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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:27:54 UTC

Update Date

2021-09-26 23:03:00 UTC

HMDB ID

HMDB0251159

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dibenz[a,h]anthracene

Description

Dibenzo[a,h]anthracene, also known as 1,2:5,6-dibenzanthracene or DBA, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Dibenzo[a,h]anthracene is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Dibenzo[a,h]anthracene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dibenz[a,h]anthracene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dibenz[a,h]anthracene 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

HMDB0251159
     RDKit          3D
Dibenz[a,h]anthracene
 36 40  0  0  0  0  0  0  0  0999 V2000
   -5.4655   -0.6643   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -1.7795   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -1.6217   -0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.3598   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.7530   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9551    0.5996   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439    2.0098   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797    2.1793   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449    1.0898    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379    1.2605    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3883    0.1652    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.1072    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -2.2016    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287   -2.0226    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5656   -0.7594    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9566   -0.6005    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587    0.6774    0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.7753    0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    1.6262    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510    0.3470    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -1.2863    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669   -0.1979    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5534   -0.7623   -0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173   -2.7455   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022   -2.5119   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5435    1.4985   -0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024    2.8880   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    3.1842   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770    2.2835    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585   -3.2054    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -2.8638    0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622   -1.4803    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5382    0.8437    0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1036    2.7749    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    2.5199    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8572   -2.3058    0.1174 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
 18 19  1  0
 19 20  2  0
 12 21  1  0
 21 22  2  0
  6  1  1  0
 22  9  1  0
 22  4  1  0
 20 11  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END


  Mrv1652304272019102D          

 22 26  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5375    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5375   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  5  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5 15  2  0  0  0  0
  6 16  1  0  0  0  0
  7 19  2  0  0  0  0
  8 20  1  0  0  0  0
  9 11  2  0  0  0  0
  9 15  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  2  0  0  0  0
 13 18  1  0  0  0  0
 13 21  2  0  0  0  0
 14 17  2  0  0  0  0
 14 22  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251159

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC2=CC=C3C=C4C(C=CC5=CC=CC=C45)=CC3=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H

> <INCHI_KEY>
LHRCREOYAASXPZ-UHFFFAOYSA-N

> <FORMULA>
C22H14

> <MOLECULAR_WEIGHT>
278.3466

> <EXACT_MASS>
278.109550448

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.86548706449459

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene

> <ALOGPS_LOGP>
6.93

> <JCHEM_LOGP>
5.931152842666667

> <ALOGPS_LOGS>
-8.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
91.85879999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e-07 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0251159
     RDKit          3D
Dibenz[a,h]anthracene
 36 40  0  0  0  0  0  0  0  0999 V2000
   -5.4655   -0.6643   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -1.7795   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -1.6217   -0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.3598   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.7530   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9551    0.5996   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439    2.0098   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797    2.1793   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449    1.0898    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379    1.2605    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3883    0.1652    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.1072    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -2.2016    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287   -2.0226    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5656   -0.7594    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9566   -0.6005    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587    0.6774    0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.7753    0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    1.6262    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510    0.3470    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -1.2863    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669   -0.1979    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5534   -0.7623   -0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173   -2.7455   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022   -2.5119   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5435    1.4985   -0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024    2.8880   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    3.1842   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770    2.2835    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585   -3.2054    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -2.8638    0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622   -1.4803    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5382    0.8437    0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1036    2.7749    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    2.5199    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8572   -2.3058    0.1174 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
 18 19  1  0
 19 20  2  0
 12 21  1  0
 21 22  2  0
  6  1  1  0
 22  9  1  0
 22  4  1  0
 20 11  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.780   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.010   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.010  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.470   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.700  -2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.160  -2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.470  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.700   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.160   0.000   0.000  0.00  0.00           C+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1   15                                                       
CONECT    6    2   16                                                       
CONECT    7    3   19                                                       
CONECT    8    4   20                                                       
CONECT    9   11   15                                                       
CONECT   10   12   16                                                       
CONECT   11    9   17                                                       
CONECT   12   10   18                                                       
CONECT   13   18   21                                                       
CONECT   14   17   22                                                       
CONECT   15    5    9   19                                                  
CONECT   16    6   10   20                                                  
CONECT   17   11   14   21                                                  
CONECT   18   12   13   22                                                  
CONECT   19    7   15   21                                                  
CONECT   20    8   16   22                                                  
CONECT   21   13   17   19                                                  
CONECT   22   14   18   20                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0251159
HETATM    1  C1  UNL     1      -5.465  -0.664  -0.335  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.671  -1.779  -0.229  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.278  -1.622  -0.114  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.747  -0.360  -0.112  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.582   0.753  -0.223  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.955   0.600  -0.335  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.044   2.010  -0.220  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.680   2.179  -0.108  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.845   1.090   0.001  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.538   1.260   0.114  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.388   0.165   0.225  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.853  -1.107   0.223  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.678  -2.202   0.332  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.029  -2.023   0.442  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.566  -0.759   0.444  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.957  -0.600   0.558  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.459   0.677   0.557  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.642   1.775   0.449  1.00  0.00           C  
HETATM   19  C19 UNL     1       3.269   1.626   0.336  1.00  0.00           C  
HETATM   20  C20 UNL     1       2.751   0.347   0.336  1.00  0.00           C  
HETATM   21  C21 UNL     1      -0.536  -1.286   0.110  1.00  0.00           C  
HETATM   22  C22 UNL     1      -1.367  -0.198   0.001  1.00  0.00           C  
HETATM   23  H1  UNL     1      -6.553  -0.762  -0.426  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.117  -2.745  -0.234  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.702  -2.512  -0.034  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.544   1.499  -0.417  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.702   2.888  -0.307  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.240   3.184  -0.105  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.877   2.284   0.108  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.259  -3.205   0.330  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.729  -2.864   0.531  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.562  -1.480   0.640  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.538   0.844   0.644  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.104   2.775   0.454  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.690   2.520   0.255  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.857  -2.306   0.117  1.00  0.00           H  
CONECT    1    2    2    6   23
CONECT    2    3   24
CONECT    3    4    4   25
CONECT    4    5   22
CONECT    5    6    6    7
CONECT    6   26
CONECT    7    8    8   27
CONECT    8    9   28
CONECT    9   10   10   22
CONECT   10   11   29
CONECT   11   12   12   20
CONECT   12   13   21
CONECT   13   14   14   30
CONECT   14   15   31
CONECT   15   16   16   20
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   21   22   22   36
END

HMDB0251159
     RDKit          3D
Dibenz[a,h]anthracene
 36 40  0  0  0  0  0  0  0  0999 V2000
   -5.4655   -0.6643   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -1.7795   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777   -1.6217   -0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.3598   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    0.7530   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9551    0.5996   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439    2.0098   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797    2.1793   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449    1.0898    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379    1.2605    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3883    0.1652    0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8525   -1.1072    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6780   -2.2016    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287   -2.0226    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5656   -0.7594    0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9566   -0.6005    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587    0.6774    0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416    1.7753    0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    1.6262    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510    0.3470    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -1.2863    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669   -0.1979    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5534   -0.7623   -0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1173   -2.7455   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022   -2.5119   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5435    1.4985   -0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024    2.8880   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2397    3.1842   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770    2.2835    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585   -3.2054    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -2.8638    0.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622   -1.4803    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5382    0.8437    0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1036    2.7749    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    2.5199    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8572   -2.3058    0.1174 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
 18 19  1  0
 19 20  2  0
 12 21  1  0
 21 22  2  0
  6  1  1  0
 22  9  1  0
 22  4  1  0
 20 11  1  0
 20 15  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2:5,6-Dibenzanthracene	ChEBI
DBA	ChEBI
1,2,5,6-Dibenzanthracene	MeSH
1,2,5,6-Dibenzanthracene, ion(1+)	MeSH
1,2,5,6-Dibenzanthracene, ion(1-)	MeSH
Dibenz(a,H)anthracene	MeSH
dibenzo(a,H)Anthracene	MeSH

Chemical Formula

C₂₂H₁₄

Average Molecular Weight

278.3466

Monoisotopic Molecular Weight

278.109550448

IUPAC Name

pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene

Traditional Name

pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene

CAS Registry Number

Not Available

SMILES

C1=CC2=CC=C3C=C4C(C=CC5=CC=CC=C45)=CC3=C2C=C1

InChI Identifier

InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H

InChI Key

LHRCREOYAASXPZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Anthracene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

ortho-fused polycyclic arene (CHEBI:35299 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	6.93	ALOGPS
logP	5.93	ChemAxon
logS	-8.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.86 m³·mol⁻¹	ChemAxon
Polarizability	32.87 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]-	215.508	30932474
DeepCCS	[M+Na]+	190.954	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	172.4	32859911
AllCCS	[M+Na]+	173.4	32859911
AllCCS	[M-H]-	170.4	32859911
AllCCS	[M+Na-2H]-	168.7	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dibenz[a,h]anthracene	C1=CC2=CC=C3C=C4C(C=CC5=CC=CC=C45)=CC3=C2C=C1	4418.2	Standard polar	33892256
Dibenz[a,h]anthracene	C1=CC2=CC=C3C=C4C(C=CC5=CC=CC=C45)=CC3=C2C=C1	3162.1	Standard non polar	33892256
Dibenz[a,h]anthracene	C1=CC2=CC=C3C=C4C(C=CC5=CC=CC=C45)=CC3=C2C=C1	3110.3	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 - Dibenz[a,h]anthracene GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0090000000-81693ebd93637cbc7080	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibenz[a,h]anthracene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-0190000000-84d24efcba4eb6b8512e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 10V, Positive-QTOF	splash10-004i-0090000000-3115bf003b9cee611609	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 20V, Positive-QTOF	splash10-004i-0090000000-749c760f7a5a9c1aeeb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 40V, Positive-QTOF	splash10-0fb9-0090000000-e058e0550d22fa7479e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 10V, Negative-QTOF	splash10-004i-0090000000-773f4e4ef9823ddfdea3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 20V, Negative-QTOF	splash10-004i-0090000000-773f4e4ef9823ddfdea3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 40V, Negative-QTOF	splash10-004i-0090000000-910a1e5be083829e5535	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 10V, Positive-QTOF	splash10-004i-0090000000-3ca26a652eff5433f50a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 20V, Positive-QTOF	splash10-004i-0090000000-3ca26a652eff5433f50a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 40V, Positive-QTOF	splash10-004i-0090000000-27ab7759f478445cae3f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 10V, Negative-QTOF	splash10-004i-0090000000-f1f000ca3cb2151d263d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 20V, Negative-QTOF	splash10-004i-0090000000-f1f000ca3cb2151d263d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,h]anthracene 40V, Negative-QTOF	splash10-0fb9-0090000000-46f199df2f90ecf72a7d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

C00017098

Chemspider ID

5678

KEGG Compound ID

C14325

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

35299

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 Dibenz[a,h]anthracene (HMDB0251159)

MOL for HMDB0251159 (Dibenz[a,h]anthracene)

3D MOL for HMDB0251159 (Dibenz[a,h]anthracene)

3D SDF for HMDB0251159 (Dibenz[a,h]anthracene)

3D-SDF for HMDB0251159 (Dibenz[a,h]anthracene)

PDB for HMDB0251159 (Dibenz[a,h]anthracene)

3D PDB for HMDB0251159 (Dibenz[a,h]anthracene)

SMILES for HMDB0251159 (Dibenz[a,h]anthracene)

INCHI for HMDB0251159 (Dibenz[a,h]anthracene)

Structure for HMDB0251159 (Dibenz[a,h]anthracene)

3D Structure for HMDB0251159 (Dibenz[a,h]anthracene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra