NP-MRD: Showing NP-Card for Phenazine-1-carboxamide (NP0023162)

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Record Information

Version

2.0

Created at

2021-01-06 08:16:45 UTC

Updated at

2021-07-15 17:41:00 UTC

NP-MRD ID

NP0023162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenazine-1-carboxamide

Provided By

NPAtlas

Description

Phenazine-1-carboxamide is also known as 1-carbamoylphenazine or oxychloraphin. Phenazine-1-carboxamide is found in Pseudomonas aeruginosa. Phenazine-1-carboxamide was first documented in 1996 (PMID: 8666196). Based on a literature review very few articles have been published on phenazine-1-carboxamide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105393D          

 26 28  0  0  0  0            999 V2000
   -3.9409   -1.6875    0.0769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526   -1.4338   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944   -2.4066   -0.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -0.0901    0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    0.9838    0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482    2.2740    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918    2.5081    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1440    1.4562    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    1.6419    0.1938 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0014    0.5803   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.7951   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193   -0.2550   -0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763   -1.5179   -0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3325   -1.7515   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907   -0.6889   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512   -0.8855   -0.1523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    0.1636    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932   -2.2764    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703   -1.2845   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911    0.7763    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    3.0635    0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344    3.5129    0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599    1.7903   -0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009   -0.1325   -0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -2.3720   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -2.7640   -0.6388 H   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17  4  1  0  0  0  0
 17  8  1  0  0  0  0
 15 10  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6 21  1  0  0  0  0
  7 22  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 14 26  1  0  0  0  0
M  END


  Mrv1652306242105393D          

 26 28  0  0  0  0            999 V2000
   -3.9409   -1.6875    0.0769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526   -1.4338   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944   -2.4066   -0.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -0.0901    0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    0.9838    0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482    2.2740    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918    2.5081    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1440    1.4562    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    1.6419    0.1938 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0014    0.5803   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.7951   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193   -0.2550   -0.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763   -1.5179   -0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3325   -1.7515   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907   -0.6889   -0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512   -0.8855   -0.1523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    0.1636    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932   -2.2764    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703   -1.2845   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911    0.7763    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    3.0635    0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344    3.5129    0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599    1.7903   -0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009   -0.1325   -0.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -2.3720   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -2.7640   -0.6388 H   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17  4  1  0  0  0  0
 17  8  1  0  0  0  0
 15 10  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6 21  1  0  0  0  0
  7 22  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 14 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C(=O)C1=C([H])C([H])=C([H])C2=NC3=C([H])C([H])=C([H])C([H])=C3N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H9N3O/c14-13(17)8-4-3-7-11-12(8)16-10-6-2-1-5-9(10)15-11/h1-7H,(H2,14,17)

> <INCHI_KEY>
KPZYYKDXZKFBQU-UHFFFAOYSA-N

> <FORMULA>
C13H9N3O

> <MOLECULAR_WEIGHT>
223.235

> <EXACT_MASS>
223.074561922

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
23.217766047533946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
phenazine-1-carboxamide

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.9108960723333333

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.157018323809865

> <JCHEM_PKA_STRONGEST_BASIC>
1.31806993793219

> <JCHEM_POLAR_SURFACE_AREA>
68.87

> <JCHEM_REFRACTIVITY>
62.235000000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenazine-1-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

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  N   UNK     0      -3.941  -1.688   0.077  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.553  -1.434  -0.004  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.794  -2.407  -0.242  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.007  -0.090   0.180  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.831   0.984   0.441  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.348   2.274   0.622  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.992   2.508   0.541  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.144   1.456   0.281  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.187   1.642   0.194  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.001   0.580  -0.064  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.363   0.795  -0.150  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.219  -0.255  -0.409  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.676  -1.518  -0.580  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.333  -1.752  -0.500  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.491  -0.689  -0.239  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.151  -0.886  -0.152  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.653   0.164   0.103  0.00  0.00           C+0
HETATM   18  H   UNK     0      -4.293  -2.276   0.853  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.570  -1.285  -0.632  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.891   0.776   0.501  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.070   3.063   0.825  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.634   3.513   0.683  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.760   1.790  -0.012  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.301  -0.133  -0.486  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.314  -2.372  -0.786  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.925  -2.764  -0.639  0.00  0.00           H+0
CONECT    1    2   18   19                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   10                                                  
CONECT   16   15   17                                                       
CONECT   17   16    4    8                                                  
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    5                                                            
CONECT   21    6                                                            
CONECT   22    7                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1-Carbamoylphenazine	ChEBI
1-Phenazinecarboxamide	ChEBI
Oxychloraphin	ChEBI
Oxychlororaphine	ChEBI
Phenazine-1-carboxyamide	ChEBI
Phenazine-1-carboxylic acid amide	ChEBI
Phenazine-1-carboxylate amide	Generator
PA-1-ca CPD	MeSH

Chemical Formula

C₁₃H₉N₃O

Average Mass

223.2350 Da

Monoisotopic Mass

223.07456 Da

IUPAC Name

phenazine-1-carboxamide

Traditional Name

phenazine-1-carboxamide

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CC=CC2=NC3=CC=CC=C3N=C12

InChI Identifier

InChI=1S/C13H9N3O/c14-13(17)8-4-3-7-11-12(8)16-10-6-2-1-5-9(10)15-11/h1-7H,(H2,14,17)

InChI Key

KPZYYKDXZKFBQU-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
Pseudomonas aeruginosa	NPAtlas	8666196

Chemical Taxonomy

Description

This compound 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
Azacycle
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenazines (CHEBI:62240 )
monocarboxylic acid amide (CHEBI:62240 )
aromatic amide (CHEBI:62240 )

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	2.03	ALOGPS
logP	1.91	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.16	ChemAxon
pKa (Strongest Basic)	1.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.87 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.24 m³·mol⁻¹	ChemAxon
Polarizability	23.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004963

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

107380

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

62240

Good Scents ID

Not Available

References

General References

Stead P, Rudd BA, Bradshaw H, Noble D, Dawson MJ: Induction of phenazine biosynthesis in cultures of Pseudomonas aeruginosa by L-N-(3-oxohexanoyl)homoserine lactone. FEMS Microbiol Lett. 1996 Jun 15;140(1):15-22. doi: 10.1111/j.1574-6968.1996.tb08308.x. [PubMed:8666196 ]

Showing NP-Card for Phenazine-1-carboxamide (NP0023162)

MOL for NP0023162 (Phenazine-1-carboxamide)

3D MOL for NP0023162 (Phenazine-1-carboxamide)

3D SDF for NP0023162 (Phenazine-1-carboxamide)

3D-SDF for NP0023162 (Phenazine-1-carboxamide)

PDB for NP0023162 (Phenazine-1-carboxamide)

3D PDB for NP0023162 (Phenazine-1-carboxamide)

SMILES for NP0023162 (Phenazine-1-carboxamide)

INCHI for NP0023162 (Phenazine-1-carboxamide)

Structure for NP0023162 (Phenazine-1-carboxamide)

3D Structure for NP0023162 (Phenazine-1-carboxamide)