Np mrd loader

Record Information
Version2.0
Created at2021-06-21 00:38:56 UTC
Updated at2021-06-30 00:18:42 UTC
NP-MRD IDNP0043166
Secondary Accession NumbersNone
Natural Product Identification
Common Nametubermycin B
Provided ByJEOL DatabaseJEOL Logo
DescriptionPhenazine-1-carboxylic acid, also known as 1-phenazinecarboxylate or 1-carboxylic acid phenazine, 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-1-carboxylic acid 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. tubermycin B is found in Dermacoccus abyssi, Pseudomonas aurantiaca PB-St2, Pseudomonas chlororaphis, Pseudomonas fluorescens, Pseudomonas libanensis, Streptomyces anulatus, Streptomyces cinnamonensis, Streptomyces diastaticus and Streptomyces kebangsaanensis. tubermycin B was first documented in 2002 (PMID: 12458768). Based on a literature review a small amount of articles have been published on phenazine-1-carboxylic acid (PMID: 22138981) (PMID: 22724439) (PMID: 23636695).
Structure
Thumb
Synonyms
ValueSource
1-Carboxylic acid phenazineChEBI
1-CarboxyphenazineChEBI
1-Phenazinecarboxylic acidChEBI
Phenazin-1-carbonsaeureChEBI
Phenazinecarboxylic acidChEBI
1-Carboxylate phenazineGenerator
1-PhenazinecarboxylateGenerator
PhenazinecarboxylateGenerator
Phenazine-1-carboxylateGenerator
1-Phenazinecarboxylic acid, sodium saltMeSH
NRRL b-15132MeSH
Chemical FormulaC13H8N2O2
Average Mass224.2190 Da
Monoisotopic Mass224.05858 Da
IUPAC Namephenazine-1-carboxylic acid
Traditional Namephenazine-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)C1=C2N=C3C([H])=C([H])C([H])=C([H])C3=NC2=C([H])C([H])=C1[H]
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 KeyJGCSKOVQDXEQHI-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 100 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, chcl3, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dermacoccus abyssiLOTUS Database
Pseudomonas aurantiaca PB-St2JEOL database
    • Mehnaz, S., et al, J. Nat. Prod. 76, 135 (2013)
Pseudomonas chlororaphisLOTUS Database
Pseudomonas fluorescensLOTUS Database
Pseudomonas libanensisLOTUS Database
Streptomyces anulatusLOTUS Database
Streptomyces cinnamonensisLOTUS Database
Streptomyces diastaticusLOTUS Database
Streptomyces kebangsaanensisLOTUS 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
  • 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 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
logP1.59ALOGPS
logP2.72ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.08 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.41 m³·mol⁻¹ChemAxon
Polarizability22.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID85784
KEGG Compound IDNot Available
BioCyc IDCPD-9522
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound95069
PDB IDNot Available
ChEBI ID62412
Good Scents IDNot Available
References
General References
  1. Gebhardt K, Schimana J, Krastel P, Dettner K, Rheinheimer J, Zeeck A, Fiedler HP: Endophenazines A-D, new phenazine antibiotics from the arthropod associated endosymbiont Streptomyces anulatus. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2002 Sep;55(9):794-800. doi: 10.7164/antibiotics.55.794. [PubMed:12458768 ]
  2. Mavrodi DV, Mavrodi OV, Parejko JA, Bonsall RF, Kwak YS, Paulitz TC, Thomashow LS, Weller DM: Accumulation of the antibiotic phenazine-1-carboxylic acid in the rhizosphere of dryland cereals. Appl Environ Microbiol. 2012 Feb;78(3):804-12. doi: 10.1128/AEM.06784-11. Epub 2011 Dec 2. [PubMed:22138981 ]
  3. Puopolo G, Masi M, Raio A, Andolfi A, Zoina A, Cimmino A, Evidente A: Insights on the susceptibility of plant pathogenic fungi to phenazine-1-carboxylic acid and its chemical derivatives. Nat Prod Res. 2013;27(11):956-66. doi: 10.1080/14786419.2012.696257. Epub 2012 Jun 25. [PubMed:22724439 ]
  4. Du X, Li Y, Zhou W, Zhou Q, Liu H, Xu Y: Phenazine-1-carboxylic acid production in a chromosomally non-scar triple-deleted mutant Pseudomonas aeruginosa using statistical experimental designs to optimize yield. Appl Microbiol Biotechnol. 2013 Sep;97(17):7767-78. doi: 10.1007/s00253-013-4921-y. Epub 2013 May 1. [PubMed:23636695 ]
  5. Mehnaz, S., et al. (2013). Mehnaz, S., et al, J. Nat. Prod. 76, 135 (2013). J. Nat. Prod..