NP-MRD: Showing NP-Card for 1,6-phenazinedicarboxylic acid (NP0283979)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 11:28:54 UTC

Updated at

2022-09-09 11:28:54 UTC

NP-MRD ID

NP0283979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,6-phenazinedicarboxylic acid

Description

Phenazine-1,6-dicarboxylic acid, also known as 1,6-phenazinedicarboxylate, 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. 1,6-phenazinedicarboxylic acid is found in Apis cerana, Burkholderia cepacia, Dermacoccus abyssi, Pseudomonas chlororaphis, Pseudomonas fluorescens and Streptomyces cinnamonensis. 1,6-phenazinedicarboxylic acid was first documented in 2001 (PMID: 11562236). Phenazine-1,6-dicarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 20448892) (PMID: 21090727) (PMID: 12139622) (PMID: 19053436).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041410012D          

 20 22  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    4.2868    3.3000    0.0000 C   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
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 16 11  2  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  2  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=CC2=NC3=C(C=CC=C3N=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8N2O4/c17-13(18)7-3-1-5-9-11(7)16-10-6-2-4-8(14(19)20)12(10)15-9/h1-6H,(H,17,18)(H,19,20)

> <INCHI_KEY>
MJALVONLCNWZHK-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O4

> <MOLECULAR_WEIGHT>
268.2243

> <EXACT_MASS>
268.048406754

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
25.72312634691739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
phenazine-1,6-dicarboxylic acid

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
2.3754215939999996

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2370065670577692

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.348690087376712

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0855619811075266

> <JCHEM_POLAR_SURFACE_AREA>
100.38000000000001

> <JCHEM_REFRACTIVITY>
67.669

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,6-phenazinedicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11   13                                                  
CONECT    8    4   12   14                                                  
CONECT    9    5   11   15                                                  
CONECT   10    6   12   16                                                  
CONECT   11    7    9   16                                                  
CONECT   12    8   10   15                                                  
CONECT   13    7   17   18                                                  
CONECT   14    8   19   20                                                  
CONECT   15    9   12                                                       
CONECT   16   10   11                                                       
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
1,6-Phenazinedicarboxylic acid	ChEBI
Phenazine-1,6-dicarboxylate	Kegg
1,6-Phenazinedicarboxylate	Generator

Chemical Formula

C₁₄H₈N₂O₄

Average Mass

268.2243 Da

Monoisotopic Mass

268.04841 Da

IUPAC Name

phenazine-1,6-dicarboxylic acid

Traditional Name

1,6-phenazinedicarboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=CC2=NC3=C(C=CC=C3N=C12)C(O)=O

InChI Identifier

InChI=1S/C14H8N2O4/c17-13(18)7-3-1-5-9-11(7)16-10-6-2-4-8(14(19)20)12(10)15-9/h1-6H,(H,17,18)(H,19,20)

InChI Key

MJALVONLCNWZHK-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633
Burkholderia cepacia	LOTUS Database	35616633
Dermacoccus abyssi	LOTUS Database	35616633
Pseudomonas chlororaphis	LOTUS Database	35616633
Pseudomonas fluorescens	LOTUS Database	35616633
Streptomyces cinnamonensis	LOTUS Database	35616633

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
Dicarboxylic acid or derivatives
Pyrazine
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenazines (CHEBI:70231 )

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	1.15	ALOGPS
logP	2.38	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.67 m³·mol⁻¹	ChemAxon
Polarizability	25.72 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C12119

BioCyc ID

CPD-12872

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193025

PDB ID

Not Available

ChEBI ID

70231

Good Scents ID

Not Available

References

General References

Abdel-Mageed WM, Milne BF, Wagner M, Schumacher M, Sandor P, Pathom-aree W, Goodfellow M, Bull AT, Horikoshi K, Ebel R, Diederich M, Fiedler HP, Jaspars M: Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment. Org Biomol Chem. 2010 May 21;8(10):2352-62. doi: 10.1039/c001445a. Epub 2010 Mar 18. [PubMed:20448892 ]
Abdelfattah MS, Kazufumi T, Ishibashi M: Izumiphenazines A-C: isolation and structure elucidation of phenazine derivatives from Streptomyces sp. IFM 11204. J Nat Prod. 2010 Dec 27;73(12):1999-2002. doi: 10.1021/np100400t. Epub 2010 Nov 23. [PubMed:21090727 ]
McDonald M, Mavrodi DV, Thomashow LS, Floss HG: Phenazine biosynthesis in Pseudomonas fluorescens: branchpoint from the primary shikimate biosynthetic pathway and role of phenazine-1,6-dicarboxylic acid. J Am Chem Soc. 2001 Sep 26;123(38):9459-60. doi: 10.1021/ja011243+. [PubMed:11562236 ]
Giddens SR, Feng Y, Mahanty HK: Characterization of a novel phenazine antibiotic gene cluster in Erwinia herbicola Eh1087. Mol Microbiol. 2002 Aug;45(3):769-83. doi: 10.1046/j.1365-2958.2002.03048.x. [PubMed:12139622 ]
Ahuja EG, Janning P, Mentel M, Graebsch A, Breinbauer R, Hiller W, Costisella B, Thomashow LS, Mavrodi DV, Blankenfeldt W: PhzA/B catalyzes the formation of the tricycle in phenazine biosynthesis. J Am Chem Soc. 2008 Dec 17;130(50):17053-61. doi: 10.1021/ja806325k. [PubMed:19053436 ]
LOTUS database [Link]

Showing NP-Card for 1,6-phenazinedicarboxylic acid (NP0283979)

MOL for NP0283979 (1,6-phenazinedicarboxylic acid)

3D MOL for NP0283979 (1,6-phenazinedicarboxylic acid)

3D SDF for NP0283979 (1,6-phenazinedicarboxylic acid)

3D-SDF for NP0283979 (1,6-phenazinedicarboxylic acid)

PDB for NP0283979 (1,6-phenazinedicarboxylic acid)

3D PDB for NP0283979 (1,6-phenazinedicarboxylic acid)

SMILES for NP0283979 (1,6-phenazinedicarboxylic acid)

INCHI for NP0283979 (1,6-phenazinedicarboxylic acid)

Structure for NP0283979 (1,6-phenazinedicarboxylic acid)

3D Structure for NP0283979 (1,6-phenazinedicarboxylic acid)