Np mrd loader

Record Information
Version2.0
Created at2020-12-09 06:19:52 UTC
Updated at2021-07-15 17:01:33 UTC
NP-MRD IDNP0008835
Secondary Accession NumbersNone
Natural Product Identification
Common NamePyocyanine
Provided ByNPAtlasNPAtlas Logo
DescriptionPyocyanin 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. Pyocyanine was first documented in 1899 (PMID: 19866929). Based on a literature review a small amount of articles have been published on Pyocyanin (PMID: 27322205) (PMID: 27517959) (PMID: 27559393) (PMID: 27940577).
Structure
Thumb
Synonyms
ValueSource
PyocyanineHMDB
PyocyaninChEBI
Chemical FormulaC13H10N2O
Average Mass210.2313 Da
Monoisotopic Mass210.07931 Da
IUPAC Name5-methyl-1,5-dihydrophenazin-1-one
Traditional Namepyocyanine
CAS Registry NumberNot 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 KeyYNCMLFHHXWETLD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
BacillusNPAtlas
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentPhenazines 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 FrameworkAromatic heteropolycyclic 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
logP1.9ALOGPS
logP2.5ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.06 m³·mol⁻¹ChemAxon
Polarizability22.35 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA000489
HMDB IDHMDB0256934
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018654
Chemspider ID6558
KEGG Compound IDNot Available
BioCyc IDCPD-12847
BiGG IDNot Available
Wikipedia LinkPyocyanin
METLIN IDNot Available
PubChem Compound6817
PDB IDNot Available
ChEBI ID8653
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Costa KC, Glasser NR, Conway SJ, Newman DK: Pyocyanin degradation by a tautomerizing demethylase inhibits Pseudomonas aeruginosa biofilms. Science. 2017 Jan 13;355(6321):170-173. doi: 10.1126/science.aag3180. Epub 2016 Dec 8. [PubMed:27940577 ]