NP-MRD: Showing NP-Card for WB2838 (NP0022797)

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Record Information

Version

2.0

Created at

2021-01-06 07:57:54 UTC

Updated at

2021-07-15 17:40:00 UTC

NP-MRD ID

NP0022797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

WB2838

Provided By

NPAtlas

Description

Aminopyrrolnitrin is also known as WB 2838. Aminopyrrolnitrin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. WB2838 is found in Burkholderia cepacia and Pseudomonas. It was first documented in 1993 (PMID: 8226310). Based on a literature review a small amount of articles have been published on aminopyrrolnitrin (PMID: 16150698) (PMID: 21507634) (PMID: 20865257) (PMID: 20373823) (PMID: 19884772) (PMID: 17921302).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105373D          

 22 23  0  0  0  0            999 V2000
   -1.0523   -1.8198    0.0964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2868   -0.4418   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817    0.0394   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854   -1.1102    0.1146 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    1.3911   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    2.2657   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5126    1.7865   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2318    0.4238   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1116   -0.0977   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -0.4007   -1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1540   -0.8586   -0.6248 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0466   -0.8416    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8052   -0.3804    1.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.1695    2.7110 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -2.2194    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629   -2.4976   -0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115    1.7336   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0148    3.3219   -0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    2.4724   -0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7392   -0.2959   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9942   -1.1665   -1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7876   -1.1346    1.4561 H   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8  2  1  0  0  0  0
 13  9  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  5 17  1  0  0  0  0
  6 18  1  0  0  0  0
  7 19  1  0  0  0  0
 10 20  1  0  0  0  0
 11 21  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C1=C(Cl)C([H])=C([H])C([H])=C1C1=C([H])N([H])C([H])=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C10H8Cl2N2/c11-8-3-1-2-6(10(8)13)7-4-14-5-9(7)12/h1-5,14H,13H2

> <INCHI_KEY>
RWAXAHFFXZKMPA-UHFFFAOYSA-N

> <FORMULA>
C10H8Cl2N2

> <MOLECULAR_WEIGHT>
227.09

> <EXACT_MASS>
226.0064537

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
21.935382330581454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-chloro-6-(4-chloro-1H-pyrrol-3-yl)aniline

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.079518689333333

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.35428892225527

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.06606596889617

> <JCHEM_PKA_STRONGEST_BASIC>
1.9909769447785055

> <JCHEM_POLAR_SURFACE_AREA>
41.81

> <JCHEM_REFRACTIVITY>
60.263000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-chloro-6-(4-chloro-1H-pyrrol-3-yl)aniline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -1.052  -1.820   0.096  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.287  -0.442  -0.011  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.582   0.039  -0.014  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -3.885  -1.110   0.115  0.00  0.00          Cl+0
HETATM    5  C   UNK     0      -2.880   1.391  -0.115  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.818   2.266  -0.216  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.513   1.787  -0.215  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.232   0.424  -0.111  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.112  -0.098  -0.097  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.964  -0.401  -1.105  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.154  -0.859  -0.625  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.047  -0.842   0.725  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.805  -0.380   1.088  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       1.161  -0.170   2.711  0.00  0.00          Cl+0
HETATM   15  H   UNK     0      -0.845  -2.219   1.042  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.063  -2.498  -0.691  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.912   1.734  -0.116  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.015   3.322  -0.297  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.320   2.472  -0.300  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.739  -0.296  -2.162  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.994  -1.167  -1.158  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.788  -1.135   1.456  0.00  0.00           H+0
CONECT    1    2   15   16                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14    9                                                  
CONECT   14   13                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-Chloro-4-(2-amino-3-chlorophenyl)pyrrole	ChEBI
WB 2838	ChEBI
WB-2838	ChEBI

Chemical Formula

C₁₀H₈Cl₂N₂

Average Mass

227.0900 Da

Monoisotopic Mass

226.00645 Da

IUPAC Name

2-chloro-6-(4-chloro-1H-pyrrol-3-yl)aniline

Traditional Name

2-chloro-6-(4-chloro-1H-pyrrol-3-yl)aniline

CAS Registry Number

Not Available

SMILES

NC1=C(C=CC=C1Cl)C1=CNC=C1Cl

InChI Identifier

InChI=1S/C10H8Cl2N2/c11-8-3-1-2-6(10(8)13)7-4-14-5-9(7)12/h1-5,14H,13H2

InChI Key

RWAXAHFFXZKMPA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Burkholderia cepacia	LOTUS Database	35616633
Pseudomonas	NPAtlas	8226310

Chemical Taxonomy

Description

This compound 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

3-phenylpyrrole
Aniline or substituted anilines
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

substituted aniline (CHEBI:85786 )
indole alkaloid (CHEBI:85786 )
monochlorobenzenes (CHEBI:85786 )
ring assembly (CHEBI:85786 )
pyrroles (CHEBI:85786 )
a chloroaromatic compound (CPD-12775 )

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	3.56	ALOGPS
logP	3.08	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	16.07	ChemAxon
pKa (Strongest Basic)	1.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.81 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.26 m³·mol⁻¹	ChemAxon
Polarizability	21.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA012857

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

141586

KEGG Compound ID

Not Available

BioCyc ID

CPD-12775

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161174

PDB ID

Not Available

ChEBI ID

85786

Good Scents ID

Not Available

References

General References

Hori Y, Abe Y, Nakajima H, Takase S, Fujita T, Goto T, Okuhara M, Kohsaka M: WB2838 [3-chloro-4-(2-amino-3-chlorophenyl)-pyrrole]: non-steroidal androgen-receptor antagonist produced by a Pseudomonas. J Antibiot (Tokyo). 1993 Sep;46(9):1327-33. doi: 10.7164/antibiotics.46.1327. [PubMed:8226310 ]
Lee J, Simurdiak M, Zhao H: Reconstitution and characterization of aminopyrrolnitrin oxygenase, a Rieske N-oxygenase that catalyzes unusual arylamine oxidation. J Biol Chem. 2005 Nov 4;280(44):36719-27. doi: 10.1074/jbc.M505334200. Epub 2005 Sep 2. [PubMed:16150698 ]
Tiwari MK, Lee JK, Moon HJ, Zhao H: Further biochemical studies on aminopyrrolnitrin oxygenase (PrnD). Bioorg Med Chem Lett. 2011 May 15;21(10):2873-6. doi: 10.1016/j.bmcl.2011.03.087. Epub 2011 Mar 30. [PubMed:21507634 ]
Keum YS, Zhu YZ, Kim JH: Structure-inhibitory activity relationships of pyrrolnitrin analogues on its biosynthesis. Appl Microbiol Biotechnol. 2011 Feb;89(3):781-9. doi: 10.1007/s00253-010-2872-0. Epub 2010 Sep 24. [PubMed:20865257 ]
Keum YS, Lee HR, Kim JH: Effects of pesticides on the bacterial production of pyrrolnitrin. J Agric Food Chem. 2010 May 12;58(9):5531-7. doi: 10.1021/jf904195j. [PubMed:20373823 ]
Keum YS, Lee YJ, Lee YH, Kim JH: Effects of nutrients on quorum signals and secondary metabolite productions of Burkholderia sp. O33. J Microbiol Biotechnol. 2009 Oct;19(10):1142-9. doi: 10.4014/jmb.0901.465. [PubMed:19884772 ]
Lee JK, Zhao H: Identification and characterization of the flavin:NADH reductase (PrnF) involved in a novel two-component arylamine oxygenase. J Bacteriol. 2007 Dec;189(23):8556-63. doi: 10.1128/JB.01050-07. Epub 2007 Oct 5. [PubMed:17921302 ]
Lee JK, Ang EL, Zhao H: Probing the substrate specificity of aminopyrrolnitrin oxygenase (PrnD) by mutational analysis. J Bacteriol. 2006 Sep;188(17):6179-83. doi: 10.1128/JB.00259-06. [PubMed:16923884 ]
Lee J, Zhao H: Mechanistic studies on the conversion of arylamines into arylnitro compounds by aminopyrrolnitrin oxygenase: identification of intermediates and kinetic studies. Angew Chem Int Ed Engl. 2006 Jan 16;45(4):622-5. doi: 10.1002/anie.200502903. [PubMed:16342311 ]

Showing NP-Card for WB2838 (NP0022797)

MOL for NP0022797 (WB2838)

3D MOL for NP0022797 (WB2838)

3D SDF for NP0022797 (WB2838)

3D-SDF for NP0022797 (WB2838)

PDB for NP0022797 (WB2838)

3D PDB for NP0022797 (WB2838)

SMILES for NP0022797 (WB2838)

INCHI for NP0022797 (WB2838)

Structure for NP0022797 (WB2838)

3D Structure for NP0022797 (WB2838)