NP-MRD: Showing NP-Card for Tetrabromobisphenol A (NP0002796)

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Record Information

Version

1.0

Created at

2020-11-23 19:40:40 UTC

Updated at

2021-08-12 19:52:10 UTC

NP-MRD ID

NP0002796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetrabromobisphenol A

Provided By

BMRB

Description

Tetrabromobisphenol A is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2007 (PMID: 17784851). Based on a literature review a small amount of articles have been published on Tetrabromobisphenol A (PMID: 17984079) (PMID: 24060738) (PMID: 24709479) (PMID: 25042713).

Structure

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


     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    0.1095   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101   -0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0893    1.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5068    0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412   -1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379   -1.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724   -2.3141    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969    0.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3280    2.8706    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1691    1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866   -0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1489   -1.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6456   -1.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -2.9106    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4800   -0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9767   -0.4176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177    1.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6522    2.2741    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3210    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338   -1.7875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9812   -1.6736    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089   -3.0134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656    1.7424    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540    1.7475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1887    2.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9502   -1.9618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8314   -0.8689    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763    2.1613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561   -2.2013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8111    0.8289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588    2.4730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1 22  1  6
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  3 25  1  1
  3 26  1  0
  3 27  1  0
  5 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 18 32  1  0
 21 33  1  0
M  END

NP0002796
     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.4348   -1.7164    1.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100   -1.0517    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0781   -2.2100   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.3755    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465   -0.5388   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    0.1141   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356   -0.1516   -2.0875 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.6577    0.9703    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.6579    0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7345    1.1587    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.3231    2.8372 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5059    0.4877    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -0.1761   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3292    1.4516   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    2.2764   -1.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2864    0.9975    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697    1.4941    1.5153 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567    0.1987    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4932   -2.0436    1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -1.1096    2.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1660   -2.6664    1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376   -1.8719   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7213   -2.9241   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434   -1.1962   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5593    1.5219   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704    0.6264    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373    0.0365   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802    2.5111   -0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2332   -0.1526    1.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    0.1095   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101   -0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0893    1.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5068    0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412   -1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8379   -1.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724   -2.3141    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969    0.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3280    2.8706    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1691    1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3078   -2.9106    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4800   -0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6588    2.4730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  1  1
  4  5  2  0
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  3 27  1  0
  5 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 18 32  1  0
 21 33  1  0
M  END
> <DATABASE_ID>
NP0002796

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H12Br4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3

> <INCHI_KEY>
VEORPZCZECFIRK-UHFFFAOYSA-N

> <FORMULA>
C15H12Br4O2

> <MOLECULAR_WEIGHT>
543.871

> <EXACT_MASS>
539.757080216

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.924285595498276

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6-dibromo-4-[2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl]phenol

> <ALOGPS_LOGP>
6.57

> <JCHEM_LOGP>
7.119985917333333

> <ALOGPS_LOGS>
-6.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.181778900732154

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.574307492214067

> <JCHEM_PKA_STRONGEST_BASIC>
-7.379814332921378

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
109.7663

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.10e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrabromobisphenol A

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002796
     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.4348   -1.7164    1.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100   -1.0517    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0781   -2.2100   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.3755    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465   -0.5388   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    0.1141   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356   -0.1516   -2.0875 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.6577    0.9703    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.6579    0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7345    1.1587    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.3231    2.8372 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5059    0.4877    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -0.1761   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148    0.2980   -1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407    1.1047   -1.8757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652    1.7171   -3.6919 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    1.4516   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    2.2764   -1.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2864    0.9975    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697    1.4941    1.5153 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567    0.1987    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4932   -2.0436    1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -1.1096    2.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0376   -1.8719   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0425   -2.7613   -0.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213   -2.9241   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434   -1.1962   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5593    1.5219   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704    0.6264    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373    0.0365   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802    2.5111   -0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2332   -0.1526    1.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12  4  1  0
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  5 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 18 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0       4.001  -6.930   0.000  0.00  0.00          Br+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      -1.334   2.310   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   13                                             
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4                                                       
CONECT   13    2   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    NP0002796
HETATM    1  C1  UNL     1      -0.435  -1.716   1.614  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.110  -1.052   0.291  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.078  -2.210  -0.717  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.186  -0.376   0.288  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.146  -0.539  -0.709  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.365   0.114  -0.689  1.00  0.00           C  
HETATM    7 BR1  UNL     1       4.636  -0.152  -2.087  1.00  0.00          BR  
HETATM    8  C7  UNL     1       3.658   0.970   0.361  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.880   1.658   0.430  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.734   1.159   1.367  1.00  0.00           C  
HETATM   11 BR2  UNL     1       3.077   2.323   2.837  1.00  0.00          BR  
HETATM   12  C9  UNL     1       1.506   0.488   1.328  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.242  -0.176  -0.144  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.315   0.298  -1.442  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.341   1.105  -1.876  1.00  0.00           C  
HETATM   16 BR3  UNL     1      -2.365   1.717  -3.692  1.00  0.00          BR  
HETATM   17  C13 UNL     1      -3.329   1.452  -0.988  1.00  0.00           C  
HETATM   18  O2  UNL     1      -4.371   2.276  -1.447  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.286   0.997   0.307  1.00  0.00           C  
HETATM   20 BR4  UNL     1      -4.670   1.494   1.515  1.00  0.00          BR  
HETATM   21  C15 UNL     1      -2.257   0.199   0.710  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.493  -2.044   1.664  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.202  -1.110   2.490  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.166  -2.666   1.738  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.038  -1.872  -1.746  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.043  -2.761  -0.550  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.721  -2.924  -0.417  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.943  -1.196  -1.531  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.559   1.522  -0.304  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.770   0.626   2.106  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.537   0.037  -2.173  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.080   2.511  -0.771  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.233  -0.153   1.735  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4   13
CONECT    3   25   26   27
CONECT    4    5    5   12
CONECT    5    6   28
CONECT    6    7    8    8
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   12   12
CONECT   12   30
CONECT   13   14   14   21
CONECT   14   15   31
CONECT   15   16   17   17
CONECT   17   18   19
CONECT   18   32
CONECT   19   20   21   21
CONECT   21   33
END

NP0002796
     RDKit          3D

33 34  0  0  0  0  0  0  0  0999 V2000
   -0.4348   -1.7164    1.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100   -1.0517    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0781   -2.2100   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.3755    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465   -0.5388   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653    0.1141   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356   -0.1516   -2.0875 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.6577    0.9703    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.6579    0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7345    1.1587    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    2.3231    2.8372 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5059    0.4877    1.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -0.1761   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148    0.2980   -1.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407    1.1047   -1.8757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652    1.7171   -3.6919 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    1.4516   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    2.2764   -1.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2864    0.9975    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697    1.4941    1.5153 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567    0.1987    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4932   -2.0436    1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -1.1096    2.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1660   -2.6664    1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376   -1.8719   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0425   -2.7613   -0.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213   -2.9241   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434   -1.1962   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5593    1.5219   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704    0.6264    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373    0.0365   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0802    2.5111   -0.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2332   -0.1526    1.7351 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  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 12  4  1  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 18 32  1  0
 21 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
2,2',6,6'-Tetrabromobisphenol a	ChEBI
2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane	ChEBI
4,4'-(1-Methylethylidene)bis(2,6-dibromophenol)	ChEBI
4,4'-(2,2-Propanediyl) bis[2,6-dibromo]phenol	ChEBI
4,4'-Isopropylidenebis(2,6-dibromophenol)	ChEBI
Tetrabromobisphenol-a	ChEBI
3,3',5,5'-Tetrabromobisphenol a	Kegg
Bis(2,3-dibromopropylether)-2,2-bis(3,5-dibromo-4-(2,3-dibromopropoxy)phenyl)propane	MeSH
TBBPA CPD	MeSH

Chemical Formula

C₁₅H₁₂Br₄O₂

Average Mass

543.8710 Da

Monoisotopic Mass

539.75708 Da

IUPAC Name

2,6-dibromo-4-[2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl]phenol

Traditional Name

tetrabromobisphenol A

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H12Br4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3

InChI Key

VEORPZCZECFIRK-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
2-bromophenol
2-halophenol
Phenol
Halobenzene
Bromobenzene
Aryl halide
Aryl bromide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

bromobisphenol (CHEBI:33217 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	6.57	ALOGPS
logP	7.12	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.77 m³·mol⁻¹	ChemAxon
Polarizability	38.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6366

KEGG Compound ID

C13620

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrabromobisphenol_A

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

33217

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Ogunbayo OA, Michelangeli F: The widely utilized brominated flame retardant tetrabromobisphenol A (TBBPA) is a potent inhibitor of the SERCA Ca2+ pump. Biochem J. 2007 Dec 15;408(3):407-15. doi: 10.1042/BJ20070843. [PubMed:17784851 ]
Kim UJ, Oh JE: Tetrabromobisphenol A and hexabromocyclododecane flame retardants in infant-mother paired serum samples, and their relationships with thyroid hormones and environmental factors. Environ Pollut. 2014 Jan;184:193-200. doi: 10.1016/j.envpol.2013.08.034. Epub 2013 Sep 21. [PubMed:24060738 ]
Zhou X, Guo J, Zhang W, Zhou P, Deng J, Lin K: Tetrabromobisphenol A contamination and emission in printed circuit board production and implications for human exposure. J Hazard Mater. 2014 May 30;273:27-35. doi: 10.1016/j.jhazmat.2014.03.003. Epub 2014 Mar 16. [PubMed:24709479 ]
Vojdani A, Kharrazian D, Mukherjee PS: Elevated levels of antibodies against xenobiotics in a subgroup of healthy subjects. J Appl Toxicol. 2015 Apr;35(4):383-97. doi: 10.1002/jat.3031. Epub 2014 Jul 18. [PubMed:25042713 ]

Showing NP-Card for Tetrabromobisphenol A (NP0002796)

MOL for NP0002796 (Tetrabromobisphenol A)

3D MOL for NP0002796 (Tetrabromobisphenol A)

3D SDF for NP0002796 (Tetrabromobisphenol A)

3D-SDF for NP0002796 (Tetrabromobisphenol A)

PDB for NP0002796 (Tetrabromobisphenol A)

3D PDB for NP0002796 (Tetrabromobisphenol A)

SMILES for NP0002796 (Tetrabromobisphenol A)

INCHI for NP0002796 (Tetrabromobisphenol A)

Structure for NP0002796 (Tetrabromobisphenol A)

3D Structure for NP0002796 (Tetrabromobisphenol A)