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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:27:35 UTC

Update Date

2021-09-26 22:59:35 UTC

HMDB ID

HMDB0248996

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benziodarone

Description

Benziodarone, also known as amplivix, 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. Benziodarone is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Benziodarone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benziodarone 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

HMDB0248996
     RDKit          3D
Benziodarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -1.4176   -3.3502   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -2.3116   -1.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -0.9795   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365   -0.4459    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748    0.7365    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.6820    1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0359    2.9014    1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    3.1528    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867    2.2725    0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    1.0586    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -0.0577   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -0.0428   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354    0.1158   -2.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -0.1429   -0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9408   -0.8894    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.8346    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8583   -1.9983    2.5154 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325   -0.0631    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -0.0010    0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    0.6772   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2084    1.9323   -1.8674 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310    0.6376   -1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -3.2288   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498   -3.3720    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6246   -4.3430   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962   -2.3536   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -2.7005   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934    1.4503    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5960    3.6319    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    4.1040    1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    2.4446    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195   -1.5140    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137    0.6144    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833    1.2171   -2.1427 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  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  3  2  0
 22 14  1  0
 10  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 15 32  1  0
 19 33  1  0
 22 34  1  0
M  END

  Mrv1572004221605072D          

 22 24  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
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    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
   -0.9851   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.3409    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
   -1.5371   -0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -1.8414    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342    0.9540    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -0.6152    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  2  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  2  1  0  0  0  0
 14  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  1  0  0  0  0
 22 13  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248996

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H12I2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3

> <INCHI_KEY>
CZCHIEJNWPNBDE-UHFFFAOYSA-N

> <FORMULA>
C17H12I2O3

> <MOLECULAR_WEIGHT>
518.089

> <EXACT_MASS>
517.88758

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
39.83624536372787

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-ethyl-1-benzofuran-3-carbonyl)-2,6-diiodophenol

> <ALOGPS_LOGP>
5.80

> <JCHEM_LOGP>
5.868129606999999

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.606140270090533

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9834082926931744

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
103.8542

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benziodarone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248996
     RDKit          3D
Benziodarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -1.4176   -3.3502   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -2.3116   -1.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -0.9795   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365   -0.4459    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748    0.7365    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.6820    1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0359    2.9014    1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    3.1528    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867    2.2725    0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    1.0586    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -0.0577   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -0.0428   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354    0.1158   -2.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -0.1429   -0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9408   -0.8894    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.8346    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8583   -1.9983    2.5154 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325   -0.0631    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -0.0010    0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    0.6772   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2084    1.9323   -1.8674 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310    0.6376   -1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -3.2288   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498   -3.3720    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6246   -4.3430   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962   -2.3536   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -2.7005   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934    1.4503    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5960    3.6319    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    4.1040    1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    2.4446    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195   -1.5140    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137    0.6144    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833    1.2171   -2.1427 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  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  3  2  0
 22 14  1  0
 10  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 15 32  1  0
 19 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-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      -0.333  -1.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.887   0.957   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.839  -1.973   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.393   0.636   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.869  -0.828   0.000  0.00  0.00           C+0
HETATM   18  I   UNK     0      -2.315  -3.437   0.000  0.00  0.00           I+0
HETATM   19  I   UNK     0      -3.424   1.781   0.000  0.00  0.00           I+0
HETATM   20  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.376  -1.148   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   13                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   14                                                       
CONECT    7    9   11                                                       
CONECT    8    9   12                                                       
CONECT    9    7    8   16                                                  
CONECT   10    5   14   15                                                  
CONECT   11    7   17   18                                                  
CONECT   12    8   17   19                                                  
CONECT   13    2   15   22                                                  
CONECT   14    6   10   22                                                  
CONECT   15   10   13   16                                                  
CONECT   16    9   15   20                                                  
CONECT   17   11   12   21                                                  
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0248996
HETATM    1  C1  UNL     1      -1.418  -3.350  -0.307  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.110  -2.312  -1.189  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.106  -0.979  -0.570  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.136  -0.446   0.075  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.875   0.736   0.532  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.574   1.682   1.252  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.036   2.901   1.627  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.749   3.153   1.252  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.987   2.272   0.542  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.574   1.059   0.187  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.095  -0.058  -0.528  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.198  -0.043  -1.141  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.135   0.116  -2.462  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.533  -0.143  -0.649  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.941  -0.889   0.444  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.280  -0.835   0.870  1.00  0.00           C  
HETATM   17  I1  UNL     1       3.858  -1.998   2.515  1.00  0.00           I  
HETATM   18  C15 UNL     1       4.233  -0.063   0.244  1.00  0.00           C  
HETATM   19  O3  UNL     1       5.548  -0.001   0.669  1.00  0.00           O  
HETATM   20  C16 UNL     1       3.830   0.677  -0.848  1.00  0.00           C  
HETATM   21  I2  UNL     1       5.208   1.932  -1.867  1.00  0.00           I  
HETATM   22  C17 UNL     1       2.531   0.638  -1.276  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.332  -3.229  -0.222  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.950  -3.372   0.667  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.625  -4.343  -0.809  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.696  -2.354  -2.206  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.153  -2.701  -1.288  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.593   1.450   1.533  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.596   3.632   2.194  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.316   4.104   1.560  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.009   2.445   0.237  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.219  -1.514   0.931  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.214   0.614   0.173  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.183   1.217  -2.143  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   11   11
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   22
CONECT   15   16   32
CONECT   16   17   18   18
CONECT   18   19   20
CONECT   19   33
CONECT   20   21   22   22
CONECT   22   34
END

HMDB0248996
     RDKit          3D
Benziodarone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -1.4176   -3.3502   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -2.3116   -1.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -0.9795   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365   -0.4459    0.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748    0.7365    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.6820    1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0359    2.9014    1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    3.1528    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867    2.2725    0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738    1.0586    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -0.0577   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -0.0428   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354    0.1158   -2.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -0.1429   -0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9408   -0.8894    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.8346    0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8583   -1.9983    2.5154 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325   -0.0631    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -0.0010    0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    0.6772   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2084    1.9323   -1.8674 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310    0.6376   -1.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -3.2288   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498   -3.3720    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6246   -4.3430   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6962   -2.3536   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -2.7005   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934    1.4503    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5960    3.6319    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3157    4.1040    1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    2.4446    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195   -1.5140    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137    0.6144    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833    1.2171   -2.1427 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  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  3  2  0
 22 14  1  0
 10  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 15 32  1  0
 19 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Amplivix	Kegg
Dilafurane	MeSH
Cardivix	MeSH
2-Ethyl-3-benzofuranyl-4-hydroxy-3,5-diiodophenyl ketone	MeSH
Algocor	MeSH
Dila-vasal	MeSH
Sanofi synthelabo brand OF benziodarone	MeSH

Chemical Formula

C₁₇H₁₂I₂O₃

Average Molecular Weight

518.089

Monoisotopic Molecular Weight

517.88758

IUPAC Name

4-(2-ethyl-1-benzofuran-3-carbonyl)-2,6-diiodophenol

Traditional Name

benziodarone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H12I2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3

InChI Key

CZCHIEJNWPNBDE-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
2-iodophenol
2-halophenol
Phenol
Iodobenzene
Halobenzene
Aryl halide
Aryl iodide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organoiodide
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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 (HMDB: HMDB0248996)

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	5.8	ALOGPS
logP	5.87	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.61	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.85 m³·mol⁻¹	ChemAxon
Polarizability	39.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	191.709	30932474
DeepCCS	[M-H]-	189.235	30932474
DeepCCS	[M-2H]-	223.559	30932474
DeepCCS	[M+Na]+	199.014	30932474
AllCCS	[M+H]+	199.3	32859911
AllCCS	[M+H-H2O]+	196.8	32859911
AllCCS	[M+NH4]+	201.5	32859911
AllCCS	[M+Na]+	202.2	32859911
AllCCS	[M-H]-	178.3	32859911
AllCCS	[M+Na-2H]-	178.8	32859911
AllCCS	[M+HCOO]-	179.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benziodarone	CCC1=C(C(=O)C2=CC(I)=C(O)C(I)=C2)C2=CC=CC=C2O1	3920.0	Standard polar	33892256
Benziodarone	CCC1=C(C(=O)C2=CC(I)=C(O)C(I)=C2)C2=CC=CC=C2O1	3120.5	Standard non polar	33892256
Benziodarone	CCC1=C(C(=O)C2=CC(I)=C(O)C(I)=C2)C2=CC=CC=C2O1	3016.3	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 - Benziodarone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benziodarone 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 - Benziodarone 10V, Positive-QTOF	splash10-014i-0103090000-5d10669b025f9147311b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 20V, Positive-QTOF	splash10-00di-0409040000-f3aa63fef50728d86eda	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 40V, Positive-QTOF	splash10-00dl-1209000000-7b2a4303d58bc3e9119b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 10V, Negative-QTOF	splash10-014i-0000090000-0890e07d3d982c1c0a2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 20V, Negative-QTOF	splash10-014i-0204190000-e2e86d0d3ab2714d753e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 40V, Negative-QTOF	splash10-0006-3914100000-fa2876e6d67e96b7e228	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 10V, Positive-QTOF	splash10-014i-0000090000-1e76f8ca870c0a6fad8a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 20V, Positive-QTOF	splash10-00xr-0108090000-9c3da0879a8c0e4625c8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 40V, Positive-QTOF	splash10-00dl-1409000000-c02eb8ee746bde5762f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 10V, Negative-QTOF	splash10-014i-0000090000-bc7b47381e7174ce7529	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 20V, Negative-QTOF	splash10-014i-0400090000-82fd46153ef2ac5fc645	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benziodarone 40V, Negative-QTOF	splash10-004i-0900000000-0dba40d354fa6a5575e0	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

DB13277

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benziodarone

METLIN ID

Not Available

PubChem Compound

6237

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 Benziodarone (HMDB0248996)

MOL for HMDB0248996 (Benziodarone)

3D MOL for HMDB0248996 (Benziodarone)

3D SDF for HMDB0248996 (Benziodarone)

3D-SDF for HMDB0248996 (Benziodarone)

PDB for HMDB0248996 (Benziodarone)

3D PDB for HMDB0248996 (Benziodarone)

SMILES for HMDB0248996 (Benziodarone)

INCHI for HMDB0248996 (Benziodarone)

Structure for HMDB0248996 (Benziodarone)

3D Structure for HMDB0248996 (Benziodarone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra