MiMeDB: Showing metabocard for Phenazine-1-carboxylic acid (MMDBc0008900)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:35:21 UTC

Update Date

2025-10-07 16:05:31 UTC

Metabolite ID

MMDBc0008900

Metabolite Identification

Common Name

Phenazine-1-carboxylic acid

Description

Phenazine-1-carboxylic acid is a member of the phenazine chemical class, recognized as a significant metabolite in various microbial species. This compound has garnered attention for its role as a biopesticide, notably registered in China under the name 'Shenqinmycin', and is produced efficiently by engineered strains of Pseudomonas chlororaphis from corn stover hydrolysates (PMID:41016559 ). Additionally, PCA is utilized in advanced sensor systems for simultaneous detection of multiple biological markers, including uric acid and interleukin-6 (PMID:40894038 ). It is identified as a unique metabolite of Pseudomonas aeruginosa alongside other phenazine derivatives (PMID:40848493 ). The compound serves as a precursor for the synthesis of 2-hydroxyphenazine, which exhibits enhanced antifungal activity against Gaeumannomyces graminis (PMID:40542515 ). Furthermore, phenazine-1-carboxylic acid's production can be influenced by genetic mutations in Pseudomonas strains, indicating its importance in microbial metabolism (PMID:40415130 ). Its widespread use in agriculture is attributed to its excellent antimicrobial properties, making it a valuable asset in the development of bio-fungicides (PMID:40240404 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171519332D          

 17 19  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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
    1.4289   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
 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
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  4 17  2  0  0  0  0
  8 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008900

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=C2N=C3C=CC=CC3=NC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H8N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H,(H,16,17)

> <INCHI_KEY>
JGCSKOVQDXEQHI-UHFFFAOYSA-N

> <FORMULA>
C13H8N2O2

> <MOLECULAR_WEIGHT>
224.219

> <EXACT_MASS>
224.058577506

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.543328827597264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
phenazine-1-carboxylic acid

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
2.7178386860000003

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6761394004143413

> <JCHEM_PKA_STRONGEST_BASIC>
0.8347918313549745

> <JCHEM_POLAR_SURFACE_AREA>
63.08

> <JCHEM_REFRACTIVITY>
60.412800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenazine-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

Synonyms

Value	Source
1-Carboxylic acid phenazine	ChEBI
1-Carboxyphenazine	ChEBI
1-Phenazinecarboxylic acid	ChEBI
Phenazin-1-carbonsaeure	ChEBI
Phenazinecarboxylic acid	ChEBI
1-Carboxylate phenazine	Generator
1-Phenazinecarboxylate	Generator
Phenazinecarboxylate	Generator
Phenazine-1-carboxylate	Generator

Molecular Formula

C₁₃H₈N₂O₂

Average Mass

224.219

Monoisotopic Mass

224.058577506

IUPAC Name

phenazine-1-carboxylic acid

Traditional Name

phenazine-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C2N=C3C=CC=CC3=NC2=CC=C1

InChI Identifier

InChI=1S/C13H8N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H,(H,16,17)

InChI Key

JGCSKOVQDXEQHI-UHFFFAOYSA-N

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
Pyrazine
Benzenoid
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
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:62412 )
monocarboxylic acid (CHEBI:62412 )
aromatic carboxylic acid (CHEBI:62412 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	1.59	ALOGPS
logP	2.72	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.08 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.41 m³·mol⁻¹	ChemAxon
Polarizability	22.54 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

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	110.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	34.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	329.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	577.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	467.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	320.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1824.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	97.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	465.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	257.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	254.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	198.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	109.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	184.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	509.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	250.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	280.4
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1358.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	851.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Phenazine-1-carboxylic acid_TMS_1	C[Si](C)(C)OC(=O)C1=CC=CC2=NC3=CC=CC=C3N=C12	standard non polar	2025-10-23	1909.54
Gas Chromatography	Phenazine-1-carboxylic acid_TMS_1	C[Si](C)(C)OC(=O)C1=CC=CC2=NC3=CC=CC=C3N=C12	standard polar	2025-10-23	2054.35

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human	Metabolic reconstruction
Bacteria	Proteobacteria	1	Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-9522

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

62412

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Phenazine-1-carboxylic acid (MMDBc0008900)

MOL for #<Metabolite:0x00007f2e3110b920>

3D MOL for #<Metabolite:0x00007f2e3110b920>

3D SDF for #<Metabolite:0x00007f2e3110b920>

3D-SDF for #<Metabolite:0x00007f2e3110b920>

PDB for #<Metabolite:0x00007f2e3110b920>

3D PDB for #<Metabolite:0x00007f2e3110b920>

SMILES for #<Metabolite:0x00007f2e3110b920>

INCHI for #<Metabolite:0x00007f2e3110b920>

Structure for #<Metabolite:0x00007f2e3110b920>

3D Structure for #<Metabolite:0x00007f2e3110b920>