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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:27:49 UTC

Update Date

2021-09-26 22:59:35 UTC

HMDB ID

HMDB0249000

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzo(a)pyrene-3,6-quinone

Description

Benzo(a)pyrene-3,6-quinone belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Based on a literature review a small amount of articles have been published on Benzo(a)pyrene-3,6-quinone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzo(a)pyrene-3,6-quinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzo(a)pyrene-3,6-quinone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249000
     RDKit          3D
Benzo(a)pyrene-3,6-quinone
 32 36  0  0  0  0  0  0  0  0999 V2000
   -4.8947    1.6639    0.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0587    0.7411    0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588   -0.6308    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355   -1.5648    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201   -1.2604    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165   -2.3001    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1418   -2.0452    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567   -0.7774    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3460    0.2856   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631    1.5741   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890    2.5620   -0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    2.3371   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6414    1.0404    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131    0.0318    0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    1.8798   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    3.0457   -0.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325    0.8120   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7991    1.0692   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913    0.0378   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -1.2355   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9027   -1.5157    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976   -0.4833   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5097   -0.9131    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189   -2.6125    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501   -3.3206    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8156   -2.8741    0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5565    3.5913   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822    3.0960   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0945    2.1011   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7670    0.2332   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990   -2.0358   -0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6345   -2.5328    0.2319 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13  2  1  0
 22 17  1  0
 14  5  2  0
 22  8  1  0
 14  9  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END


  Mrv1652309112105282D          

 22 26  0  0  0  0            999 V2000
    6.4641    1.0361    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
    6.1941   -0.3671    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
    5.1139    0.5684    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
    4.3038    0.7243    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
    4.0337   -0.6789    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
    2.6835   -1.1466    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
    2.9535    0.2566    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
    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
    1.8734    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.0632   -0.8348    0.0000 O   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
    5.1139   -1.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  7 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249000

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C=CC2=C3C1=CC=C1C(=O)C4=CC=CC=C4C(C=C2)=C31

> <INCHI_IDENTIFIER>
InChI=1S/C20H10O2/c21-17-10-6-11-5-7-13-12-3-1-2-4-14(12)20(22)16-9-8-15(17)18(11)19(13)16/h1-10H

> <INCHI_KEY>
MYRYNZSMCVOJHZ-UHFFFAOYSA-N

> <FORMULA>
C20H10O2

> <MOLECULAR_WEIGHT>
282.298

> <EXACT_MASS>
282.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
30.05204110460443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(19),2,4,6,9,11,14,16(20),17-nonaene-8,13-dione

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
4.039888833

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.969203779017363

> <JCHEM_PKA_STRONGEST_BASIC>
-7.155785306924841

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
86.92289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(19),2,4,6,9,11,14,16(20),17-nonaene-8,13-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249000
     RDKit          3D
Benzo(a)pyrene-3,6-quinone
 32 36  0  0  0  0  0  0  0  0999 V2000
   -4.8947    1.6639    0.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0587    0.7411    0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588   -0.6308    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355   -1.5648    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201   -1.2604    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165   -2.3001    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1418   -2.0452    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567   -0.7774    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3460    0.2856   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631    1.5741   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890    2.5620   -0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    2.3371   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6414    1.0404    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131    0.0318    0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    1.8798   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    3.0457   -0.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325    0.8120   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7991    1.0692   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913    0.0378   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -1.2355   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9027   -1.5157    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976   -0.4833   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5097   -0.9131    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189   -2.6125    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501   -3.3206    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8156   -2.8741    0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5565    3.5913   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822    3.0960   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0945    2.1011   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7670    0.2332   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990   -2.0358   -0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6345   -2.5328    0.2319 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13  2  1  0
 22 17  1  0
 14  5  2  0
 22  8  1  0
 14  9  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      12.066   1.934   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.570   0.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.562  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.050  -0.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.546   1.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.554   2.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.034   1.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.026   0.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.530  -1.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.521  -2.431   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.009  -2.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.505  -0.685   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.513   0.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.009   1.934   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.017   3.098   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.530   2.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.497   2.225   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.489   1.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.993  -0.394   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.985  -1.558   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.042  -1.558   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.546  -3.013   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   16                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    7                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19                                                            
CONECT   21    9    4   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0249000
HETATM    1  O1  UNL     1      -4.895   1.664   0.078  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.059   0.741   0.172  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.459  -0.631   0.430  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.535  -1.565   0.519  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.120  -1.260   0.365  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.216  -2.300   0.473  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.142  -2.045   0.332  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.557  -0.777   0.090  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.346   0.286  -0.023  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.063   1.574  -0.268  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.889   2.562  -0.364  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.222   2.337  -0.229  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.641   1.040   0.018  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.713   0.032   0.119  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.469   1.880  -0.421  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.899   3.046  -0.648  1.00  0.00           O  
HETATM   17  C15 UNL     1       2.432   0.812  -0.313  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.799   1.069  -0.456  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.691   0.038  -0.348  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.249  -1.235  -0.103  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.903  -1.516   0.042  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.998  -0.483  -0.065  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.510  -0.913   0.554  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.819  -2.613   0.715  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.550  -3.321   0.668  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.816  -2.874   0.421  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.557   3.591  -0.560  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.982   3.096  -0.301  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.094   2.101  -0.650  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.767   0.233  -0.459  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.999  -2.036  -0.024  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.635  -2.533   0.232  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6   14   14
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   22
CONECT    9   10   14
CONECT   10   11   11   15
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14
CONECT   15   16   16   17
CONECT   17   18   18   22
CONECT   18   19   29
CONECT   19   20   20   30
CONECT   20   21   31
CONECT   21   22   22   32
END

HMDB0249000
     RDKit          3D
Benzo(a)pyrene-3,6-quinone
 32 36  0  0  0  0  0  0  0  0999 V2000
   -4.8947    1.6639    0.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0587    0.7411    0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588   -0.6308    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355   -1.5648    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1201   -1.2604    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165   -2.3001    0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1418   -2.0452    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567   -0.7774    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3460    0.2856   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631    1.5741   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8890    2.5620   -0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    2.3371   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6414    1.0404    0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131    0.0318    0.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    1.8798   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    3.0457   -0.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325    0.8120   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7991    1.0692   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913    0.0378   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -1.2355   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9027   -1.5157    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976   -0.4833   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5097   -0.9131    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8189   -2.6125    0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5501   -3.3206    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8156   -2.8741    0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5565    3.5913   -0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822    3.0960   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0945    2.1011   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7670    0.2332   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990   -2.0358   -0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6345   -2.5328    0.2319 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 10 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13  2  1  0
 22 17  1  0
 14  5  2  0
 22  8  1  0
 14  9  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
 21 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,6-Benzo(a)pyrenequinone	HMDB
Benzo(a)pyrene-3,6-dione	HMDB
Benzo(a)pyrene-3,6-quinone	MeSH

Chemical Formula

C₂₀H₁₀O₂

Average Molecular Weight

282.298

Monoisotopic Molecular Weight

282.068079562

IUPAC Name

pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(19),2,4,6,9,11,14,16(20),17-nonaene-8,13-dione

Traditional Name

pentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(19),2,4,6,9,11,14,16(20),17-nonaene-8,13-dione

CAS Registry Number

Not Available

SMILES

O=C1C=CC2=C3C1=CC=C1C(=O)C4=CC=CC=C4C(C=C2)=C31

InChI Identifier

InChI=1S/C20H10O2/c21-17-10-6-11-5-7-13-12-3-1-2-4-14(12)20(22)16-9-8-15(17)18(11)19(13)16/h1-10H

InChI Key

MYRYNZSMCVOJHZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzo-a-pyrene
Chrysene
Phenanthrene
Anthracene
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.13	ALOGPS
logP	4.04	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	15.97	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.92 m³·mol⁻¹	ChemAxon
Polarizability	30.05 Å³	ChemAxon
Number of Rings	5	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
DeepCCS	[M-2H]-	210.331	30932474
DeepCCS	[M+Na]+	185.559	30932474
AllCCS	[M+H]+	165.9	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	169.3	32859911
AllCCS	[M+Na]+	170.3	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	169.4	32859911
AllCCS	[M+HCOO]-	167.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	16.096 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2749.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	511.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	204.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	280.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	627.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	654.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1515.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	536.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1493.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	500.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	456.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	436.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	473.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	64.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzo(a)pyrene-3,6-quinone	O=C1C=CC2=C3C1=CC=C1C(=O)C4=CC=CC=C4C(C=C2)=C31	4402.9	Standard polar	33892256
Benzo(a)pyrene-3,6-quinone	O=C1C=CC2=C3C1=CC=C1C(=O)C4=CC=CC=C4C(C=C2)=C31	3095.3	Standard non polar	33892256
Benzo(a)pyrene-3,6-quinone	O=C1C=CC2=C3C1=CC=C1C(=O)C4=CC=CC=C4C(C=C2)=C31	3065.2	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-3,6-quinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0090000000-9d8b54b728eee1001019	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzo(a)pyrene-3,6-quinone 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-3,6-quinone 10V, Positive-QTOF	splash10-001i-0090000000-dad6fc977489850fa3a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo(a)pyrene-3,6-quinone 20V, Positive-QTOF	splash10-001i-0090000000-dad6fc977489850fa3a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo(a)pyrene-3,6-quinone 40V, Positive-QTOF	splash10-0a59-0090000000-96fd6549c5c2e94383f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo(a)pyrene-3,6-quinone 10V, Negative-QTOF	splash10-001i-0090000000-8c66bc3caa5b95965133	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo(a)pyrene-3,6-quinone 20V, Negative-QTOF	splash10-001i-0090000000-8c66bc3caa5b95965133	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzo(a)pyrene-3,6-quinone 40V, Negative-QTOF	splash10-0f89-0090000000-7e13cbe62db414bc802a	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

17286

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18301

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Benzo(a)pyrene-3,6-quinone (HMDB0249000)

MOL for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

3D MOL for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

3D SDF for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

3D-SDF for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

PDB for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

3D PDB for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

SMILES for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

INCHI for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

Structure for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

3D Structure for HMDB0249000 (Benzo(a)pyrene-3,6-quinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra