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3343   -3.2070   -0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2303   -1.6343   -0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    0.8373    0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    2.0399   -1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743    1.9702    1.7791 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
  6  1  1  0
 21  8  1  0
 10  4  1  0
 18 13  1  0
 21 19  1  0
 18  9  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
M  END

Structure #1
  Mrv0541 02241207002D          

 21 26  0  0  0  0            999 V2000
    4.5908   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8903   -1.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -2.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -3.1637    0.0000 O   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  6  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4 12  2  0  0  0  0
  5 11  1  0  0  0  0
  6 13  2  0  0  0  0
  7 15  2  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 18  2  0  0  0  0
 15 17  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030039

> <DATABASE_NAME>
MIME

> <SMILES>
O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3

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

> <INCHI_KEY>
XGZQLNASOQVQTD-UHFFFAOYSA-N

> <FORMULA>
C20H12O

> <MOLECULAR_WEIGHT>
268.3087

> <EXACT_MASS>
268.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
29.84078254063227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
18-oxahexacyclo[10.7.2.0³,⁸.0⁹,²⁰.0¹⁶,²¹.0¹⁷,¹⁹]henicosa-1,3,5,7,9(20),10,12(21),13,15-nonaene

> <ALOGPS_LOGP>
5.24

> <JCHEM_LOGP>
4.516689320333333

> <ALOGPS_LOGS>
-7.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.271506924824319

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
82.9017

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzo(a)pyrene 4,5-oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060091
     RDKit          3D
Benzo[a]pyrene-4,5-oxide
 33 38  0  0  0  0  0  0  0  0999 V2000
    4.6190    0.8366   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.4998   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230   -1.0553   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312   -0.2277   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    1.1431   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5340    1.6583    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1796    1.9770    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    1.4969    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3412    0.1463   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495   -0.7231   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.0714   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -2.5642   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -1.6990   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655   -2.1326   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -1.2571   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0217    0.0783   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108    0.5575    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389   -0.3239   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    1.9414   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802    3.0782    0.3239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.2583    0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6398    1.2456   -0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2416   -1.1367   -0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -2.1129   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100    2.7084    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    3.0429    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -2.7524   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449   -3.6187   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3343   -3.2070   -0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2303   -1.6343   -0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    0.8373    0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    2.0399   -1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743    1.9702    1.7791 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
  6  1  1  0
 21  8  1  0
 10  4  1  0
 18 13  1  0
 21 19  1  0
 18  9  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.569  -1.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.065  -0.376   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.512  -1.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.561  -2.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.504  -0.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.553  -0.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.008  -2.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.016   0.788   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.529   0.497   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.041  -3.868   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.008  -0.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.049  -2.704   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.545  -1.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.033  -0.958   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.504  -2.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.529  -3.577   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.512  -1.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.025  -2.122   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.008  -4.450   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.520  -4.741   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.512  -5.906   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    5    7                                                       
CONECT    4    1   12                                                       
CONECT    5    3   11                                                       
CONECT    6    2   13                                                       
CONECT    7    3   15                                                       
CONECT    8    9   11                                                       
CONECT    9    8   14                                                       
CONECT   10   12   16                                                       
CONECT   11    5    8   17                                                  
CONECT   12    4   10   13                                                  
CONECT   13    6   12   14                                                  
CONECT   14    9   13   18                                                  
CONECT   15    7   17   19                                                  
CONECT   16   10   18   20                                                  
CONECT   17   11   15   18                                                  
CONECT   18   14   16   17                                                  
CONECT   19   15   20   21                                                  
CONECT   20   16   19   21                                                  
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   52    0
END

COMPND    HMDB0060091
HETATM    1  C1  UNL     1       4.619   0.837  -0.149  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.374  -0.500  -0.353  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.123  -1.055  -0.393  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.031  -0.228  -0.219  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.254   1.143  -0.009  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.534   1.658   0.023  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.180   1.977   0.170  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.131   1.497   0.144  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.341   0.146  -0.082  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.750  -0.723  -0.256  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.512  -2.071  -0.375  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.802  -2.564  -0.330  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.860  -1.699  -0.175  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.166  -2.133  -0.196  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.235  -1.257  -0.118  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.022   0.078  -0.021  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.711   0.557   0.004  1.00  0.00           C  
HETATM   18  C18 UNL     1      -1.639  -0.324  -0.056  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.398   1.941  -0.244  1.00  0.00           C  
HETATM   20  O1  UNL     1      -2.180   3.078   0.324  1.00  0.00           O  
HETATM   21  C20 UNL     1      -1.240   2.258   0.655  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.640   1.246  -0.124  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.242  -1.137  -0.488  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.049  -2.113  -0.560  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.710   2.708   0.184  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.275   3.043   0.341  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.302  -2.752  -0.501  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.945  -3.619  -0.419  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.334  -3.207  -0.279  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.230  -1.634  -0.133  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.792   0.837   0.040  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.195   2.040  -1.390  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.374   1.970   1.779  1.00  0.00           H  
CONECT    1    2    2    6   22
CONECT    2    3   23
CONECT    3    4    4   24
CONECT    4    5   10
CONECT    5    6    6    7
CONECT    6   25
CONECT    7    8    8   26
CONECT    8    9   21
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   14   18
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   31
CONECT   17   18   18   19
CONECT   19   20   21   32
CONECT   20   21
CONECT   21   33
END

HMDB0060091
     RDKit          3D
Benzo[a]pyrene-4,5-oxide
 33 38  0  0  0  0  0  0  0  0999 V2000
    4.6190    0.8366   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740   -0.4998   -0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230   -1.0553   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312   -0.2277   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    1.1431   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5340    1.6583    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1796    1.9770    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    1.4969    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3412    0.1463   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495   -0.7231   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.0714   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -2.5642   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -1.6990   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655   -2.1326   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -1.2571   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0217    0.0783   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108    0.5575    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389   -0.3239   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    1.9414   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1802    3.0782    0.3239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.2583    0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6398    1.2456   -0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2416   -1.1367   -0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -2.1129   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100    2.7084    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    3.0429    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -2.7524   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449   -3.6187   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3343   -3.2070   -0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2303   -1.6343   -0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    0.8373    0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    2.0399   -1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3743    1.9702    1.7791 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
  6  1  1  0
 21  8  1  0
 10  4  1  0
 18 13  1  0
 21 19  1  0
 18  9  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 21 33  1  0
M  END

Synonyms

Value	Source
Benzo[a]pyrene-4,5-epoxide	Kegg
3b,4a-Dihydrobenzo(1,2)pyreno(4,5-b)oxirene	HMDB
4,5-Dihydro-4,5-epoxybenzo(a)pyrene	HMDB
Benzo(a)pyrene 4,5-epoxide, (+-)-isomer	HMDB
Benzo(a)pyrene 4,5-oxide	HMDB
Benzo(a)pyrene 4,5-epoxide	MeSH

Molecular Formula

C₂₀H₁₂O

Average Mass

268.3087

Monoisotopic Mass

268.088815006

IUPAC Name

18-oxahexacyclo[10.7.2.0³,⁸.0⁹,²⁰.0¹⁶,²¹.0¹⁷,¹⁹]henicosa-1,3,5,7,9(20),10,12(21),13,15-nonaene

Traditional Name

benzo(a)pyrene 4,5-oxide

CAS Registry Number

37574-47-3

SMILES

O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3

InChI Identifier

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

InChI Key

XGZQLNASOQVQTD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Chrysenes

Direct Parent

Chrysenes

Alternative Parents

Substituents

Chrysene
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

carbopolycyclic compound (CHEBI:34560 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.6e-05 g/L	ALOGPS
logP	5.24	ALOGPS
logP	4.52	ChemAxon
logS	-7.2	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	82.9 m³·mol⁻¹	ChemAxon
Polarizability	29.84 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-0090000000-a0acee16644b56de8a87	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-a5fc140110d675a8f67f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0090000000-265bb670b8409fa79f1a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufu-1090000000-8be0bcddc8e600a81d8f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-a54043fd1ab8580b6ed2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-9869044ce7dbcc294175	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ou-0090000000-ebe5c29fe92744c28350	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192428	Glutathione S-transferase Mu 2	Enzyme	P28161	Homo sapiens
MMDBp0192431	Glutathione S-transferase Mu 1	Enzyme	P09488	Homo sapiens
MMDBp0192433	Glutathione S-transferase kappa 1	Enzyme	Q9Y2Q3	Homo sapiens
MMDBp0192434	Microsomal glutathione S-transferase 3	Enzyme	O14880	Homo sapiens
MMDBp0192435	Glutathione S-transferase Mu 3	Enzyme	P21266	Homo sapiens
MMDBp0192436	Glutathione S-transferase A1	Enzyme	P08263	Homo sapiens
MMDBp0192438	Microsomal glutathione S-transferase 1	Enzyme	P10620	Homo sapiens
MMDBp0192439	Glutathione S-transferase Mu 4	Enzyme	Q03013	Homo sapiens
MMDBp0192440	Glutathione S-transferase Mu 5	Enzyme	P46439	Homo sapiens
MMDBp0192441	Microsomal glutathione S-transferase 2	Enzyme	Q99735	Homo sapiens
MMDBp0192442	Glutathione S-transferase omega-1	Enzyme	P78417	Homo sapiens
MMDBp0192443	Glutathione S-transferase A5	Enzyme	Q7RTV2	Homo sapiens
MMDBp0192444	Glutathione S-transferase A2	Enzyme	P09210	Homo sapiens
MMDBp0192446	Glutathione S-transferase A3	Enzyme	Q16772	Homo sapiens
MMDBp0192447	Glutathione S-transferase A4	Enzyme	O15217	Homo sapiens
MMDBp0192451	Glutathione S-transferase omega-2	Enzyme	Q9H4Y5	Homo sapiens
MMDBp0192452	Glutathione S-transferase theta-1	Unknown	P30711	Homo sapiens
MMDBp0192454	Glutathione S-transferase P	Enzyme	P09211	Homo sapiens
MMDBp0196825	Glutathione S-transferase theta-2B	Unknown	P0CG30

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0004982	Benzo[a]pyrene-4,5-oxide	Benzo[A]Pyrene-4,5-Diol	Epoxide hydrolase 2, cytoplasmic	Microsomal Epoxide Hydrolase	VMH	30371894
MMDBr0004983	Benzo[a]pyrene-4,5-oxide	Benzo[A]Pyrene-4,5-Diol	Epoxide hydrolase 1, microsomal (xenobiotic)	Microsomal Epoxide Hydrolase	VMH	30371894
MMDBr0004984	Benzo[a]pyrene-4,5-oxide	Benzo[A]Pyrene-4,5-Diol	Epoxide hydrolase 2, cytoplasmic	Microsomal Epoxide Hydrolase	VMH	30371894
MMDBr0010455	Benzpyrene	Benzo[a]pyrene-4,5-oxide	Cytochrome p450, family 1, subfamily a, polypeptide 1	Benzpyrene, NADPH:Oxygen Oxidoreductase (Rh-Hydroxylating Or -Epoxidizing)	VMH; KEGG	30371894
MMDBr0010456	4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	Benzo[a]pyrene-4,5-oxide	Glutathione s-transferase alpha 1	4, 5-Dihydro-4-Hydroxy-5-S-Glutathionyl-Benzo[A]Pyrene Glutathione-Lyase (Epoxide-Forming)	VMH; KEGG	30371894
MMDBr0019196	Glutathione	1-Amino-2-propanol	Glutathione S-transferase GstA	Conjugation of reduced glutathione	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0060091

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

C14851

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

37786

PDB ID

Not Available

ChEBI ID

34560

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for Benzo[a]pyrene-4,5-oxide (MMDBc0030039)

MOL for #<Metabolite:0x00007fa49c052bf0>

3D MOL for #<Metabolite:0x00007fa49c052bf0>

3D SDF for #<Metabolite:0x00007fa49c052bf0>

3D-SDF for #<Metabolite:0x00007fa49c052bf0>

PDB for #<Metabolite:0x00007fa49c052bf0>

3D PDB for #<Metabolite:0x00007fa49c052bf0>

SMILES for #<Metabolite:0x00007fa49c052bf0>

INCHI for #<Metabolite:0x00007fa49c052bf0>

Structure for #<Metabolite:0x00007fa49c052bf0>

3D Structure for #<Metabolite:0x00007fa49c052bf0>