Np mrd loader

Showing NP-Card for monodechloroaminopyrrolnitrin (NP0261950)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-08 04:32:39 UTC
Updated at2022-09-08 04:32:39 UTC
NP-MRD IDNP0261950
Secondary Accession NumbersNone
Natural Product Identification
Common Namemonodechloroaminopyrrolnitrin
DescriptionMonodechloroaminopyrrolnitrin, also known as 2-chloro-6-(pyrrol-3-yl)aniline or 4-(2-amino-3-chlorophenyl)pyrrole, 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. Monodechloroaminopyrrolnitrin 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. monodechloroaminopyrrolnitrin is found in Burkholderia cepacia. monodechloroaminopyrrolnitrin was first documented in 2003 (PMID: 14616084). Based on a literature review a small amount of articles have been published on monodechloroaminopyrrolnitrin (PMID: 17924666) (PMID: 15321684).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0261950 (monodechloroaminopyrrolnitrin)


  Mrv1652309082206322D          

 13 14  0  0  0  0            999 V2000
    1.3222    0.7634    0.0000 N   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
    3.4186   -0.5465    0.0000 C   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
    2.3387   -1.3312    0.0000 N   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
  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
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  2  0  0  0  0
M  END
Download

3D MOL for NP0261950 (monodechloroaminopyrrolnitrin)

     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -0.6807    1.9233   -0.5702 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2341    0.6918   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6066    0.5205   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980    1.8546   -0.4014 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278   -0.6890    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -1.7171    0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887   -1.5352    0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -0.3353    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -0.1373   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8633    0.9274    0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881    0.7186    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396   -0.4877   -0.5328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980   -1.0081   -0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945    2.0013   -1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432    2.7766    0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1897   -0.8283    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6402   -2.6729    0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867   -2.3482    0.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5014    1.8122    0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9992    1.3983    0.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1379   -0.9038   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602   -1.9616   -1.0510 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 13  2  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
  8  2  1  0
 10  9  1  0
  1 14  1  0
  1 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 13 22  1  0
 12 21  1  0
 11 20  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0261950 (monodechloroaminopyrrolnitrin)


  Mrv1652309082206322D          

 13 14  0  0  0  0            999 V2000
    1.3222    0.7634    0.0000 N   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
    3.4186   -0.5465    0.0000 C   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
    2.3387   -1.3312    0.0000 N   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
  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
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0261950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(Cl)C=CC=C1C1=CNC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H9ClN2/c11-9-3-1-2-8(10(9)12)7-4-5-13-6-7/h1-6,13H,12H2

> <INCHI_KEY>
VLWKKIHFPGKVHZ-UHFFFAOYSA-N

> <FORMULA>
C10H9ClN2

> <MOLECULAR_WEIGHT>
192.65

> <EXACT_MASS>
192.045426

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
19.666292838909264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.475474013

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.67757584758046

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.301129010678025

> <JCHEM_PKA_STRONGEST_BASIC>
2.436094832872043

> <JCHEM_POLAR_SURFACE_AREA>
41.81

> <JCHEM_REFRACTIVITY>
55.45820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0261950 (monodechloroaminopyrrolnitrin)

Download
PDB for NP0261950 (monodechloroaminopyrrolnitrin)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  N   UNK     0       2.468   1.425   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       2.468   4.505   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.469   3.735   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.366  -2.485   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.890  -1.020   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Download
3D PDB for NP0261950 (monodechloroaminopyrrolnitrin)
Download
SMILES for NP0261950 (monodechloroaminopyrrolnitrin)
NC1=C(Cl)C=CC=C1C1=CNC=C1
Download
INCHI for NP0261950 (monodechloroaminopyrrolnitrin)
InChI=1S/C10H9ClN2/c11-9-3-1-2-8(10(9)12)7-4-5-13-6-7/h1-6,13H,12H2
Download
View in JSmol
Synonyms
ValueSource
2-Chloro-6-(1H-pyrrol-3-yl)benzenamineChEBI
2-Chloro-6-(pyrrol-3-yl)anilineChEBI
4-(2-Amino-3-chlorophenyl)pyrroleChEBI
4-ACPPMeSH
Chemical FormulaC10H9ClN2
Average Mass192.6500 Da
Monoisotopic Mass192.04543 Da
IUPAC Name2-chloro-6-(1H-pyrrol-3-yl)aniline
Traditional Name2-chloro-6-(1H-pyrrol-3-yl)aniline
CAS Registry NumberNot Available
SMILES
NC1=C(Cl)C=CC=C1C1=CNC=C1
InChI Identifier
InChI=1S/C10H9ClN2/c11-9-3-1-2-8(10(9)12)7-4-5-13-6-7/h1-6,13H,12H2
InChI KeyVLWKKIHFPGKVHZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Burkholderia cepaciaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrroles  
Sub ClassSubstituted pyrroles  
Direct ParentPhenylpyrroles  
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP2.48ChemAxon
pKa (Strongest Acidic)17.3ChemAxon
pKa (Strongest Basic)2.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.81 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.46 m³·mol⁻¹ChemAxon
Polarizability19.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID168882  
KEGG Compound IDNot Available
BioCyc IDCPD-12774  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound194654  
PDB IDNot Available
ChEBI ID85785  
Good Scents IDNot Available
References
General References
  1. De Laurentis W, Khim L, Anderson JL, Adam A, Johnson KA, Phillips RS, Chapman SK, van Pee KH, Naismith JH: The second enzyme in pyrrolnitrin biosynthetic pathway is related to the heme-dependent dioxygenase superfamily. Biochemistry. 2007 Oct 30;46(43):12393-404. doi: 10.1021/bi7012189. Epub 2007 Oct  9. [PubMed:17924666  ] 
  2. Wynands I, van Pee KH: A novel halogenase gene from the pentachloropseudilin producer Actinoplanes sp. ATCC 33002 and detection of in vitro halogenase activity. FEMS Microbiol Lett. 2004 Aug 15;237(2):363-7. doi: 10.1016/j.femsle.2004.06.053. [PubMed:15321684  ] 
  3. Burd VN, Van Pee KH: Halogenating enzymes in the biosynthesis of antibiotics. Biochemistry (Mosc). 2003 Oct;68(10):1132-5. doi: 10.1023/a:1026362729567. [PubMed:14616084  ] 
  4. LOTUS database [Link]