NP-MRD: Showing NP-Card for 1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene (NP0333996)

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Record Information

Version

2.0

Created at

2024-09-09 21:35:53 UTC

Updated at

2024-09-09 21:35:53 UTC

NP-MRD ID

NP0333996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene

Description

Classified as a Food Contaminant (code WG) in the DFC

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 09051417072D          

 18 19  0  0  0  0            999 V2000
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    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
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  2  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 12 10  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=CC(Br)=C(OC2=C(Br)C=C(Br)C(Br)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H5Br5O/c13-6-1-2-11(9(16)3-6)18-12-5-8(15)7(14)4-10(12)17/h1-5H

> <INCHI_KEY>
WHPVYXDFIXRKLN-UHFFFAOYSA-N

> <FORMULA>
C12H5Br5O

> <MOLECULAR_WEIGHT>
564.688

> <EXACT_MASS>
559.625728017

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
35.273941653334816

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,4-tribromo-5-(2,4-dibromophenoxy)benzene

> <ALOGPS_LOGP>
6.69

> <JCHEM_LOGP>
7.317296125666666

> <ALOGPS_LOGS>
-6.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7506350336284506

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
90.41280000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentabromodiphenyl ether

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0      -1.334   2.310   0.000  0.00  0.00          Br+0
HETATM   14 Br   UNK     0       4.001  11.550   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0       1.334  13.090   0.000  0.00  0.00          Br+0
HETATM   16 Br   UNK     0      -4.001   6.930   0.000  0.00  0.00          Br+0
HETATM   17 Br   UNK     0       1.334   6.930   0.000  0.00  0.00          Br+0
HETATM   18  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1   11                                                       
CONECT    3    6    9                                                       
CONECT    4    7   10                                                       
CONECT    5    8   12                                                       
CONECT    6    1    3   13                                                  
CONECT    7    4    8   14                                                  
CONECT    8    5    7   15                                                  
CONECT    9    3   11   16                                                  
CONECT   10    4   12   17                                                  
CONECT   11    2    9   18                                                  
CONECT   12    5   10   18                                                  
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene	ChEBI
2,2',4,4',5-Pentabromodiphenyl ether	ChEBI
BDE 99	ChEBI
BDE-99	ChEBI
PBDE 99	ChEBI
PBDE-99	ChEBI
2,2',3,4,4'-Pentabromodiphenyl ether	HMDB
2,2',4,4',6-Pentabromodiphenyl ether	HMDB
DE-71	HMDB
PBDE 85	HMDB
DE 71	HMDB
2,2',4,4',5-PentaBDE	HMDB
PBDE	HMDB
PBDE 100	HMDB
Pentabromodiphenyl ether	HMDB
Pentabromodiphenyl ether (mixed isomers)	MeSH

Chemical Formula

C₁₂H₅Br₅O

Average Mass

564.6880 Da

Monoisotopic Mass

559.62573 Da

IUPAC Name

1,2,4-tribromo-5-(2,4-dibromophenoxy)benzene

Traditional Name

pentabromodiphenyl ether

CAS Registry Number

Not Available

SMILES

BrC1=CC(Br)=C(OC2=C(Br)C=C(Br)C(Br)=C2)C=C1

InChI Identifier

InChI=1S/C12H5Br5O/c13-6-1-2-11(9(16)3-6)18-12-5-8(15)7(14)4-10(12)17/h1-5H

InChI Key

WHPVYXDFIXRKLN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bromodiphenyl ethers. Bromodiphenyl ethers are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Bromodiphenyl ethers

Alternative Parents

Substituents

Bromodiphenyl ether
Diaryl ether
Phenoxy compound
Phenol ether
Halobenzene
Bromobenzene
Aryl halide
Aryl bromide
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:81582 )
aromatic ether (CHEBI:81582 )
PBDEs (C18203 )

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	6.69	ALOGPS
logP	7.32	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.41 m³·mol⁻¹	ChemAxon
Polarizability	35.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037516

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016613

KNApSAcK ID

Not Available

Chemspider ID

33255

KEGG Compound ID

C18203

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

36159

PDB ID

Not Available

ChEBI ID

81582

Good Scents ID

Not Available

References

General References

Winter V, Williams TD, Elliott JE: A three-generational study of In ovo exposure to PBDE-99 in the zebra finch. Environ Toxicol Chem. 2013 Mar;32(3):562-8. doi: 10.1002/etc.2102. [PubMed:23258742 ]
Eng ML, Elliott JE, Williams TD: An assessment of the developmental toxicity of BDE-99 in the European starling using an integrated laboratory and field approach. Ecotoxicology. 2014 Oct;23(8):1505-16. doi: 10.1007/s10646-014-1292-9. Epub 2014 Aug 1. [PubMed:25081382 ]
Erratico C, Currier H, Szeitz A, Bandiera S, Covaci A, Elliott J: Levels of PBDEs in plasma of juvenile starlings (Sturnus vulgaris) from British Columbia, Canada and assessment of PBDE metabolism by avian liver microsomes. Sci Total Environ. 2015 Jun 15;518-519:31-7. doi: 10.1016/j.scitotenv.2014.12.102. Epub 2015 Mar 3. [PubMed:25747361 ]
Wang F, Ruan XJ, Zhang HY: BDE-99 (2,2',4,4',5-pentabromodiphenyl ether) triggers epithelial-mesenchymal transition in colorectal cancer cells via PI3K/Akt/Snail signaling pathway. Tumori. 2015 Mar-Apr;101(2):238-45. doi: 10.5301/tj.5000229. Epub 2015 Apr 9. [PubMed:25908029 ]
Erratico C, Zheng X, Ryden A, Marsh G, Maho W, Covaci A: Human hydroxylated metabolites of BDE-47 and BDE-99 are glucuronidated and sulfated in vitro. Toxicol Lett. 2015 Jul 16;236(2):98-109. doi: 10.1016/j.toxlet.2015.05.003. Epub 2015 May 5. [PubMed:25956475 ]

Showing NP-Card for 1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene (NP0333996)

MOL for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

3D MOL for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

3D SDF for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

3D-SDF for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

PDB for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

3D PDB for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

SMILES for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

INCHI for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

Structure for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)

3D Structure for NP0333996 (1,2,4-Tribromo-5-(2,4-dibromophenoxy)benzene)