NP-MRD: Showing NP-Card for 5,10-dihydrophenazine-1-carboxylic acid (NP0291899)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 23:09:50 UTC

Updated at

2022-09-09 23:09:50 UTC

NP-MRD ID

NP0291899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,10-dihydrophenazine-1-carboxylic acid

Description

5,10-Dihydrophenazine-1-carboxylic acid 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. 5,10-dihydrophenazine-1-carboxylic acid is found in Apis cerana. 5,10-dihydrophenazine-1-carboxylic acid was first documented in 2011 (PMID: 21342470). 5,10-Dihydrophenazine-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22220635) (PMID: 23119011).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307102022202D          

 17 19  0  0  0  0            999 V2000
   -2.1495   -0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495   -1.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4350   -1.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7205   -1.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7205   -0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4350    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0061   -1.4472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083   -1.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083   -0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0061    0.2027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4228   -1.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -1.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1372   -0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4228    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4228    1.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1495    1.4472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    1.4330    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  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
  5 10  1  0  0  0  0
  8 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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0291899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=CC2=C1NC1=C(N2)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H10N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7,14-15H,(H,16,17)

> <INCHI_KEY>
RWCXEOMFBZOODX-UHFFFAOYSA-N

> <FORMULA>
C13H10N2O2

> <MOLECULAR_WEIGHT>
226.235

> <EXACT_MASS>
226.07422757

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.208528272301383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,10-dihydrophenazine-1-carboxylic acid

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.8374344586666664

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.501047405474784

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.517085998815669

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3034014663988137

> <JCHEM_POLAR_SURFACE_AREA>
61.36

> <JCHEM_REFRACTIVITY>
64.22860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,10-dihydrophenazine-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-20         0                                  
HETATM    1  C   UNK     0      -4.012  -0.391   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.012  -1.931   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.679  -2.701   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.345  -1.931   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.345  -0.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.679   0.378   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.011  -2.701   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.322  -1.931   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.322  -0.391   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.011   0.378   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.656  -2.701   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.989  -1.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.989  -0.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.656   0.378   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.656   1.918   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.012   2.701   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.345   2.675   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    5                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
5,10-Dihydrophenazine-1-carboxylate	Generator

Chemical Formula

C₁₃H₁₀N₂O₂

Average Mass

226.2350 Da

Monoisotopic Mass

226.07423 Da

IUPAC Name

5,10-dihydrophenazine-1-carboxylic acid

Traditional Name

5,10-dihydrophenazine-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=CC2=C1NC1=C(N2)C=CC=C1

InChI Identifier

InChI=1S/C13H10N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7,14-15H,(H,16,17)

InChI Key

RWCXEOMFBZOODX-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

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
Benzenoid
Vinylogous amide
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenazines (CHEBI:79181 )
aromatic carboxylic acid (CHEBI:79181 )

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	3.4	ALOGPS
logP	3.84	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.52	ChemAxon
pKa (Strongest Basic)	-0.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.23 m³·mol⁻¹	ChemAxon
Polarizability	23.21 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

24607254

KEGG Compound ID

Not Available

BioCyc ID

CPD-12874

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50986166

PDB ID

Not Available

ChEBI ID

79181

Good Scents ID

Not Available

References

General References

Zendah I, Riaz N, Nasr H, Frauendorf H, Schuffler A, Raies A, Laatsch H: Chromophenazines from the terrestrial Streptomyces sp. Ank 315. J Nat Prod. 2012 Jan 27;75(1):2-8. doi: 10.1021/np100818d. Epub 2012 Jan 5. [PubMed:22220635 ]
Zocher G, Saleh O, Heim JB, Herbst DA, Heide L, Stehle T: Structure-based engineering increased the catalytic turnover rate of a novel phenazine prenyltransferase. PLoS One. 2012;7(10):e48427. doi: 10.1371/journal.pone.0048427. Epub 2012 Oct 31. [PubMed:23119011 ]
Seeger K, Flinspach K, Haug-Schifferdecker E, Kulik A, Gust B, Fiedler HP, Heide L: The biosynthetic genes for prenylated phenazines are located at two different chromosomal loci of Streptomyces cinnamonensis DSM 1042. Microb Biotechnol. 2011 Mar;4(2):252-62. doi: 10.1111/j.1751-7915.2010.00234.x. Epub 2010 Dec 8. [PubMed:21342470 ]
LOTUS database [Link]

Showing NP-Card for 5,10-dihydrophenazine-1-carboxylic acid (NP0291899)

MOL for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

3D MOL for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

3D SDF for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

3D-SDF for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

PDB for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

3D PDB for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

SMILES for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

INCHI for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

Structure for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)

3D Structure for NP0291899 (5,10-dihydrophenazine-1-carboxylic acid)