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Showing NP-Card for phenazine (NP0263947)

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Record Information
Version2.0
Created at2022-09-08 07:18:05 UTC
Updated at2022-09-08 07:18:05 UTC
NP-MRD IDNP0263947
Secondary Accession NumbersNone
Natural Product Identification
Common Namephenazine
DescriptionPhenazine, also known as acridizine or azophenylene, 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. Phenazine is a moderately basic compound (based on its pKa). phenazine is found in Pseudomonas fluorescens, Streptomyces albidoflavus, Streptomyces aurantiogriseus, Streptomyces coelicolor and Streptomyces diastaticus. phenazine was first documented in 2014 (PMID: 24482022). An azaarene that is anthracene in which the carbon atoms at positions 9 and 10 are replaced by nitrogen atoms.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0263947 (phenazine)


  Mrv1533004271515312D          

 14 16  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
  1 14  1  0  0  0  0
M  END
Download

3D MOL for NP0263947 (phenazine)

     RDKit          3D

 22 24  0  0  0  0  0  0  0  0999 V2000
    3.6217   -0.2933    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4893    0.9799   -0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    1.4673   -0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839    0.7390   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380    1.2212   -0.5388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2675    0.5106   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5127    1.0499   -0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6221    0.2962   -0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -0.9721    0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2251   -1.4885    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846   -0.7585    0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1266   -1.2699    0.4698 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267   -0.5292    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -1.0543    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6080   -0.6957    0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460    1.5702   -0.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    2.4753   -0.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634    2.0691   -0.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5998    0.7292   -0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3906   -1.5199    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357   -2.4931    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -2.0334    0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 11  1  0
  4 13  1  0
  9 20  1  0
 10 21  1  0
 14 22  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  7 18  1  0
  8 19  1  0
M  END
Download

3D SDF for NP0263947 (phenazine)


  Mrv1533004271515312D          

 14 16  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263947

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1=CC2=NC3=CC=CC=C3N=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H8N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H

> <INCHI_KEY>
PCNDJXKNXGMECE-UHFFFAOYSA-N

> <FORMULA>
C12H8N2

> <MOLECULAR_WEIGHT>
180.21

> <EXACT_MASS>
180.068748266

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
19.416342862044853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
phenazine

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
3.0602557779999993

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.7024626869731345

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
53.1566

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenazine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0263947 (phenazine)

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PDB for NP0263947 (phenazine)
HEADER    PROTEIN                                 27-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    4   14                                                  
CONECT   14   13    1                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

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3D PDB for NP0263947 (phenazine)
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SMILES for NP0263947 (phenazine)
C1=CC2=NC3=CC=CC=C3N=C2C=C1
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INCHI for NP0263947 (phenazine)
InChI=1S/C12H8N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
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View in JSmol
Synonyms
ValueSource
9,10-DiazaanthraceneChEBI
AcridizineChEBI
AzophenyleneChEBI
Dibenzo-p-diazineChEBI
DibenzoparadiazineChEBI
DibenzopyrazineChEBI
Chemical FormulaC12H8N2
Average Mass180.2100 Da
Monoisotopic Mass180.06875 Da
IUPAC Namephenazine
Traditional Namephenazine
CAS Registry NumberNot Available
SMILES
C1=CC2=NC3=CC=CC=C3N=C2C=C1
InChI Identifier
InChI=1S/C12H8N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
InChI KeyPCNDJXKNXGMECE-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 fluorescensLOTUS Database
Streptomyces albidoflavusLOTUS Database
Streptomyces aurantiogriseusLOTUS Database
Streptomyces coelicolorLOTUS Database
Streptomyces diastaticusLOTUS Database
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
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.82ALOGPS
logP3.06ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity53.16 m³·mol⁻¹ChemAxon
Polarizability19.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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 IDCPD-12873  
BiGG IDNot Available
Wikipedia LinkPhenazine  
METLIN IDNot Available
PubChem Compound4757  
PDB IDNot Available
ChEBI ID36674  
Good Scents IDNot Available
References
General References
  1. Roy SK, Samanta S, Chowdhury NS, Mondal TK, Goswami S: Double C(arom)-H activation associated with etheral oxygen insertion to phenazine architecture in oxidisable ruthenium(III) complexes: a mechanistic insight. Chemistry. 2014 Mar 3;20(10):2712-7. doi: 10.1002/chem.201303932. Epub 2014 Jan  30. [PubMed:24482022  ] 
  2. LOTUS database [Link]