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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:28:32 UTC

Update Date

2021-09-26 22:59:36 UTC

HMDB ID

HMDB0249009

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dibenz[a,c]anthracene

Description

benzo[f]tetraphene, also known as benzotriphenylene or dibenz(a,c)anthracene, belongs to the class of organic compounds known as triphenylenes. Triphenylenes are compounds containing a triphenylene moiety, which consists of four fused benzene rings forming a 9,10-benzo[l]phenanthrene. Based on a literature review very few articles have been published on benzo[f]tetraphene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dibenz[a,c]anthracene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dibenz[a,c]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

HMDB0249009
     RDKit          3D
Dibenz[a,c]anthracene
 36 40  0  0  0  0  0  0  0  0999 V2000
    4.9894    0.2811    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9202   -1.0916    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -1.6866    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -0.9095    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -1.4969   -0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -0.7488   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -1.3214   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063   -2.6957   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719   -3.2560   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003   -2.4772   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4785   -1.0884   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2408   -0.5027   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1304    0.8744   -0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    1.6579   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1433    3.0497   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    3.6097    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432    2.8405    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662    1.4752    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    0.6445    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847    1.2308    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    0.4544    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    1.0927    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9530    0.7553    0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -1.7172    0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6258   -2.7707    0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -2.5633   -0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -3.3845   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5410   -4.3542   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5771   -2.9506   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3666   -0.4890   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703    1.3102   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0158    3.6946   -0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355    4.7070    0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1752    3.3765    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5823    2.2933    0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    2.1566    0.1703 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
  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
 20 21  1  0
 21 22  2  0
 22  1  1  0
 21  4  1  0
 19  6  1  0
 12  7  1  0
 18 13  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 22 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
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    3.5724    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    3.5724    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
    0.4125    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
   -3.3000    2.8579    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    2.8579    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
   -0.8250    1.4290    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
   -0.4125    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
   -2.8875    2.1434    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    2.1434    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
   -1.6500    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
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 15  2  0  0  0  0
  8 16  2  0  0  0  0
  9 17  2  0  0  0  0
 10 18  2  0  0  0  0
 11 19  2  0  0  0  0
 12 20  2  0  0  0  0
 13 15  1  0  0  0  0
 13 21  2  0  0  0  0
 14 16  1  0  0  0  0
 14 22  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249009

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=C2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC2=C1

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

> <INCHI_KEY>
RAASUWZPTOJQAY-UHFFFAOYSA-N

> <FORMULA>
C22H14

> <MOLECULAR_WEIGHT>
278.354

> <EXACT_MASS>
278.109550451

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.69848872846849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(22),2,4,6,8,10,12,14,16,18,20-undecaene

> <ALOGPS_LOGP>
6.93

> <JCHEM_LOGP>
5.931152842666667

> <ALOGPS_LOGS>
-8.68

> <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>
5.87e-07 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(22),2,4,6,8,10,12,14,16,18,20-undecaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249009
     RDKit          3D
Dibenz[a,c]anthracene
 36 40  0  0  0  0  0  0  0  0999 V2000
    4.9894    0.2811    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9202   -1.0916    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -1.6866    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -0.9095    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -1.4969   -0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -0.7488   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -1.3214   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063   -2.6957   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719   -3.2560   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003   -2.4772   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4785   -1.0884   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2408   -0.5027   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1304    0.8744   -0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    1.6579   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1433    3.0497   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    3.6097    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432    2.8405    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662    1.4752    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    0.6445    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847    1.2308    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    0.4544    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    1.0927    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9530    0.7553    0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -1.7172    0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6258   -2.7707    0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -2.5633   -0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -3.3845   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5410   -4.3542   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5771   -2.9506   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3666   -0.4890   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703    1.3102   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0158    3.6946   -0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355    4.7070    0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1752    3.3765    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5823    2.2933    0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    2.1566    0.1703 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
  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
 20 21  1  0
 21 22  2  0
 22  1  1  0
 21  4  1  0
 19  6  1  0
 12  7  1  0
 18 13  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 22 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       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.390   6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.470   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.850   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.700   0.000   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      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.160   5.335   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   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.160   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.080   0.000   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      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.160   2.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.850   4.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    5    9                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   12                                                       
CONECT    7    1   15                                                       
CONECT    8    2   16                                                       
CONECT    9    3   17                                                       
CONECT   10    4   18                                                       
CONECT   11    5   19                                                       
CONECT   12    6   20                                                       
CONECT   13   15   21                                                       
CONECT   14   16   22                                                       
CONECT   15    7   13   16                                                  
CONECT   16    8   14   15                                                  
CONECT   17    9   18   19                                                  
CONECT   18   10   17   20                                                  
CONECT   19   11   17   21                                                  
CONECT   20   12   18   22                                                  
CONECT   21   13   19   22                                                  
CONECT   22   14   20   21                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0249009
HETATM    1  C1  UNL     1       4.989   0.281   0.153  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.920  -1.092   0.115  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.681  -1.687   0.063  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.544  -0.910   0.050  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.284  -1.497  -0.002  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.131  -0.749  -0.016  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.119  -1.321  -0.067  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.206  -2.696  -0.106  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.472  -3.256  -0.157  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.600  -2.477  -0.170  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.479  -1.088  -0.130  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.241  -0.503  -0.079  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.130   0.874  -0.039  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.259   1.658  -0.052  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.143   3.050  -0.012  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.885   3.610   0.040  1.00  0.00           C  
HETATM   17  C17 UNL     1      -0.743   2.840   0.053  1.00  0.00           C  
HETATM   18  C18 UNL     1      -0.866   1.475   0.013  1.00  0.00           C  
HETATM   19  C19 UNL     1       0.255   0.644   0.024  1.00  0.00           C  
HETATM   20  C20 UNL     1       1.485   1.231   0.076  1.00  0.00           C  
HETATM   21  C21 UNL     1       2.655   0.454   0.089  1.00  0.00           C  
HETATM   22  C22 UNL     1       3.874   1.093   0.142  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.953   0.755   0.193  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.812  -1.717   0.125  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.626  -2.771   0.033  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.261  -2.563  -0.030  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.382  -3.385  -0.100  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.541  -4.354  -0.188  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.577  -2.951  -0.211  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.367  -0.489  -0.140  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.270   1.310  -0.090  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.016   3.695  -0.020  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.836   4.707   0.070  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.175   3.377   0.094  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.582   2.293   0.106  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.904   2.157   0.170  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   24
CONECT    3    4    4   25
CONECT    4    5   21
CONECT    5    6    6   26
CONECT    6    7   19
CONECT    7    8    8   12
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13
CONECT   13   14   14   18
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19
CONECT   19   20   20
CONECT   20   21   35
CONECT   21   22   22
CONECT   22   36
END

HMDB0249009
     RDKit          3D
Dibenz[a,c]anthracene
 36 40  0  0  0  0  0  0  0  0999 V2000
    4.9894    0.2811    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9202   -1.0916    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -1.6866    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -0.9095    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -1.4969   -0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -0.7488   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -1.3214   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063   -2.6957   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4719   -3.2560   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003   -2.4772   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4785   -1.0884   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2408   -0.5027   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1304    0.8744   -0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    1.6579   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1433    3.0497   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    3.6097    0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432    2.8405    0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662    1.4752    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    0.6445    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847    1.2308    0.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    0.4544    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    1.0927    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9530    0.7553    0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -1.7172    0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6258   -2.7707    0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -2.5633   -0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -3.3845   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5410   -4.3542   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5771   -2.9506   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3666   -0.4890   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2703    1.3102   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0158    3.6946   -0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8355    4.7070    0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1752    3.3765    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5823    2.2933    0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    2.1566    0.1703 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
  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
 20 21  1  0
 21 22  2  0
 22  1  1  0
 21  4  1  0
 19  6  1  0
 12  7  1  0
 18 13  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzo[b]triphenylene	Kegg
Benzotriphenylene	Kegg
1,2,3,4-Dibenzanthracene	MeSH
Benzo(b)triphenylene	MeSH
Dibenz(a,c)anthracene	MeSH
Dibenzo(a,c)anthracene	MeSH

Chemical Formula

C₂₂H₁₄

Average Molecular Weight

278.354

Monoisotopic Molecular Weight

278.109550451

IUPAC Name

pentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(22),2,4,6,8,10,12,14,16,18,20-undecaene

Traditional Name

pentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(22),2,4,6,8,10,12,14,16,18,20-undecaene

CAS Registry Number

Not Available

SMILES

C1=CC=C2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC2=C1

InChI Identifier

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

InChI Key

RAASUWZPTOJQAY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triphenylenes. Triphenylenes are compounds containing a triphenylene moiety, which consists of four fused benzene rings forming a 9,10-benzo[l]phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Triphenylenes

Direct Parent

Triphenylenes

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

carbopolycyclic compound (CHEBI:82437 )

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	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	32.7 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+H]+	173.844	30932474
DeepCCS	[M-H]-	171.486	30932474
DeepCCS	[M-2H]-	204.806	30932474
DeepCCS	[M+Na]+	180.033	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.2	32859911
AllCCS	[M-H]-	170.0	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	166.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	25.1711 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.83 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3755.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	953.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	365.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	611.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	736.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1171.3 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	1323.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1986.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	932.2 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	2614.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	714.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	729.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	987.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	558.5 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	84.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dibenz[a,c]anthracene	C1=CC=C2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC2=C1	4310.3	Standard polar	33892256
Dibenz[a,c]anthracene	C1=CC=C2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC2=C1	3136.4	Standard non polar	33892256
Dibenz[a,c]anthracene	C1=CC=C2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC2=C1	3168.7	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,c]anthracene GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0090000000-e1ce3386049e9597145f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dibenz[a,c]anthracene 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 - Dibenz[a,c]anthracene 10V, Positive-QTOF	splash10-004i-0090000000-a1fad70bc82276bcac28	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,c]anthracene 20V, Positive-QTOF	splash10-004i-0090000000-a5edc66a6ad5477b71b1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,c]anthracene 40V, Positive-QTOF	splash10-0fb9-0090000000-5b78c4ace1ea24809066	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,c]anthracene 10V, Negative-QTOF	splash10-004i-0090000000-b378317029404ab7883e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,c]anthracene 20V, Negative-QTOF	splash10-004i-0090000000-b378317029404ab7883e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,c]anthracene 40V, Negative-QTOF	splash10-004i-0090000000-3acb0c13ce12682559d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,c]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,c]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,c]anthracene 40V, Positive-QTOF	splash10-004i-0090000000-90f642c5a50b3a056759	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dibenz[a,c]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,c]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,c]anthracene 40V, Negative-QTOF	splash10-004i-0090000000-f1f000ca3cb2151d263d	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

8810

KEGG Compound ID

C19388

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9164

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 Dibenz[a,c]anthracene (HMDB0249009)

MOL for HMDB0249009 (Dibenz[a,c]anthracene)

3D MOL for HMDB0249009 (Dibenz[a,c]anthracene)

3D SDF for HMDB0249009 (Dibenz[a,c]anthracene)

3D-SDF for HMDB0249009 (Dibenz[a,c]anthracene)

PDB for HMDB0249009 (Dibenz[a,c]anthracene)

3D PDB for HMDB0249009 (Dibenz[a,c]anthracene)

SMILES for HMDB0249009 (Dibenz[a,c]anthracene)

INCHI for HMDB0249009 (Dibenz[a,c]anthracene)

Structure for HMDB0249009 (Dibenz[a,c]anthracene)

3D Structure for HMDB0249009 (Dibenz[a,c]anthracene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra