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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:24:33 UTC

Update Date

2021-09-26 22:53:44 UTC

HMDB ID

HMDB0245327

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bisphenol B

Description

Bisphenol B belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). Based on a literature review a significant number of articles have been published on Bisphenol B. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bisphenol b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bisphenol B 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

HMDB0245327
     RDKit          3D
Bisphenol B
 36 37  0  0  0  0  0  0  0  0999 V2000
    1.1141   -2.8159   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -1.9111   -1.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2757   -0.9200    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -1.7268    1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410    0.0391   -0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.1463   -1.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    1.0808   -1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    1.9217   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277    2.8614   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    1.8287    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7768    0.8948    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9703   -0.1561    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4961    0.5203   -0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6650    1.2432   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    1.2746    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    2.0190    0.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.6018    1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946   -0.1108    1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627   -2.3661    0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6768   -3.7648   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -3.0165   -1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -1.4211   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -2.5181   -1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -2.5393    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507   -2.2670    1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -1.1340    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997   -0.5182   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071    1.1885   -2.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    3.7959   -1.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091    2.5058    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3554    0.8671    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169    0.4979   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0727    1.7723   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405    2.0953    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    0.6654    2.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923   -0.6342    2.3880 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv1572004221603132D          

 18 19  0  0  0  0            999 V2000
   -0.9059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245327

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O2/c1-3-16(2,12-4-8-14(17)9-5-12)13-6-10-15(18)11-7-13/h4-11,17-18H,3H2,1-2H3

> <INCHI_KEY>
HTVITOHKHWFJKO-UHFFFAOYSA-N

> <FORMULA>
C16H18O2

> <MOLECULAR_WEIGHT>
242.318

> <EXACT_MASS>
242.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.249058352440358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(4-hydroxyphenyl)butan-2-yl]phenol

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
4.489544081

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.378754564118331

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.77031603565891

> <JCHEM_PKA_STRONGEST_BASIC>
-5.461267439054095

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
83.87610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisphenol B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245327
     RDKit          3D
Bisphenol B
 36 37  0  0  0  0  0  0  0  0999 V2000
    1.1141   -2.8159   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -1.9111   -1.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2757   -0.9200    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -1.7268    1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410    0.0391   -0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.1463   -1.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    1.0808   -1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    1.9217   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277    2.8614   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    1.8287    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7768    0.8948    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9703   -0.1561    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4961    0.5203   -0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6650    1.2432   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    1.2746    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    2.0190    0.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.6018    1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946   -0.1108    1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627   -2.3661    0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6768   -3.7648   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -3.0165   -1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -1.4211   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -2.5181   -1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -2.5393    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507   -2.2670    1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -1.1340    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997   -0.5182   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071    1.1885   -2.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    3.7959   -1.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091    2.5058    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3554    0.8671    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169    0.4979   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0727    1.7723   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405    2.0953    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    0.6654    2.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923   -0.6342    2.3880 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  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      -1.691  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.541   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.461   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   16                                                            
CONECT    3    1   16                                                       
CONECT    4    8   12                                                       
CONECT    5    9   12                                                       
CONECT    6   10   13                                                       
CONECT    7   11   13                                                       
CONECT    8    4   14                                                       
CONECT    9    5   14                                                       
CONECT   10    6   15                                                       
CONECT   11    7   15                                                       
CONECT   12    4    5   16                                                  
CONECT   13    6    7   16                                                  
CONECT   14    8    9   17                                                  
CONECT   15   10   11   18                                                  
CONECT   16    2    3   12   13                                             
CONECT   17   14                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0245327
HETATM    1  C1  UNL     1       1.114  -2.816  -0.542  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.001  -1.911  -1.029  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.276  -0.920   0.082  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.687  -1.727   1.284  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.341   0.039  -0.272  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.931   0.146  -1.511  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.928   1.081  -1.760  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.338   1.922  -0.746  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.328   2.861  -0.964  1.00  0.00           O  
HETATM   10  C9  UNL     1      -2.759   1.829   0.498  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.777   0.895   0.713  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.970  -0.156   0.305  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.496   0.520  -0.778  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.665   1.243  -0.590  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.271   1.275   0.649  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.439   2.019   0.765  1.00  0.00           O  
HETATM   17  C15 UNL     1       2.745   0.602   1.720  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.595  -0.111   1.539  1.00  0.00           C  
HETATM   19  H1  UNL     1       1.663  -2.366   0.332  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.677  -3.765  -0.147  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.874  -3.017  -1.309  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.364  -1.421  -1.947  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.903  -2.518  -1.229  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.406  -2.539   0.970  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.151  -2.267   1.760  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.235  -1.134   2.043  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.600  -0.518  -2.294  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.407   1.189  -2.715  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.137   3.796  -1.280  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.109   2.506   1.266  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.355   0.867   1.712  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.017   0.498  -1.764  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.073   1.772  -1.445  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.941   2.095   1.623  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.271   0.665   2.674  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.192  -0.634   2.388  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    5   12
CONECT    4   24   25   26
CONECT    5    6    6   11
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   11   30
CONECT   11   31
CONECT   12   13   13   18
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   17
CONECT   16   34
CONECT   17   18   18   35
CONECT   18   36
END

HMDB0245327
     RDKit          3D
Bisphenol B
 36 37  0  0  0  0  0  0  0  0999 V2000
    1.1141   -2.8159   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -1.9111   -1.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2757   -0.9200    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -1.7268    1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410    0.0391   -0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.1463   -1.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    1.0808   -1.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    1.9217   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277    2.8614   -0.9635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    1.8287    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7768    0.8948    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9703   -0.1561    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4961    0.5203   -0.7782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6650    1.2432   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    1.2746    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4393    2.0190    0.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451    0.6018    1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946   -0.1108    1.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627   -2.3661    0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6768   -3.7648   -0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -3.0165   -1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -1.4211   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -2.5181   -1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -2.5393    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1507   -2.2670    1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -1.1340    2.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997   -0.5182   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071    1.1885   -2.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    3.7959   -1.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091    2.5058    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3554    0.8671    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0169    0.4979   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0727    1.7723   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405    2.0953    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2708    0.6654    2.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1923   -0.6342    2.3880 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 11  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Dihydroxy-2,2-diphenylbutane	Kegg
2,2-Bis(4-hydroxyphenyl)butane	Kegg

Chemical Formula

C₁₆H₁₈O₂

Average Molecular Weight

242.318

Monoisotopic Molecular Weight

242.13067982

IUPAC Name

4-[2-(4-hydroxyphenyl)butan-2-yl]phenol

Traditional Name

bisphenol B

CAS Registry Number

Not Available

SMILES

CCC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H18O2/c1-3-16(2,12-4-8-14(17)9-5-12)13-6-10-15(18)11-7-13/h4-11,17-18H,3H2,1-2H3

InChI Key

HTVITOHKHWFJKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Bisphenols

Alternative Parents

Substituents

Bisphenol
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

bisphenol (CHEBI:34581 )

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	4.24	ALOGPS
logP	4.49	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.77	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.88 m³·mol⁻¹	ChemAxon
Polarizability	27.25 Å³	ChemAxon
Number of Rings	2	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]+	165.527	30932474
DeepCCS	[M-H]-	163.169	30932474
DeepCCS	[M-2H]-	196.055	30932474
DeepCCS	[M+Na]+	171.62	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.1	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	161.0	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.9749 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2292.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	449.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	897.8 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	655.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1489.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	576.4 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	1488.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	483.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	467.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	390.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	220.2 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	14.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisphenol B	CCC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	3610.4	Standard polar	33892256
Bisphenol B	CCC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2232.9	Standard non polar	33892256
Bisphenol B	CCC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2252.0	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 - Bisphenol B GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-4690000000-e7cd0dcdf58080adfd50	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol B GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol B GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol B GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol B GC-MS (TBDMS_2_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 - Bisphenol B 10V, Positive-QTOF	splash10-0006-0090000000-7e460c9203309630f1ce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 20V, Positive-QTOF	splash10-0006-0290000000-2c269cbd03fecdcd25e2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 40V, Positive-QTOF	splash10-004j-0940000000-1469201fe707922e90fd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 10V, Negative-QTOF	splash10-0006-0090000000-f4e0751a2f38cbc93278	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 20V, Negative-QTOF	splash10-0006-0090000000-e8c8ff6cb208018d870b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 40V, Negative-QTOF	splash10-0006-7590000000-483206609a4c7c5d5aaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 10V, Positive-QTOF	splash10-0006-0390000000-65938c50d29bd51dbcfe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 20V, Positive-QTOF	splash10-0002-1910000000-5a096590fae1a92ee4ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 40V, Positive-QTOF	splash10-003g-1900000000-c76ec8f49976739d8754	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 10V, Negative-QTOF	splash10-0006-0090000000-9e49a0bb5f37da970e18	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 20V, Negative-QTOF	splash10-01ox-0290000000-68833e18f83d4c62afa0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol B 40V, Negative-QTOF	splash10-014l-3920000000-0e3784b00b7844afb2e2	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

59553

KEGG Compound ID

C14225

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66166

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 Bisphenol B (HMDB0245327)

MOL for HMDB0245327 (Bisphenol B)

3D MOL for HMDB0245327 (Bisphenol B)

3D SDF for HMDB0245327 (Bisphenol B)

3D-SDF for HMDB0245327 (Bisphenol B)

PDB for HMDB0245327 (Bisphenol B)

3D PDB for HMDB0245327 (Bisphenol B)

SMILES for HMDB0245327 (Bisphenol B)

INCHI for HMDB0245327 (Bisphenol B)

Structure for HMDB0245327 (Bisphenol B)

3D Structure for HMDB0245327 (Bisphenol B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra