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Showing NP-Card for 4-Bromophenol (NP0074995)

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Record Information
Version2.0
Created at2022-04-28 20:18:47 UTC
Updated at2022-04-28 20:18:47 UTC
NP-MRD IDNP0074995
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Bromophenol
Description4-Bromophenol belongs to the class of organic compounds known as p-bromophenols. These are bromophenols carrying a iodine at the C4 position of the benzene ring. 4-Bromophenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Bromophenol is found in Mus musculus, Polysiphonia sphaerocarpa and Ulva lactuca. 4-Bromophenol was first documented in 2001 (PMID: 11434383). A bromophenol containing only hydroxy and bromo substituents that are para to one another (PMID: 12584764) (PMID: 17622410) (PMID: 21045326) (PMID: 22827705).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0074995 (4-Bromophenol)


  Mrv0541 05041400592D          

  8  8  0  0  0  0            999 V2000
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for NP0074995 (4-Bromophenol)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    1.9617   -0.2356    1.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295   -0.0933    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -1.1681   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5102   -1.0335   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1474    0.1742   -1.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    0.3447   -2.4142 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225    1.2502   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    1.1148    0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6609   -0.4929    2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0113   -2.1218    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211   -1.9019   -1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2322    2.1887   -0.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225    1.9746    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
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3D SDF for NP0074995 (4-Bromophenol)


  Mrv0541 05041400592D          

  8  8  0  0  0  0            999 V2000
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(Br)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5BrO/c7-5-1-3-6(8)4-2-5/h1-4,8H

> <INCHI_KEY>
GZFGOTFRPZRKDS-UHFFFAOYSA-N

> <FORMULA>
C6H5BrO

> <MOLECULAR_WEIGHT>
173.007

> <EXACT_MASS>
171.952377429

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.187888441435987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-bromophenol

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.438433119666666

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.091221423883503

> <JCHEM_PKA_STRONGEST_BASIC>
-6.263650230613627

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
35.661699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-bromophenol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0074995 (4-Bromophenol)

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PDB for NP0074995 (4-Bromophenol)
HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    5                                                       
CONECT    3    1    6                                                       
CONECT    4    2    6                                                       
CONECT    5    1    2    7                                                  
CONECT    6    3    4    8                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0074995 (4-Bromophenol)
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SMILES for NP0074995 (4-Bromophenol)
OC1=CC=C(Br)C=C1
Download
INCHI for NP0074995 (4-Bromophenol)
InChI=1S/C6H5BrO/c7-5-1-3-6(8)4-2-5/h1-4,8H
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View in JSmol
Synonyms
ValueSource
p-BromohydroxybenzeneChEBI
p-BromophenolChEBI
4-Bromo-phenolHMDB
Para-bromophenolHMDB
Chemical FormulaC6H5BrO
Average Mass173.0070 Da
Monoisotopic Mass171.95238 Da
IUPAC Name4-bromophenol
Traditional Name4-bromophenol
CAS Registry NumberNot Available
SMILES
OC1=CC=C(Br)C=C1
InChI Identifier
InChI=1S/C6H5BrO/c7-5-1-3-6(8)4-2-5/h1-4,8H
InChI KeyGZFGOTFRPZRKDS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mus musculusLOTUS Database
Polysiphonia sphaerocarpa--
Ulva lactucaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-bromophenols. These are bromophenols carrying a iodine at the C4 position of the benzene ring.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassHalophenols  
Direct ParentP-bromophenols  
Alternative Parents
Substituents
  • 4-bromophenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Halobenzene
    • 

  • Bromobenzene
    • 

  • Monocyclic benzene moiety
    • 

  • Aryl halide
    • 

  • Aryl bromide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organobromide
    • 

  • Organohalogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.5ALOGPS
logP2.44ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.66 m³·mol⁻¹ChemAxon
Polarizability13.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062397  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00036569  
Chemspider IDNot Available
KEGG Compound IDC14453  
BioCyc IDCPD-18749  
BiGG IDNot Available
Wikipedia LinkBromophenol  
METLIN IDNot Available
PubChem Compound7808  
PDB IDNot Available
ChEBI ID47248  
Good Scents IDNot Available
References
General References
  1. Kamitori S, Toyama Y, Matsuzaka O: Crystal structures of cyclomaltohexaose (alpha-cyclodextrin) complexes with p-bromophenol and m-bromophenol. Carbohydr Res. 2001 May 18;332(2):235-40. doi: 10.1016/s0008-6215(01)00086-6. [PubMed:11434383  ] 
  2. Levy I, Ward G, Hadar Y, Shoseyov O, Dosoretz CG: Oxidation of 4-bromophenol by the recombinant fused protein cellulose-binding domain-horseradish peroxidase immobilized on cellulose. Biotechnol Bioeng. 2003 Apr 20;82(2):223-31. doi: 10.1002/bit.10562. [PubMed:12584764  ] 
  3. Devine AL, Nix MG, Cronin B, Ashfold MN: Near-UV photolysis of substituted phenols, I: 4-fluoro-, 4-chloro- and 4-bromophenol. Phys Chem Chem Phys. 2007 Jul 28;9(28):3749-62. doi: 10.1039/b704146b. Epub 2007  May 29. [PubMed:17622410  ] 
  4. Meizler A, Roddick FA, Porter NA: Continuous enzymatic treatment of 4-bromophenol initiated by UV irradiation. Water Sci Technol. 2010;62(9):2016-20. doi: 10.2166/wst.2010.550. [PubMed:21045326  ] 
  5. Koen YM, Hajovsky H, Liu K, Williams TD, Galeva NA, Staudinger JL, Hanzlik RP: Liver protein targets of hepatotoxic 4-bromophenol metabolites. Chem Res Toxicol. 2012 Aug 20;25(8):1777-86. doi: 10.1021/tx3002675. Epub 2012 Aug 3. [PubMed:22827705  ]