NP-MRD: Showing NP-Card for Pyocyanine (NP0008835)

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Record Information

Version

1.0

Created at

2020-12-09 06:19:52 UTC

Updated at

2021-07-15 17:01:33 UTC

NP-MRD ID

NP0008835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyocyanine

Provided By

NPAtlas

Description

Pyocyanin belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring. Pyocyanin 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. Pyocyanine is found in Bacillus. It was first documented in 1899 (PMID: 19866929). Based on a literature review a significant number of articles have been published on Pyocyanin (PMID: 27322205) (PMID: 27517959) (PMID: 27559393) (PMID: 27940577).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

 26 28  0  0  0  0            999 V2000
    0.1656    2.3174    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232    0.9135    0.1906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977    0.3401   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309    1.1214    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    0.5772   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5968   -0.7624   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103   -1.6026   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6400   -2.8459   -0.7959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -1.0734   -0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -1.8432   -0.3625 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.2824   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930   -2.0390   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452   -1.5149    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891   -0.1812    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4422    0.6156    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    0.0811    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3771    2.7983   -0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147    2.8164    0.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4949    2.5328    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    2.1691    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    1.2541   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942   -1.1537   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -3.0981   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -2.1180    0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    0.2974    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5652    1.6807    0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  7  9  1  0  0  0  0
  9 10  2  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16  2  1  0  0  0  0
  9  3  1  0  0  0  0
 16 11  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
M  END


  Mrv1652306242106303D          

 26 28  0  0  0  0            999 V2000
    0.1656    2.3174    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232    0.9135    0.1906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977    0.3401   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309    1.1214    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    0.5772   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5968   -0.7624   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103   -1.6026   -0.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6400   -2.8459   -0.7959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -1.0734   -0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -1.8432   -0.3625 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.2824   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930   -2.0390   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452   -1.5149    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891   -0.1812    0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4422    0.6156    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    0.0811    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3771    2.7983   -0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147    2.8164    0.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4949    2.5328    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    2.1691    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    1.2541   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942   -1.1537   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -3.0981   -0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -2.1180    0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    0.2974    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5652    1.6807    0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  7  9  1  0  0  0  0
  9 10  2  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16  2  1  0  0  0  0
  9  3  1  0  0  0  0
 16 11  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C2N(C3=C([H])C([H])=C([H])C(=O)C3=NC2=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H10N2O/c1-15-10-6-3-2-5-9(10)14-13-11(15)7-4-8-12(13)16/h2-8H,1H3

> <INCHI_KEY>
YNCMLFHHXWETLD-UHFFFAOYSA-N

> <FORMULA>
C13H10N2O

> <MOLECULAR_WEIGHT>
210.2313

> <EXACT_MASS>
210.079312952

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.351109778119586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-1,5-dihydrophenazin-1-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.4985149463333327

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.7791664245141825

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
68.05930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyocyanine

> <JCHEM_VEBER_RULE>
1

$$$$

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  C   UNK     0       0.166   2.317   0.452  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.123   0.914   0.191  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.098   0.340  -0.039  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.231   1.121   0.002  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.489   0.577  -0.223  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.597  -0.762  -0.490  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.510  -1.603  -0.546  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.640  -2.846  -0.796  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.259  -1.073  -0.324  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.161  -1.843  -0.363  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.040  -1.282  -0.137  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.193  -2.039  -0.164  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.445  -1.515   0.063  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.589  -0.181   0.332  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.442   0.616   0.367  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.192   0.081   0.138  0.00  0.00           C+0
HETATM   17  H   UNK     0      -0.377   2.798  -0.428  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.115   2.816   0.482  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.495   2.533   1.327  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.125   2.169   0.217  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.337   1.254  -0.175  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.594  -1.154  -0.660  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.139  -3.098  -0.371  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.358  -2.118   0.040  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.546   0.297   0.520  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.565   1.681   0.586  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3   16                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10    3                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15    2   11                                                  
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23   12                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Pyocyanine	HMDB
Pyocyanin	ChEBI

Chemical Formula

C₁₃H₁₀N₂O

Average Mass

210.2313 Da

Monoisotopic Mass

210.07931 Da

IUPAC Name

5-methyl-1,5-dihydrophenazin-1-one

Traditional Name

pyocyanine

CAS Registry Number

Not Available

SMILES

CN1C2=CC=CC=C2N=C2C(=O)C=CC=C12

InChI Identifier

InChI=1S/C13H10N2O/c1-15-10-6-3-2-5-9(10)14-13-11(15)7-4-8-12(13)16/h2-8H,1H3

InChI Key

YNCMLFHHXWETLD-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
Bacillus	NPAtlas	19866929

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Phenazines and derivatives

Alternative Parents

Substituents

Phenazine
Benzenoid
Pyrazine
Heteroaromatic compound
Vinylogous amide
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.9	ALOGPS
logP	2.5	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.06 m³·mol⁻¹	ChemAxon
Polarizability	22.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA000489

HMDB ID

HMDB0256934

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018654

Chemspider ID

6558

KEGG Compound ID

Not Available

BioCyc ID

CPD-12847

BiGG ID

Not Available

Wikipedia Link

Pyocyanin

METLIN ID

Not Available

PubChem Compound

6817

PDB ID

Not Available

ChEBI ID

8653

Good Scents ID

Not Available

References

General References

Jordan EO: BACILLUS PYOCYANEUS AND ITS PIGMENTS. J Exp Med. 1899 Sep 1;4(5-6):627-47. doi: 10.1084/jem.4.5-6.627. [PubMed:19866929 ]
Jagmann N, Bleicher V, Busche T, Kalinowski J, Philipp B: The guanidinobutyrase GbuA is essential for the alkylquinolone-regulated pyocyanin production during parasitic growth of Pseudomonas aeruginosa in co-culture with Aeromonas hydrophila. Environ Microbiol. 2016 Oct;18(10):3550-3564. doi: 10.1111/1462-2920.13419. Epub 2016 Jul 20. [PubMed:27322205 ]
Hall S, McDermott C, Anoopkumar-Dukie S, McFarland AJ, Forbes A, Perkins AV, Davey AK, Chess-Williams R, Kiefel MJ, Arora D, Grant GD: Cellular Effects of Pyocyanin, a Secreted Virulence Factor of Pseudomonas aeruginosa. Toxins (Basel). 2016 Aug 9;8(8). pii: toxins8080236. doi: 10.3390/toxins8080236. [PubMed:27517959 ]
Morkunas B, Gal B, Galloway WR, Hodgkinson JT, Ibbeson BM, Tan YS, Welch M, Spring DR: Discovery of an inhibitor of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells. Beilstein J Org Chem. 2016 Jul 11;12:1428-33. doi: 10.3762/bjoc.12.137. eCollection 2016. [PubMed:27559393 ]
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Showing NP-Card for Pyocyanine (NP0008835)

MOL for NP0008835 (Pyocyanine)

3D MOL for NP0008835 (Pyocyanine)

3D SDF for NP0008835 (Pyocyanine)

3D-SDF for NP0008835 (Pyocyanine)

PDB for NP0008835 (Pyocyanine)

3D PDB for NP0008835 (Pyocyanine)

SMILES for NP0008835 (Pyocyanine)

INCHI for NP0008835 (Pyocyanine)

Structure for NP0008835 (Pyocyanine)

3D Structure for NP0008835 (Pyocyanine)