NP-MRD: Showing NP-Card for pentabromopseudilin (NP0295832)

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Record Information

Version

2.0

Created at

2022-09-10 05:02:56 UTC

Updated at

2022-09-10 05:02:56 UTC

NP-MRD ID

NP0295832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pentabromopseudilin

Description

Pentabromopseudilin belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond. Pentabromopseudilin, the first reported marine microbial antibiotic, is a bioactive natural product that contains a highly halogenated 2-arrylpyrrole moiety. It was found that the incorporation of a variety of glucose labels ([2-13C]-, [1,2-13C2]-, and [3-13C]), indicated that the PBP benzene ring is derived from carbohydrate metabolism and have occurred through erythrose 4-phosphate. From these results indicating a shikimic acid derivation, it was further deduced that p-hydroxybenzoic acid (4-HBA) be a plausible precursor for PBP's phenol group. Pentabromopseudilin is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-HBA is then di-halogenated by the flavin-dependent halogenase, Bmp5 (Hal), to yield 2,3-dibromophenol. Early investigations from this first report pointed at intrigue in regards to the pyrrole's particularly potent activity against gram positive bacteria, namely the strains Staphylococcus aureus, Diplococcus pneumoniae and Streptococcus pyogenes. The biosynthesis of PBP was first shown through isotope feeding studies, and then biochemically when genomic data of PBP-producing strains became readily available.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041409222D          

 17 18  0  0  0  0            999 V2000
   -0.7604   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -0.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8806   -0.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -1.8216    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7011   -0.1418    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    2.0602    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    1.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0295832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(C=C(Br)C=C1Br)C1=C(Br)C(Br)=C(Br)N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H4Br5NO/c11-3-1-4(9(17)5(12)2-3)8-6(13)7(14)10(15)16-8/h1-2,16-17H

> <INCHI_KEY>
LXMNWKJHYOZUQL-UHFFFAOYSA-N

> <FORMULA>
C10H4Br5NO

> <MOLECULAR_WEIGHT>
553.665

> <EXACT_MASS>
548.62097699

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
34.15271469748652

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol

> <ALOGPS_LOGP>
5.92

> <JCHEM_LOGP>
5.860909712333333

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.757523265987363

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.246500428015781

> <JCHEM_PKA_STRONGEST_BASIC>
-7.135491171206495

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
85.7074

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.12e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol

> <JCHEM_VEBER_RULE>
1

$$$$

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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM   12 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM   13 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM   14 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2   11                                                  
CONECT    4    1    8    9                                                  
CONECT    5    2    9   12                                                  
CONECT    6    7    8   13                                                  
CONECT    7    6   10   14                                                  
CONECT    8    4    6   16                                                  
CONECT    9    4    5   17                                                  
CONECT   10    7   15   16                                                  
CONECT   11    3                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15   10                                                            
CONECT   16    8   10                                                       
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
2,3,4-Tribromo-5-(3,5-dibromo-2-hydroxyphenyl)-1H-pyrrole	MeSH

Chemical Formula

C₁₀H₄Br₅NO

Average Mass

553.6650 Da

Monoisotopic Mass

548.62098 Da

IUPAC Name

2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol

Traditional Name

2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol

CAS Registry Number

Not Available

SMILES

OC1=C(C=C(Br)C=C1Br)C1=C(Br)C(Br)=C(Br)N1

InChI Identifier

InChI=1S/C10H4Br5NO/c11-3-1-4(9(17)5(12)2-3)8-6(13)7(14)10(15)16-8/h1-2,16-17H

InChI Key

LXMNWKJHYOZUQL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Substituents

2-phenylpyrrole
4-halophenol
2-halophenol
2-bromophenol
4-bromophenol
Bromobenzene
Halobenzene
Phenol
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Azacycle
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrroles (CHEBI:70619 )

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	5.92	ALOGPS
logP	5.86	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	7.25	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.71 m³·mol⁻¹	ChemAxon
Polarizability	34.15 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pentabromopseudilin

METLIN ID

Not Available

PubChem Compound

324093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for pentabromopseudilin (NP0295832)

MOL for NP0295832 (pentabromopseudilin)

3D MOL for NP0295832 (pentabromopseudilin)

3D SDF for NP0295832 (pentabromopseudilin)

3D-SDF for NP0295832 (pentabromopseudilin)

PDB for NP0295832 (pentabromopseudilin)

3D PDB for NP0295832 (pentabromopseudilin)

SMILES for NP0295832 (pentabromopseudilin)

INCHI for NP0295832 (pentabromopseudilin)

Structure for NP0295832 (pentabromopseudilin)

3D Structure for NP0295832 (pentabromopseudilin)