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Showing NP-Card for Pyoluteorin (NP0140243)

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Record Information
Version2.0
Created at2022-06-29 21:15:59 UTC
Updated at2022-06-29 21:16:00 UTC
NP-MRD IDNP0140243
Secondary Accession NumbersNone
Natural Product Identification
Common NamePyoluteorin
Description2-(4,5-Dichloro-1H-pyrrole-2-carbonyl)benzene-1,3-diol belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. Pyoluteorin is found in Pseudomonas chlororaphis and Pseudomonas fluorescens. 2-(4,5-Dichloro-1H-pyrrole-2-carbonyl)benzene-1,3-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0140243 (Pyoluteorin)


  Mrv1533004171500392D          

 17 18  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408   -3.1745    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -3.1745    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -1.7224    0.0000 N   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  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
M  END
Download

3D MOL for NP0140243 (Pyoluteorin)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
    0.5805   -2.2693   -0.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4463   -0.9943   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6790   -0.2707    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2429    0.7632   -0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3984    1.1747    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5007    2.4321   -0.5062 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    0.4125    1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8990    0.5420    2.3040 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5095   -0.4332    1.2152 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8898   -0.4680   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308   -1.2644   -0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4426   -2.5047   -1.3952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1191   -0.8183   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.3878   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966    1.1370    0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2538    0.7410    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140    1.5926    1.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099    1.1330   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -1.1264    2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1550   -3.0349   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8344   -1.4505   -1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5709    0.6962   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9043    2.0863    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147    1.5362    1.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 10  2  0
 10  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
 10 11  1  0
  9  3  1  0
 12 20  1  0
 13 21  1  0
 14 22  1  0
 15 23  1  0
 17 24  1  0
  4 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0140243 (Pyoluteorin)


  Mrv1533004171500392D          

 17 18  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408   -3.1745    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460   -3.1745    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -1.7224    0.0000 N   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  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC(O)=C1C(=O)C1=CC(Cl)=C(Cl)N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H7Cl2NO3/c12-5-4-6(14-11(5)13)10(17)9-7(15)2-1-3-8(9)16/h1-4,14-16H

> <INCHI_KEY>
JPGWTZORMBTNMF-UHFFFAOYSA-N

> <FORMULA>
C11H7Cl2NO3

> <MOLECULAR_WEIGHT>
272.08

> <EXACT_MASS>
270.9802985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
24.44857563540095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4,5-dichloro-1H-pyrrole-2-carbonyl)benzene-1,3-diol

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
4.048453454666667

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.229426221814538

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.932182667368085

> <JCHEM_PKA_STRONGEST_BASIC>
-6.919053426863582

> <JCHEM_POLAR_SURFACE_AREA>
73.32

> <JCHEM_REFRACTIVITY>
64.8423

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4,5-dichloro-1H-pyrrole-2-carbonyl)benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0140243 (Pyoluteorin)

Download
PDB for NP0140243 (Pyoluteorin)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.247  -3.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.771  -4.680   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       5.676  -5.926   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       3.231  -4.680   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       2.326  -5.926   0.000  0.00  0.00          Cl+0
HETATM   17  N   UNK     0       2.755  -3.215   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

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3D PDB for NP0140243 (Pyoluteorin)
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SMILES for NP0140243 (Pyoluteorin)
OC1=CC=CC(O)=C1C(=O)C1=CC(Cl)=C(Cl)N1
Download
INCHI for NP0140243 (Pyoluteorin)
InChI=1S/C11H7Cl2NO3/c12-5-4-6(14-11(5)13)10(17)9-7(15)2-1-3-8(9)16/h1-4,14-16H
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H7Cl2NO3
Average Mass272.0800 Da
Monoisotopic Mass270.98030 Da
IUPAC Name2-(4,5-dichloro-1H-pyrrole-2-carbonyl)benzene-1,3-diol
Traditional Name2-(4,5-dichloro-1H-pyrrole-2-carbonyl)benzene-1,3-diol
CAS Registry NumberNot Available
SMILES
OC1=CC=CC(O)=C1C(=O)C1=CC(Cl)=C(Cl)N1
InChI Identifier
InChI=1S/C11H7Cl2NO3/c12-5-4-6(14-11(5)13)10(17)9-7(15)2-1-3-8(9)16/h1-4,14-16H
InChI KeyJPGWTZORMBTNMF-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
Pseudomonas chlororaphisLOTUS Database
Pseudomonas fluorescensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAryl-phenylketones  
Alternative Parents
Substituents
  • Aryl-phenylketone
    • 

  • Benzoyl
    • 

  • Resorcinol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Aryl chloride
    • 

  • Aryl halide
    • 

  • Monocyclic benzene moiety
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organonitrogen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP3.58ALOGPS
logP4.05ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.93ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.84 m³·mol⁻¹ChemAxon
Polarizability24.45 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound33137  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available