Np mrd loader

Showing NP-Card for 2-Bromophenol (NP0074936)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-28 20:14:07 UTC
Updated at2022-04-28 20:14:08 UTC
NP-MRD IDNP0074936
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Bromophenol
Description2-Bromophenol belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring. 2-Bromophenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Monobromrophenols have three isomers because there is only one bromine atom that can occupy one of three ring positions on the phenol molecule; 2-bromophenol, for example, is the isomer that has a bromine atom in the ortho position. There are five basic types of bromophenols (mono- to pentabromophenol) and 19 different bromophenols in total when positional isomerism is taken into account. Bromophenols are produced by electrophilic halogenation of phenol with bromine. Pentabromophenol, by contrast, has only one isomer because all five available ring positions on the phenol are fully chlorinated. A bromophenol is any organobromide of phenol that contains one or more covalently bonded bromine atoms. 2-Bromophenol is found in Polysiphonia sphaerocarpa and Ulva lactuca. 2-Bromophenol was first documented in 2009 (PMID: 19488620). There is a total of 19 bromophenols, corresponding to the different ways in which bromine atoms can be attached to the five carbon atoms in the benzene ring of the phenol molecule, excluding the carbon atom to which the hydroxy group is attached (PMID: 23369690) (PMID: 23325557) (PMID: 23377268) (PMID: 23364683).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0074936 (2-Bromophenol)


  Mrv0541 02231217472D          

  8  8  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 O   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    0.0000    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
    0.0000    0.0000    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0074936 (2-Bromophenol)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    2.4486   -0.1468   -0.3909 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -0.1014   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -1.2684   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385   -1.2825   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -0.1124    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9400    1.0379    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247    1.0656    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3979    2.6891    0.3025 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0220    0.6840   -0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.1910   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -2.1782   -0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7669   -0.1393    0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4894    1.9437    0.5894 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
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
M  END
Download

3D SDF for NP0074936 (2-Bromophenol)


  Mrv0541 02231217472D          

  8  8  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 O   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    0.0000    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
    0.0000    0.0000    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC=C1Br

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

> <INCHI_KEY>
VADKRMSMGWJZCF-UHFFFAOYSA-N

> <FORMULA>
C6H5BrO

> <MOLECULAR_WEIGHT>
173.007

> <EXACT_MASS>
171.952377429

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.05140895799505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-bromophenol

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.438433119666666

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.155259313633366

> <JCHEM_PKA_STRONGEST_BASIC>
-6.676418492388259

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
35.661699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bromophenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0074936 (2-Bromophenol)

Download
PDB for NP0074936 (2-Bromophenol)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8 Br   UNK     0       1.334   3.850   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

Download
3D PDB for NP0074936 (2-Bromophenol)
Download
SMILES for NP0074936 (2-Bromophenol)
OC1=CC=CC=C1Br
Download
INCHI for NP0074936 (2-Bromophenol)
InChI=1S/C6H5BrO/c7-5-3-1-2-4-6(5)8/h1-4,8H
Download
View in JSmol
Synonyms
ValueSource
O-BromophenolKegg
2-BromfenolHMDB
2-Bromo-phenolHMDB
Bromo-phenolHMDB
BromophenolHMDB
O-Bromo-phenolHMDB
Ortho-bromophenolHMDB
Chemical FormulaC6H5BrO
Average Mass173.0070 Da
Monoisotopic Mass171.95238 Da
IUPAC Name2-bromophenol
Traditional Namebromophenol
CAS Registry NumberNot Available
SMILES
OC1=CC=CC=C1Br
InChI Identifier
InChI=1S/C6H5BrO/c7-5-3-1-2-4-6(5)8/h1-4,8H
InChI KeyVADKRMSMGWJZCF-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
Polysiphonia sphaerocarpa--
Ulva lactucaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassHalophenols  
Direct ParentO-bromophenols  
Alternative Parents
Substituents
  • 2-bromophenol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 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
logP2.52ALOGPS
logP2.44ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.16ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.66 m³·mol⁻¹ChemAxon
Polarizability13.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032059  
DrugBank IDDB04586  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008766  
KNApSAcK IDC00036481  
Chemspider ID6974  
KEGG Compound IDC14841  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBromophenol  
METLIN IDNot Available
PubChem Compound7244  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Oliveira AS, Silva VM, Veloso MC, Santos GV, Andrade JB: Bromophenol concentrations in fish from Salvador, BA, Brazil. An Acad Bras Cienc. 2009 Jun;81(2):165-72. [PubMed:19488620  ] 
  2. Forootanfar H, Moezzi A, Aghaie-Khozani M, Mahmoudjanlou Y, Ameri A, Niknejad F, Faramarzi MA: Synthetic dye decolorization by three sources of fungal laccase. Iranian J Environ Health Sci Eng. 2012 Dec 15;9(1):27. doi:  10.1186/1735-2746-9-27. [PubMed:23369690  ] 
  3. de Serrano V, Franzen S: Structural evidence for stabilization of inhibitor binding by a protein cavity in the dehaloperoxidase-hemoglobin from Amphitrite ornata. Biopolymers. 2012;98(1):27-35. doi: 10.1002/bip.21674. Epub 2011 May 17. [PubMed:23325557  ] 
  4. Martinez NS, Machado JM, Perez-Saad H, Coro-Antich RM, Berlanga-Acosta JA, Salgueiro SR, Illera GG, Alba JS, del Barco DG: Global brain ischemia in Mongolian gerbils: assessing the level of anastomosis in the cerebral circle of Willis. Acta Neurobiol Exp (Wars). 2012;72(4):377-84. [PubMed:23377268  ] 
  5. Shi D, Guo S, Jiang B, Guo C, Wang T, Zhang L, Li J: HPN, a synthetic analogue of bromophenol from red alga Rhodomela confervoides: synthesis and anti-diabetic effects in C57BL/KsJ-db/db mice. Mar Drugs. 2013 Jan 30;11(2):350-62. doi: 10.3390/md11020350. [PubMed:23364683  ]