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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:48:03 UTC

Update Date

2022-03-07 02:53:15 UTC

HMDB ID

HMDB0032133

Secondary Accession Numbers

HMDB32133

Metabolite Identification

Common Name

Bisphenol A

Description

Bisphenol A, commonly abbreviated as BPA, is an organic compound with two phenol functional groups. It is a difunctional building block of several important plastics and plastic additives. With an annual production of 2–3 million metric tonnes, it is an important monomer in the production of polycarbonate. It is a potential food contaminant arising from its use in reusable polycarbonate food containers such as water carboys, baby bottles and kitchen utensils

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0032133
     RDKit          3D
Bisphenol A
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.1953   -2.3185    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0047   -0.9478   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -1.1720   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955   -0.0960   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.6074    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4169    0.1020    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5420    1.3724    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7041    2.1093    0.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    1.8909   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    1.1549   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275   -0.3735    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -0.2652    1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.2905    1.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279    0.7540    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8249    1.3162    1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3749    0.6369   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1974    0.0839   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7808   -2.8610   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -2.8481   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983   -2.1549    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -1.7875   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -1.7439   -2.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603   -0.2288   -2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2171   -1.5973    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -0.3035    1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4484    1.9975   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799    2.8897   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378    1.5963   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001   -0.6233    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8274    0.3744    2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821    2.3331    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    1.0004   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    0.0262   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10  4  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END


  Mrv1652305271900042D          

 17 18  0  0  0  0            999 V2000
   -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
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032133

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3

> <INCHI_KEY>
IISBACLAFKSPIT-UHFFFAOYSA-N

> <FORMULA>
C15H16O2

> <MOLECULAR_WEIGHT>
228.2863

> <EXACT_MASS>
228.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.405321646558264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
4.044975416000001

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.387640214449602

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.77935587234571

> <JCHEM_PKA_STRONGEST_BASIC>
-5.460166327133153

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
79.27510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisphenol-A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032133
     RDKit          3D
Bisphenol A
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.1953   -2.3185    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0047   -0.9478   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -1.1720   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955   -0.0960   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.6074    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4169    0.1020    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5420    1.3724    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7041    2.1093    0.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    1.8909   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    1.1549   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275   -0.3735    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -0.2652    1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.2905    1.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279    0.7540    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8249    1.3162    1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3749    0.6369   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1974    0.0839   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7808   -2.8610   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -2.8481   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983   -2.1549    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -1.7875   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -1.7439   -2.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603   -0.2288   -2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2171   -1.5973    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -0.3035    1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4484    1.9975   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799    2.8897   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378    1.5963   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001   -0.6233    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8274    0.3744    2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821    2.3331    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    1.0004   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    0.0262   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10  4  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -5.541   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.461   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    9   12                                                       
CONECT    6   10   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   13                                                       
CONECT    9    5   14                                                       
CONECT   10    6   14                                                       
CONECT   11    3    4   15                                                  
CONECT   12    5    6   15                                                  
CONECT   13    7    8   16                                                  
CONECT   14    9   10   17                                                  
CONECT   15    1    2   11   12                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0032133
HETATM    1  C1  UNL     1      -0.195  -2.318   0.166  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.005  -0.948  -0.461  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.197  -1.172  -1.941  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.195  -0.096  -0.285  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.246  -0.607   0.450  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.417   0.102   0.682  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.542   1.372   0.160  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.704   2.109   0.376  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.478   1.891  -0.584  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.331   1.155  -0.793  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.228  -0.374   0.107  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.462  -0.265   1.458  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.645   0.290   1.883  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.628   0.754   1.033  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.825   1.316   1.514  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.375   0.637  -0.313  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.197   0.084  -0.759  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.781  -2.861  -0.004  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.054  -2.848  -0.275  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.298  -2.155   1.265  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.651  -1.787  -2.368  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.124  -1.744  -2.167  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.160  -0.229  -2.523  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.217  -1.597   0.889  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.244  -0.304   1.261  1.00  0.00           H  
HETATM   26  H9  UNL     1      -5.448   1.997  -0.323  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.580   2.890  -0.993  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.538   1.596  -1.373  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.700  -0.623   2.145  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.827   0.374   2.964  1.00  0.00           H  
HETATM   31  H14 UNL     1       4.782   2.333   1.658  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.145   1.000  -0.999  1.00  0.00           H  
HETATM   33  H16 UNL     1       2.068   0.026  -1.853  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   11
CONECT    3   21   22   23
CONECT    4    5    5   10
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8    9
CONECT    8   26
CONECT    9   10   10   27
CONECT   10   28
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   16
CONECT   15   31
CONECT   16   17   17   32
CONECT   17   33
END

HMDB0032133
     RDKit          3D
Bisphenol A
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.1953   -2.3185    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0047   -0.9478   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -1.1720   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1955   -0.0960   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.6074    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4169    0.1020    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5420    1.3724    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7041    2.1093    0.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    1.8909   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    1.1549   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275   -0.3735    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -0.2652    1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.2905    1.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279    0.7540    1.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8249    1.3162    1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3749    0.6369   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1974    0.0839   -0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7808   -2.8610   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -2.8481   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983   -2.1549    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -1.7875   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -1.7439   -2.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603   -0.2288   -2.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2171   -1.5973    0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -0.3035    1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4484    1.9975   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799    2.8897   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378    1.5963   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001   -0.6233    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8274    0.3744    2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821    2.3331    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    1.0004   -0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676    0.0262   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10  4  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2, 2-Bis(4-hydroxyphenyl)propane	ChEBI
2,2-Bis(4'-hydroxyphenyl)propane	ChEBI
2,2-Bis(4-hydroxyphenyl)propane	ChEBI
2,2-Bis(p-hydroxyphenyl)propane	ChEBI
2,2-Di(4-hydroxyphenyl)propane	ChEBI
2,2-Di(4-phenylol)propane	ChEBI
4,4'-(1-Methylethane-1,1-diyl)diphenol	ChEBI
4,4'-(1-Methylethylidene)bisphenol	ChEBI
4,4'-(Propane-2,2-diyl)diphenol	ChEBI
4,4'-Bisphenol a	ChEBI
4,4'-Isopropylidenediphenol	ChEBI
Bisphenol-a	ChEBI
BPA	ChEBI
Dianin's compound	ChEBI
(1-Methylethylidene)bis-phenol	HMDB
1,1'-(1-Methylethylidene)bisphenylol, 9ci	HMDB
2, 2-Bis(hydroxyphenyl)propane	HMDB
2, 2-Di(4-phenylol)propane	HMDB
2,2'-Bis(4-hydroxyphenyl)propane	HMDB
2,2-(4,4'-Dihydroxydiphenyl)propane	HMDB
2,2-(4,4-Dihydroxydiphenyl)propane	HMDB
2,2-Bis (4-hydroxyphenol) propane	HMDB
2,2-Bis(4,4'-hydroxyphenyl)propane	HMDB
2,2-Bis(hydroxyphenyl)propane	HMDB
2,2-Bis(p-hydroxyphenyl)-propane	HMDB
2,2-Bis-4'-hydroxyfenylpropan	HMDB
2,2-Bis[4-hydroxyphenyl]propane	HMDB
2,2-Di-(4'-hydroxyphenyl)-propane	HMDB
4, 4'-Bisphenol a	HMDB
4, 4'-Dihydroxydiphenyl-2,2-propane	HMDB
4, 4'-Dihydroxydiphenyldimethylmethane	HMDB
4, 4'-Dihydroxydiphenylpropane	HMDB
4,4' Isopropylidinediphenol	HMDB
4,4'-(1-Methylethylidene)bis-phenol	HMDB
4,4'-(1-Methylethylidene)bisphenol, 9ci	HMDB
4,4'-Dihydroxdiphenylpropane	HMDB
4,4'-Dihydroxy-2,2-diphenylpropane	HMDB
4,4'-Dihydroxydiphenyl-2,2-propane	HMDB
4,4'-Dihydroxydiphenyldimethylmethane	HMDB
4,4'-Dihydroxydiphenylpropane	HMDB
4,4'-Dimethylmethylenedi-phenol	HMDB
4,4'-Dimethylmethylenediphenol	HMDB
4,4'-Isopropylidene diphenol	HMDB
4,4'-ISOPROPYLIDENE-diphenol	HMDB
4,4'-Isopropylidenebisphenol	HMDB
4,4'-Isopropylidenebis[phenol]	HMDB
4,4'-Isopropylidenedi-phenol	HMDB
4,4'-ISOPROPYLIDENEDIPHENOL (bisphenol a)	HMDB
4,4'-Isopropylidenediphenol b	HMDB
4,4'-Isopropylidenediphenol, 8ci	HMDB
4,4'-Propane-2,2-diyldiphenol	HMDB
4,4-Isopropylidenediphenol	HMDB
4,4[-Isopropylidenediphenol	HMDB
4-[1-(4-Hydroxyphenyl)-1-methylethyl]phenol	HMDB
beta, Beta'-bis(p-hydroxyphenyl)propane	HMDB
beta,Beta'-bis(p-hydroxyphenyl)propane	HMDB
beta,beta-Di-(p-hydroxyphenyl)propane	HMDB
beta-Di-(p-hydroxyphenyl)propane	HMDB
beta-Di-p-hydroxyphenylpropane	HMDB
Biphenol a	HMDB
Bis(4-hyd roxyphenyl) dimethylmethane	HMDB
Bis(4-hydroxyphenyl) dimethylmethane	HMDB
Bis(4-hydroxyphenyl) propane	HMDB
Bis(4-hydroxyphenyl)dimethylmethane	HMDB
Bis(4-hydroxyphenyl)propane	HMDB
Bis(p-hydroxyphenyl)propane	HMDB
Bisferol a	HMDB
Bisphenol	HMDB
Bisphenol a (bpa)	HMDB
Bisphenol a, disodium salt	HMDB
Bisphenol a, sodium salt	HMDB
Bisphenol a.	HMDB
Di-2,2-(4-hydroxyphenyl)propane	HMDB
Dian	HMDB
Diano	HMDB
Dimethyl bis(p-hydroxyphenyl)methane	HMDB
Dimethylbis(p-hydroxyphenyl)methane	HMDB
Dimethylmethylene-p,p'-diphenol	HMDB
Diphenylolpropane	HMDB
Hydrogenated bisphenol a	HMDB
Ipognox 88	HMDB
Isopropylidenebis(4-hydroxybenzene)	HMDB
Millad hbpa	HMDB
Noname	HMDB
p, P'-dihydroxydiphenyldimethylmethane	HMDB
p, P'-dihydroxydiphenylpropane	HMDB
p, P'-isopropylidenediphenol	HMDB
p,P'-bisphenol a	HMDB
p,P'-dihydroxydiphenyldimethylmethane	HMDB
p,P'-dihydroxydiphenylpropane	HMDB
p,P'-isopropylidenebisphenol	HMDB
p,P'-isopropylidenediphenol	HMDB
Parabis	HMDB
Parabis a	HMDB
Poly(bisphenol a carbonate)	HMDB
Rikabanol	HMDB
Ucar bisphenol a	HMDB
Ucar bisphenol HP	HMDB

Chemical Formula

C₁₅H₁₆O₂

Average Molecular Weight

228.2863

Monoisotopic Molecular Weight

228.115029756

IUPAC Name

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

Traditional Name

bisphenol-A

CAS Registry Number

80-05-7

SMILES

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

InChI Identifier

InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3

InChI Key

IISBACLAFKSPIT-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:33216 )
Bisphenols (C13624 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0032133)

Biofluid or Excreta

Urine (HMDB: HMDB0032133)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0032133)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0032133)
Inhalation (HMDB: HMDB0032133)

Enteral

Ingestion (HMDB: HMDB0032133)

Source

Endogenous

Endogenous (HMDB: HMDB0032133)

Exogenous

Food

Food (HMDB: HMDB0032133)

Synthetic

Synthetic (HMDB: HMDB0032133)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0032133)

Biomarker

Bisphenol A Exposure (MarkerDB: MDB00029800)

Environmental role

Air pollutant (HMDB: HMDB0032133)

Biological role

xenoestrogen (HMDB: HMDB0032133)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156 - 157 °C	Not Available
Boiling Point	292.00 to 293.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.12 mg/mL at 25 °C	Not Available
LogP	3.32	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	147.126	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000915

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	3.81	ALOGPS
logP	4.04	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.78	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	2	ChemAxon
Refractivity	79.28 m³·mol⁻¹	ChemAxon
Polarizability	25.41 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
DarkChem	[M+H]+	153.281	31661259
DarkChem	[M-H]-	153.715	31661259
DeepCCS	[M+H]+	160.709	30932474
DeepCCS	[M-H]-	158.351	30932474
DeepCCS	[M-2H]-	191.237	30932474
DeepCCS	[M+Na]+	166.802	30932474
AllCCS	[M+H]+	150.9	32859911
AllCCS	[M+H-H2O]+	146.8	32859911
AllCCS	[M+NH4]+	154.8	32859911
AllCCS	[M+Na]+	156.0	32859911
AllCCS	[M-H]-	156.1	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	155.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisphenol A	CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	3617.7	Standard polar	33892256
Bisphenol A	CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2142.8	Standard non polar	33892256
Bisphenol A	CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2158.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bisphenol A,1TMS,isomer #1	CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1	2216.5	Semi standard non polar	33892256
Bisphenol A,2TMS,isomer #1	CC(C)(C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1	2197.8	Semi standard non polar	33892256
Bisphenol A,1TBDMS,isomer #1	CC(C)(C1=CC=C(O)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2491.4	Semi standard non polar	33892256
Bisphenol A,2TBDMS,isomer #1	CC(C)(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2713.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Bisphenol A EI-B (Non-derivatized)	splash10-03di-2290000000-5a53b16778a578ff5d0d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Bisphenol A EI-B (Non-derivatized)	splash10-03di-2290000000-5a53b16778a578ff5d0d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol A GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g0-1790000000-7521406d051aed77fe2f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol A GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-6289000000-59b1fac0d66836445629	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-3590000000-0cd99fd08fc2fad698f3	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOF	splash10-0zfs-4960000000-b4ebb7f1ff08fbb41adb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOF	splash10-004i-1090000000-80a2709d727e93053cd1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-c33246c7d9d8b300c90c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-e5f7d4cb43ef56a85056	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOF	splash10-0532-9340000000-c3298310f84ad87b1310	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOF	splash10-000t-9000000000-75784b9156574d6f1762	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A LC-ESI-ITFT , positive-QTOF	splash10-0a4j-1900000000-1316f0a328865698ba14	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A 75V, Positive-QTOF	splash10-000t-9000000000-75784b9156574d6f1762	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A 35V, Positive-QTOF	splash10-0zfs-4960000000-b4ebb7f1ff08fbb41adb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A 15V, Positive-QTOF	splash10-004i-0090000000-c33246c7d9d8b300c90c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A 30V, Positive-QTOF	splash10-004i-1090000000-80a2709d727e93053cd1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A 30V, Positive-QTOF	splash10-004i-0090000000-e5f7d4cb43ef56a85056	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A 45V, Positive-QTOF	splash10-0532-9340000000-c3298310f84ad87b1310	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bisphenol A 35V, Positive-QTOF	splash10-0a4j-1900000000-1316f0a328865698ba14	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 10V, Positive-QTOF	splash10-004i-0090000000-8791a2cf0310bf33a81e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 20V, Positive-QTOF	splash10-004i-0190000000-ee807d7dec5640d38d18	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 40V, Positive-QTOF	splash10-01rb-2920000000-e15c6a1d966dd429fe3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 10V, Negative-QTOF	splash10-004i-0090000000-0494eb6f9068e16e1d99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 20V, Negative-QTOF	splash10-004i-0090000000-e9b5452c25e607f29950	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 40V, Negative-QTOF	splash10-002f-9470000000-9d3d569c0a3f755f123f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 10V, Positive-QTOF	splash10-002r-1960000000-42e45d340eea8ee9e3db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 20V, Positive-QTOF	splash10-0a4i-3900000000-8ef860db11d71a8b2f2e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 40V, Positive-QTOF	splash10-0a4i-2900000000-61ebc2c60a263652b43e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 10V, Negative-QTOF	splash10-004i-3090000000-27243d7aedeaef4a196c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol A 20V, Negative-QTOF	splash10-0095-3940000000-3863b01420a8ec7c47d3	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

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	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.00142(0.00095-0.00202) umol/mmol creatinine	Not Available	Both	Normal	Report on Human B...	details
Urine	Detected and Quantified	0.00120(0.00095-0.00153) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Report on Human B...	details
Urine	Detected and Quantified	0.000941 (0.000872-0.00102) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Report on Human B... National Health a...	details
Urine	Detected and Quantified	0.00117 (0.00104-0.00131) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Report on Human B... National Health a...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06973

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008856

KNApSAcK ID

Not Available

Chemspider ID

6371

KEGG Compound ID

C13624

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bisphenol_A

METLIN ID

Not Available

PubChem Compound

6623

PDB ID

2OH

ChEBI ID

33216

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029800

Good Scents ID

rw1450961

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kim JY, Jeong HG: Down-regulation of inducible nitric oxide synthase and tumor necrosis factor-alpha expression by bisphenol A via nuclear factor-kappaB inactivation in macrophages. Cancer Lett. 2003 Jun 30;196(1):69-76. [PubMed:12860292 ]
Masuda S, Terashima Y, Sano A, Kuruto R, Sugiyama Y, Shimoi K, Tanji K, Yoshioka H, Terao Y, Kinae N: Changes in the mutagenic and estrogenic activities of bisphenol A upon treatment with nitrite. Mutat Res. 2005 Aug 1;585(1-2):137-46. [PubMed:15936980 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Bisphenol A (HMDB0032133)

MOL for HMDB0032133 (Bisphenol A)

3D MOL for HMDB0032133 (Bisphenol A)

3D SDF for HMDB0032133 (Bisphenol A)

3D-SDF for HMDB0032133 (Bisphenol A)

PDB for HMDB0032133 (Bisphenol A)

3D PDB for HMDB0032133 (Bisphenol A)

SMILES for HMDB0032133 (Bisphenol A)

INCHI for HMDB0032133 (Bisphenol A)

Structure for HMDB0032133 (Bisphenol A)

3D Structure for HMDB0032133 (Bisphenol A)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra