MiMeDB: Showing metabocard for Benzo[a]pyrene-7,8-diol (MMDBc0030040)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:51:40 UTC

Update Date

2024-04-30 19:44:11 UTC

Metabolite ID

MMDBc0030040

Metabolite Identification

Common Name

Benzo[a]pyrene-7,8-diol

Description

Benzo[a]pyrene-7,8-diol is a member of the chemical class known as Pyrenes. These are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system. Benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide (BPDE), a metabolite of the widespread environmental pollutant benzo[a]pyrene, is a mutagenic in both bacterial and mammalian systems. (PMID 7890605 )

Structure

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

HMDB0249735
     RDKit          3D
(E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol
 36 40  0  0  0  0  0  0  0  0999 V2000
    5.0685    0.5866   -1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1347    0.4516   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484    1.7306    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1398    1.8617    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    0.7117   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -0.5233   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -1.6522   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3495   -1.4832   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1623   -2.5745   -0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -2.4863   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0627   -1.2306   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513   -1.0972   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0170    0.1385   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1867    1.2325    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167    1.1103    0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    2.2171    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6258    2.1149    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.8713    0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949   -0.2425   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650   -0.1344   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819   -0.7218   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6860   -1.7510    0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7757    1.2182   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111    0.2541    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552    2.6039    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    2.8232    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935   -2.6025   -0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7397   -3.5486   -0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2068   -3.3159   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0705   -1.9799   -0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0930    0.2271   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.1923    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205    3.1620    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    3.0225    0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -1.1536   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5797   -2.0326    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  1  0
 21  2  1  0
 18  5  1  0
 19  8  1  0
 20 11  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 21 35  1  0
 22 36  1  0
M  END

Structure #1
  Mrv0541 02241207002D          

 22 26  0  0  0  0            999 V2000
    1.3333    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6540    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7342    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9535    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  2  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  7 15  1  0  0  0  0
  8  9  2  0  0  0  0
  8 14  1  0  0  0  0
  9 17  1  0  0  0  0
 10 13  1  0  0  0  0
 10 16  2  0  0  0  0
 11 18  2  0  0  0  0
 12 18  1  0  0  0  0
 13 19  2  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030040

> <DATABASE_NAME>
MIME

> <SMILES>
OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10,17,20-22H

> <INCHI_KEY>
YDXRLMMGARHIIC-UHFFFAOYSA-N

> <FORMULA>
C20H14O2

> <MOLECULAR_WEIGHT>
286.324

> <EXACT_MASS>
286.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.453707204272707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
3.307152816

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.692725009540293

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.150086073878729

> <JCHEM_PKA_STRONGEST_BASIC>
-3.373702433945751

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
88.04439999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249735
     RDKit          3D
(E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol
 36 40  0  0  0  0  0  0  0  0999 V2000
    5.0685    0.5866   -1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1347    0.4516   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484    1.7306    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1398    1.8617    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    0.7117   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -0.5233   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -1.6522   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3495   -1.4832   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1623   -2.5745   -0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -2.4863   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0627   -1.2306   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513   -1.0972   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0170    0.1385   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1867    1.2325    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167    1.1103    0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    2.2171    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6258    2.1149    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.8713    0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949   -0.2425   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650   -0.1344   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819   -0.7218   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6860   -1.7510    0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7757    1.2182   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111    0.2541    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552    2.6039    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    2.8232    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935   -2.6025   -0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7397   -3.5486   -0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2068   -3.3159   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0705   -1.9799   -0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0930    0.2271   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.1923    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205    3.1620    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    3.0225    0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -1.1536   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5797   -2.0326    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  1  0
 21  2  1  0
 18  5  1  0
 19  8  1  0
 20 11  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 21 35  1  0
 22 36  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       2.489   1.061   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.993  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.497   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.009  -2.140   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.521  -2.431   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.017   3.098   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.530   2.807   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.554   2.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.066   1.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.042  -1.558   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.505  -0.685   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.009   1.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.530  -1.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.546   1.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.034   1.352   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.050  -0.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.571   0.479   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.513   0.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.026   0.188   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.562  -0.685   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.083   0.188   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.066  -2.140   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   22                                                  
CONECT   21   17                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0249735
HETATM    1  O1  UNL     1       5.068   0.587  -1.148  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.135   0.452  -0.079  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.448   1.731   0.150  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.140   1.862   0.177  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.274   0.712  -0.027  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.831  -0.523  -0.250  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.004  -1.652  -0.444  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.350  -1.483  -0.404  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.162  -2.575  -0.592  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.540  -2.486  -0.566  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.063  -1.231  -0.340  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.451  -1.097  -0.306  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.017   0.138  -0.084  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.187   1.233   0.104  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.817   1.110   0.073  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.020   2.217   0.263  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.626   2.115   0.235  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.102   0.871   0.011  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.895  -0.242  -0.181  1.00  0.00           C  
HETATM   20  C19 UNL     1      -2.265  -0.134  -0.152  1.00  0.00           C  
HETATM   21  C20 UNL     1       3.282  -0.722  -0.301  1.00  0.00           C  
HETATM   22  O2  UNL     1       3.686  -1.751   0.573  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.776   1.218  -0.833  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.811   0.254   0.814  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.055   2.604   0.305  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.754   2.823   0.350  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.494  -2.602  -0.616  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.740  -3.549  -0.767  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.207  -3.316  -0.708  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.071  -1.980  -0.458  1.00  0.00           H  
HETATM   31  H9  UNL     1      -6.093   0.227  -0.060  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.646   2.192   0.277  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.520   3.162   0.434  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.092   3.023   0.392  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.524  -1.154  -1.335  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.580  -2.033   0.251  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3   21   24
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   18
CONECT    6    7   21
CONECT    7    8    8   27
CONECT    8    9   19
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   20
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   32
CONECT   15   16   16   20
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19
CONECT   19   20   20
CONECT   21   22   35
CONECT   22   36
END

HMDB0249735
     RDKit          3D
(E)-7,8-Dihydrobenzo(a)pyrene-7,8-diol
 36 40  0  0  0  0  0  0  0  0999 V2000
    5.0685    0.5866   -1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1347    0.4516   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484    1.7306    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1398    1.8617    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    0.7117   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -0.5233   -0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -1.6522   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3495   -1.4832   -0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1623   -2.5745   -0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405   -2.4863   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0627   -1.2306   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513   -1.0972   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0170    0.1385   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1867    1.2325    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167    1.1103    0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    2.2171    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6258    2.1149    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    0.8713    0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949   -0.2425   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650   -0.1344   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819   -0.7218   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6860   -1.7510    0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7757    1.2182   -0.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111    0.2541    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552    2.6039    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544    2.8232    0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935   -2.6025   -0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7397   -3.5486   -0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2068   -3.3159   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0705   -1.9799   -0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0930    0.2271   -0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.1923    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205    3.1620    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    3.0225    0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236   -1.1536   -1.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5797   -2.0326    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  1  0
 21  2  1  0
 18  5  1  0
 19  8  1  0
 20 11  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 21 35  1  0
 22 36  1  0
M  END

Synonyms

Value	Source
Benzo[a]pyrene-7,8-dihydrodiol	Kegg
7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene	HMDB
Benzo(a)pyrene 7,8-dihydrodiol, (7R-trans)-isomer	HMDB
Benzopyrene-7,8-dihydrodiol	HMDB
7,8-Dihydro-7,8-dihydroxybenzopyrene	HMDB
7,8-Dihydrobenzo(a)pyrene-7,8-diol	HMDB
BP-7,8 Diol	HMDB
Benzo(a)pyrene 7,8-dihydrodiol, (cis)-isomer	HMDB
trans-Benzopyrene 7,8-dihydrodiol	HMDB
7,8-Dihydro 7,8-dihydroxybenzo(a)pyrene	HMDB
Benzo(a)pyrene 7,8-dihydrodiol, (trans)-(+-)-isomer	HMDB
Benzo(a)pyrene 7,8-dihydrodiol, (trans)-isomer	HMDB
Benzo(a)pyrene 7,8-dihydrodiol, (7S-trans)-isomer	HMDB
trans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene	HMDB
Benzo(a)pyrene 7,8-dihydrodiol	MeSH

Molecular Formula

C₂₀H₁₄O₂

Average Mass

286.324

Monoisotopic Mass

286.099379692

IUPAC Name

pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol

Traditional Name

benzo(a)pyrene 7,8-diol

CAS Registry Number

13345-25-0

SMILES

OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O

InChI Identifier

InChI=1S/C20H14O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10,17,20-22H

InChI Key

YDXRLMMGARHIIC-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Pyrenes

Sub Class

Not Available

Direct Parent

Pyrenes

Alternative Parents

Substituents

Pyrene
Phenanthrol
Phenanthrene
Naphthalene
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

pyrenes (CHEBI:34562 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	3.61	ALOGPS
logP	3.31	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.15	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.04 m³·mol⁻¹	ChemAxon
Polarizability	31.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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	splash10-056r-0090000000-d0f9942584aaf480d999	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0103-8009100000-fe801e46e710eea32e4f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-e746f506858cf64c915a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9i-1090000000-fcf1f10a896618157892	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-1290000000-d88f3784dd0a513870f4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-7c6172f7110a47ae0a1a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-40d4296cbb4974e7d7c7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a70-1090000000-35194879c01560da4ee1	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	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
MMDBp0193265	Epoxide hydrolase 1	Enzyme	P07099	Homo sapiens
MMDBp0196825	Glutathione S-transferase theta-2B	Unknown	P0CG30

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0010457	Benzo[A]Pyrene-7,8-Oxide	Benzo[a]pyrene-7,8-diol	epoxide hydrolase 1, microsomal (xenobiotic)	VMH; KEGG	30371894
MMDBr0010459	Glutathione	7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene	glutathione S-transferase alpha 1	VMH; KEGG	30371894
MMDBr0010460	Benzo[a]pyrene-7,8-diol	Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide	cytochrome P450, family 1, subfamily A, polypeptide 1	VMH; KEGG	30371894

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

HMDB0060438

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

C14852

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25892

PDB ID

Not Available

ChEBI ID

34562

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 ]

Showing metabocard for Benzo[a]pyrene-7,8-diol (MMDBc0030040)

MOL for #<Metabolite:0x00007fecaba71f80>

3D MOL for #<Metabolite:0x00007fecaba71f80>

3D SDF for #<Metabolite:0x00007fecaba71f80>

3D-SDF for #<Metabolite:0x00007fecaba71f80>

PDB for #<Metabolite:0x00007fecaba71f80>

3D PDB for #<Metabolite:0x00007fecaba71f80>

SMILES for #<Metabolite:0x00007fecaba71f80>

INCHI for #<Metabolite:0x00007fecaba71f80>

Structure for #<Metabolite:0x00007fecaba71f80>

3D Structure for #<Metabolite:0x00007fecaba71f80>