NP-MRD: Showing NP-Card for NSC 107654 (NP0062267)

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Record Information

Version

2.0

Created at

2022-04-28 06:56:56 UTC

Updated at

2022-04-28 06:56:56 UTC

NP-MRD ID

NP0062267

Secondary Accession Numbers

None

Natural Product Identification

Common Name

NSC 107654

Description

Pyrrolnitrin, also known as NSC 107654, 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. The fungicides fenpiclonil and fludioxonil are chemically related to pyrrolnitrin. Pyrrolnitrin is an extremely weak acidic (essentially neutral) compound (based on its pKa). Pseudomonas pyrrocinia and other Pseudomonas species produce pyrrolnitrin from tryptophan as secondary metabolite. NSC 107654 is found in Acinetobacter haemolyticus, Burkholderia cepacia, Burkholderia pyrrocinia, Pantoea agglomerans, Pseudomonas chlororaphis, Pseudomonas pyrrocinia No. 2327 and Streptomyces phaeochromogenes. NSC 107654 was first documented in 1965 (PMID: 4379208). Pyrrolnitrin is an antifungal antibiotic (PMID: 23149469) (PMID: 23990066) (PMID: 25679537) (PMID: 25901993).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241514382D          

 16 17  0  0  0  0            999 V2000
    1.3222   -0.0616    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    2.4134    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032   -0.2916    0.0000 Cl  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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0062267

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H

> <INCHI_KEY>
QJBZDBLBQWFTPZ-UHFFFAOYSA-N

> <FORMULA>
C10H6Cl2N2O2

> <MOLECULAR_WEIGHT>
257.07

> <EXACT_MASS>
255.9806328

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
22.535194748895407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
3.848428832666667

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.061515816511207

> <JCHEM_POLAR_SURFACE_AREA>
58.93

> <JCHEM_REFRACTIVITY>
61.883100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrrolnitrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       2.468  -0.115   0.000  0.00  0.00           O-1
HETATM    2  N   UNK     0       2.468   1.425   0.000  0.00  0.00           N+1
HETATM    3  O   UNK     0       1.134   2.195   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       2.468   4.505   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.469   3.735   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.890  -1.020   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.366  -2.485   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       7.846  -0.544   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
3-Chloro-4-(2'-nitro-3'-chlorophenyl)pyrrole	ChEBI
3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole	ChEBI
NSC 107654	ChEBI
NSC-107654	ChEBI
Pirrolnitrina	ChEBI
Pyrrolnitrine	ChEBI
Pyrrolnitrinum	ChEBI

Chemical Formula

C₁₀H₆Cl₂N₂O₂

Average Mass

257.0700 Da

Monoisotopic Mass

255.98063 Da

IUPAC Name

3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole

Traditional Name

pyrrolnitrin

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl

InChI Identifier

InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H

InChI Key

QJBZDBLBQWFTPZ-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
Acinetobacter haemolyticus	LOTUS Database	35616633
Burkholderia cepacia	LOTUS Database	35616633
Burkholderia pyrrocinia	LOTUS Database	35616633
Pantoea agglomerans	LOTUS Database	35616633
Pseudomonas chlororaphis	LOTUS Database	35616633
Pseudomonas pyrrocinia No. 2327	Bacteria	KNApSAcK
Streptomyces phaeochromogenes	LOTUS Database	35616633

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

3-phenylpyrrole
Nitrobenzene
Nitroaromatic compound
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Organic nitro compound
C-nitro compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Azacycle
Organic oxoazanium
Organic 1,3-dipolar compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:32079 )
indole alkaloid (CHEBI:32079 )
monochlorobenzenes (CHEBI:32079 )
ring assembly (CHEBI:32079 )
pyrroles (CHEBI:32079 )
a chloroaromatic compound (CPD-12776 )

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	3.86	ALOGPS
logP	3.85	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	15.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.88 m³·mol⁻¹	ChemAxon
Polarizability	22.54 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

HMDB ID

Not Available

DrugBank ID

DB13603

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018726

Chemspider ID

Not Available

KEGG Compound ID

C12491

BioCyc ID

CPD-12776

BiGG ID

Not Available

Wikipedia Link

Pyrrolnitrin

METLIN ID

Not Available

PubChem Compound

13916

PDB ID

Not Available

ChEBI ID

32079

Good Scents ID

Not Available

References

General References

Thongsri Y, Aromdee C, Yenjai C, Kanokmedhakul S, Chaiprasert A, Hamal P, Prariyachatigul C: Detection of diketopiperazine and pyrrolnitrin, compounds with anti-Pythium insidiosum activity, in a Pseudomonas stutzeri environmental strain. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2014 Sep;158(3):378-83. doi: 10.5507/bp.2012.090. Epub 2012 Nov 13. [PubMed:23149469 ]
Mujumdar SS, Bashetti SP, Chopade BA: Plasmid pUPI126-encoded pyrrolnitrin production by Acinetobacter haemolyticus A19 isolated from the rhizosphere of wheat. World J Microbiol Biotechnol. 2014 Feb;30(2):495-505. doi: 10.1007/s11274-013-1426-x. Epub 2013 Aug 30. [PubMed:23990066 ]
Calderon CE, Ramos C, de Vicente A, Cazorla FM: Comparative Genomic Analysis of Pseudomonas chlororaphis PCL1606 Reveals New Insight into Antifungal Compounds Involved in Biocontrol. Mol Plant Microbe Interact. 2015 Mar;28(3):249-60. doi: 10.1094/MPMI-10-14-0326-FI. [PubMed:25679537 ]
Nandi M, Selin C, Brassinga AK, Belmonte MF, Fernando WG, Loewen PC, de Kievit TR: Pyrrolnitrin and Hydrogen Cyanide Production by Pseudomonas chlororaphis Strain PA23 Exhibits Nematicidal and Repellent Activity against Caenorhabditis elegans. PLoS One. 2015 Apr 22;10(4):e0123184. doi: 10.1371/journal.pone.0123184. eCollection 2015. [PubMed:25901993 ]
Nishida M, Matsubara T, Watanabe N: Pyrrolnitrin, a new antifungal antibiotic. Microbiological and toxicological observations. J Antibiot (Tokyo). 1965 Sep;18(5):211-9. [PubMed:4379208 ]

Showing NP-Card for NSC 107654 (NP0062267)

MOL for NP0062267 (NSC 107654)

3D MOL for NP0062267 (NSC 107654)

3D SDF for NP0062267 (NSC 107654)

3D-SDF for NP0062267 (NSC 107654)

PDB for NP0062267 (NSC 107654)

3D PDB for NP0062267 (NSC 107654)

SMILES for NP0062267 (NSC 107654)

INCHI for NP0062267 (NSC 107654)

Structure for NP0062267 (NSC 107654)

3D Structure for NP0062267 (NSC 107654)