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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-09 20:53:54 UTC

Update Date

2022-03-07 03:17:38 UTC

HMDB ID

HMDB0060091

Secondary Accession Numbers

HMDB60091

Metabolite Identification

Common Name

Benzo[a]pyrene-4,5-oxide

Description

Benzo[a]pyrene-4,5-oxide 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. Benzo[a]pyrene-4,5-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzo[a]pyrene-4,5-oxide exists in all living organisms, ranging from bacteria to humans. These are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzophenanthrene.

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>
HMDB0060091

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₂₀H₁₂O

Average Molecular Weight

268.3087

Monoisotopic Molecular Weight

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

Not Available

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 )

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.212	31661259
DarkChem	[M-H]-	160.098	31661259
DeepCCS	[M-2H]-	202.705	30932474
DeepCCS	[M+Na]+	177.932	30932474
AllCCS	[M+H]+	164.6	32859911
AllCCS	[M+H-H2O]+	160.8	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	169.1	32859911
AllCCS	[M-H]-	171.6	32859911
AllCCS	[M+Na-2H]-	170.0	32859911
AllCCS	[M+HCOO]-	168.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzo[a]pyrene-4,5-oxide	O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3	3916.5	Standard polar	33892256
Benzo[a]pyrene-4,5-oxide	O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3	2596.8	Standard non polar	33892256
Benzo[a]pyrene-4,5-oxide	O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3	2966.9	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-4,5-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-0090000000-a0acee16644b56de8a87	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo[a]pyrene-4,5-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-4,5-oxide 10V, Negative-QTOF	splash10-014i-0090000000-a54043fd1ab8580b6ed2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 20V, Negative-QTOF	splash10-014i-0090000000-9869044ce7dbcc294175	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 40V, Negative-QTOF	splash10-00ou-0090000000-ebe5c29fe92744c28350	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 10V, Positive-QTOF	splash10-014i-0090000000-a5fc140110d675a8f67f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 20V, Positive-QTOF	splash10-014i-0090000000-265bb670b8409fa79f1a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 40V, Positive-QTOF	splash10-0ufu-1090000000-8be0bcddc8e600a81d8f	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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

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

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

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 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Glutathione S-transferase Mu 2

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTM2
Uniprot ID:: P28161
Molecular weight:: 25744.395

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

2. Glutathione S-transferase Mu 1

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTM1
Uniprot ID:: P09488
Molecular weight:: 25711.555

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

3. Glutathione S-transferase kappa 1

General function:: Involved in protein disulfide oxidoreductase activity
Specific function:: Significant glutathione conjugating activity is found only with the model substrate, 1-chloro-2,4-dinitrobenzene (CDNB).
Gene Name:: GSTK1
Uniprot ID:: Q9Y2Q3
Molecular weight:: 31565.605

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

4. Microsomal glutathione S-transferase 3

General function:: Involved in glutathione transferase activity
Specific function:: Also functions as a glutathione peroxidase.
Gene Name:: MGST3
Uniprot ID:: O14880
Molecular weight:: 16516.185

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

5. Glutathione S-transferase Mu 3

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May govern uptake and detoxification of both endogenous compounds and xenobiotics at the testis and brain blood barriers.
Gene Name:: GSTM3
Uniprot ID:: P21266
Molecular weight:: 26559.32

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

6. Glutathione S-transferase A1

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTA1
Uniprot ID:: P08263
Molecular weight:: 25630.785

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

7. Microsomal glutathione S-transferase 1

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a wide substrate specificity.
Gene Name:: MGST1
Uniprot ID:: P10620
Molecular weight:: 17598.45

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

8. Glutathione S-transferase Mu 4

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name:: GSTM4
Uniprot ID:: Q03013
Molecular weight:: 25561.095

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

9. Glutathione S-transferase Mu 5

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTM5
Uniprot ID:: P46439
Molecular weight:: 25674.455

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Enzyme Details

10. Microsomal glutathione S-transferase 2

General function:: Involved in enzyme activator activity
Specific function:: Can catalyze the production of LTC4 from LTA4 and reduced glutathione. Can catalyze the conjugation of 1-chloro-2,4-dinitrobenzene with reduced glutathione.
Gene Name:: MGST2
Uniprot ID:: Q99735
Molecular weight:: 16620.4

Reactions

Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene	details

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Showing metabocard for Benzo[a]pyrene-4,5-oxide (HMDB0060091)

MOL for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

3D MOL for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

3D SDF for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

3D-SDF for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

PDB for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

3D PDB for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

SMILES for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

INCHI for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

Structure for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

3D Structure for HMDB0060091 (Benzo[a]pyrene-4,5-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions