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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:26:21 UTC

Update Date

2021-09-26 22:59:33 UTC

HMDB ID

HMDB0248975

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzarone

Description

Benzarone, also known as EHBB, belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. Based on a literature review a significant number of articles have been published on Benzarone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzarone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzarone 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

HMDB0248975
     RDKit          3D
Benzarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.0313   -3.2803    0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997   -2.4323    0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479   -1.0662    0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4913   -0.6286    1.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844    0.6017    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8922    1.3399    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    2.6505    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    3.1174   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8234    2.3429   -0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349    1.0149   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    0.0336   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772    0.0304   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.0210   -2.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    0.0902   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4156    1.1070    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7836    1.0815    0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5826    0.0022    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9402   -0.0088    0.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071   -1.0513   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -1.0057   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469   -2.5587   -0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -4.1513   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6161   -3.3850    1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -2.6790    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -2.5967   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255    0.9960    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8577    3.2573    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408    4.1022   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572    2.6631   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675    1.9615    0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043    1.9001    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5874    0.3524    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203   -1.9510   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -1.8707   -1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  3  2  0
 20 14  1  0
 10  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

  Mrv1652306031606242D          

 20 22  0  0  0  0            999 V2000
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  5  2  0  0  0  0
 14  2  1  0  0  0  0
 15  6  2  0  0  0  0
 15 13  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 11  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19 17  2  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248975

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C(C(=O)C2=CC=C(O)C=C2)C2=CC=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O3/c1-2-14-16(13-5-3-4-6-15(13)20-14)17(19)11-7-9-12(18)10-8-11/h3-10,18H,2H2,1H3

> <INCHI_KEY>
RFRXIWQYSOIBDI-UHFFFAOYSA-N

> <FORMULA>
C17H14O3

> <MOLECULAR_WEIGHT>
266.296

> <EXACT_MASS>
266.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.789500351241575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-ethyl-1-benzofuran-3-carbonyl)phenol

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
4.010240650333333

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.79676701251386

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9827132914624253

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
77.1292

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzarone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248975
     RDKit          3D
Benzarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.0313   -3.2803    0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997   -2.4323    0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479   -1.0662    0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4913   -0.6286    1.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844    0.6017    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8922    1.3399    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    2.6505    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    3.1174   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8234    2.3429   -0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349    1.0149   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    0.0336   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772    0.0304   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.0210   -2.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    0.0902   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4156    1.1070    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7836    1.0815    0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5826    0.0022    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9402   -0.0088    0.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071   -1.0513   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -1.0057   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469   -2.5587   -0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -4.1513   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6161   -3.3850    1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -2.6790    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -2.5967   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255    0.9960    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8577    3.2573    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408    4.1022   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572    2.6631   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675    1.9615    0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043    1.9001    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5874    0.3524    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203   -1.9510   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -1.8707   -1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  3  2  0
 20 14  1  0
 10  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.187  -0.692   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.235  -3.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.217  -1.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.741  -3.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.772  -4.445   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.143  -0.188   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   14                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   15                                                       
CONECT    7    9   11                                                       
CONECT    8   10   11                                                       
CONECT    9    7   12                                                       
CONECT   10    8   12                                                       
CONECT   11    7    8   17                                                  
CONECT   12    9   10   18                                                  
CONECT   13    5   15   16                                                  
CONECT   14    2   16   20                                                  
CONECT   15    6   13   20                                                  
CONECT   16   13   14   17                                                  
CONECT   17   11   16   19                                                  
CONECT   18   12                                                            
CONECT   19   17                                                            
CONECT   20   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0248975
HETATM    1  C1  UNL     1      -2.031  -3.280   0.282  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.800  -2.432   0.764  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.348  -1.066   0.545  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.491  -0.629   1.040  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.784   0.602   0.669  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.892   1.340   0.896  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.016   2.650   0.338  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.909   3.117  -0.422  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.823   2.343  -0.619  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.735   1.015  -0.087  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.815   0.034  -0.212  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.477   0.030  -0.865  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.454   0.021  -2.107  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.826   0.090  -0.288  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.416   1.107   0.371  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.784   1.081   0.715  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.583   0.002   0.420  1.00  0.00           C  
HETATM   18  O3  UNL     1       5.940  -0.009   0.735  1.00  0.00           O  
HETATM   19  C16 UNL     1       4.007  -1.051  -0.209  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.659  -1.006  -0.567  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.647  -2.559  -0.336  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.815  -4.151  -0.290  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.616  -3.385   1.192  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.377  -2.679   1.683  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.045  -2.597  -0.070  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.726   0.996   1.483  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.858   3.257   0.527  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.041   4.102  -0.823  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.957   2.663  -1.252  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.867   1.961   0.651  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.304   1.900   1.231  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.587   0.352   0.004  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.620  -1.951  -0.433  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.202  -1.871  -1.007  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   11   11
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   20
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   19
CONECT   18   32
CONECT   19   20   20   33
CONECT   20   34
END

HMDB0248975
     RDKit          3D
Benzarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -2.0313   -3.2803    0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997   -2.4323    0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479   -1.0662    0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4913   -0.6286    1.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844    0.6017    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8922    1.3399    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    2.6505    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    3.1174   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8234    2.3429   -0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349    1.0149   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    0.0336   -0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772    0.0304   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    0.0210   -2.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    0.0902   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4156    1.1070    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7836    1.0815    0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5826    0.0022    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9402   -0.0088    0.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071   -1.0513   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6591   -1.0057   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469   -2.5587   -0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -4.1513   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6161   -3.3850    1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769   -2.6790    1.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453   -2.5967   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255    0.9960    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8577    3.2573    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408    4.1022   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572    2.6631   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675    1.9615    0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043    1.9001    1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5874    0.3524    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203   -1.9510   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -1.8707   -1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  3  2  0
 20 14  1  0
 10  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Ethyl-3-(4-hydroxybenzoyl)benzofuran	Kegg
EHBB	MeSH
Benzaron	MeSH

Chemical Formula

C₁₇H₁₄O₃

Average Molecular Weight

266.296

Monoisotopic Molecular Weight

266.094294311

IUPAC Name

4-(2-ethyl-1-benzofuran-3-carbonyl)phenol

Traditional Name

benzarone

CAS Registry Number

Not Available

SMILES

CCC1=C(C(=O)C2=CC=C(O)C=C2)C2=CC=CC=C2O1

InChI Identifier

InChI=1S/C17H14O3/c1-2-14-16(13-5-3-4-6-15(13)20-14)17(19)11-7-9-12(18)10-8-11/h3-10,18H,2H2,1H3

InChI Key

RFRXIWQYSOIBDI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Benzofuran
3-aroylfuran
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzofurans (CHEBI:34559 )

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	4.25	ALOGPS
logP	4.01	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.13 m³·mol⁻¹	ChemAxon
Polarizability	28.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	161.783	30932474
DeepCCS	[M-H]-	159.425	30932474
DeepCCS	[M-2H]-	192.311	30932474
DeepCCS	[M+Na]+	167.876	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	165.7	32859911
AllCCS	[M+Na]+	166.7	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	165.8	32859911
AllCCS	[M+HCOO]-	165.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzarone	CCC1=C(C(=O)C2=CC=C(O)C=C2)C2=CC=CC=C2O1	3217.2	Standard polar	33892256
Benzarone	CCC1=C(C(=O)C2=CC=C(O)C=C2)C2=CC=CC=C2O1	2417.4	Standard non polar	33892256
Benzarone	CCC1=C(C(=O)C2=CC=C(O)C=C2)C2=CC=CC=C2O1	2515.3	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 - Benzarone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fka-3590000000-ac0be4cab465d600ab37	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzarone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzarone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzarone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Benzarone 10V, Positive-QTOF	splash10-014i-0390000000-9531e67851122bce3a4f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 20V, Positive-QTOF	splash10-00di-0930000000-96534d98af12e0f50104	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 40V, Positive-QTOF	splash10-05bf-9600000000-983fda8cc5f4c2017ea6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 10V, Negative-QTOF	splash10-014i-0190000000-7f8b1e2dc59525996c63	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 20V, Negative-QTOF	splash10-014i-1490000000-81f8a172a13ea0a174ae	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 40V, Negative-QTOF	splash10-0007-4910000000-817dfc3118c96edc6897	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 10V, Positive-QTOF	splash10-014i-0290000000-55f864082fc4c776e71d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 20V, Positive-QTOF	splash10-00di-4900000000-6d6ba14d5858fcfb3634	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 40V, Positive-QTOF	splash10-0596-7900000000-2386fb2a9d6b88942c73	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 10V, Negative-QTOF	splash10-014i-0090000000-b69facf5c5f0a18961c5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 20V, Negative-QTOF	splash10-014i-0390000000-b9d080519f78d02d03a0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzarone 40V, Negative-QTOF	splash10-0006-7790000000-39fdf93195e3be6e75c3	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

224468

KEGG Compound ID

C14474

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

255968

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 Benzarone (HMDB0248975)

MOL for HMDB0248975 (Benzarone)

3D MOL for HMDB0248975 (Benzarone)

3D SDF for HMDB0248975 (Benzarone)

3D-SDF for HMDB0248975 (Benzarone)

PDB for HMDB0248975 (Benzarone)

3D PDB for HMDB0248975 (Benzarone)

SMILES for HMDB0248975 (Benzarone)

INCHI for HMDB0248975 (Benzarone)

Structure for HMDB0248975 (Benzarone)

3D Structure for HMDB0248975 (Benzarone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra