NP-MRD: Showing NP-Card for 5,10-dihydrophenazine (NP0196676)

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Record Information

Version

2.0

Created at

2022-09-04 14:48:16 UTC

Updated at

2022-09-04 14:48:16 UTC

NP-MRD ID

NP0196676

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,10-dihydrophenazine

Description

5,10-Dihydrophenazine 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 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. 5,10-dihydrophenazine was first documented in 2020 (PMID: 34267405). Based on a literature review a significant number of articles have been published on 5,10-dihydrophenazine (PMID: 35608074) (PMID: 35543697) (PMID: 35259298) (PMID: 35197286) (PMID: 34652071) (PMID: 34432942).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216482D          

 14 16  0  0  0  0            999 V2000
    4.2868   -0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196676

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N1C2=CC=CC=C2NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H10N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8,13-14H

> <INCHI_KEY>
IVURTNNWJAPOML-UHFFFAOYSA-N

> <FORMULA>
C12H10N2

> <MOLECULAR_WEIGHT>
182.226

> <EXACT_MASS>
182.08439833

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.065901332307167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,10-dihydrophenazine

> <JCHEM_LOGP>
2.8798515506666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.90263697202372

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.90263697202372

> <JCHEM_PKA_STRONGEST_BASIC>
0.3872721118949002

> <JCHEM_POLAR_SURFACE_AREA>
24.06

> <JCHEM_REFRACTIVITY>
56.97240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,10-dihydrophenazine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    4                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₀N₂

Average Mass

182.2260 Da

Monoisotopic Mass

182.08440 Da

IUPAC Name

5,10-dihydrophenazine

Traditional Name

5,10-dihydrophenazine

CAS Registry Number

Not Available

SMILES

N1C2=CC=CC=C2NC2=CC=CC=C12

InChI Identifier

InChI=1S/C12H10N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8,13-14H

InChI Key

IVURTNNWJAPOML-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

Not Available

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
Azacycle
Secondary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.88	ChemAxon
pKa (Strongest Acidic)	17.9	ChemAxon
pKa (Strongest Basic)	0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	24.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.97 m³·mol⁻¹	ChemAxon
Polarizability	20.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

306259

KEGG Compound ID

Not Available

BioCyc ID

CPD-19109

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

345330

PDB ID

Not Available

ChEBI ID

132008

Good Scents ID

Not Available

References

General References

McCarthy B, Sartor S, Cole J, Damrauer N, Miyake GM: Solvent Effects and Side Reactions in Organocatalyzed Atom Transfer Radical Polymerization for Enabling the Controlled Polymerization of Acrylates Catalyzed by Diaryl Dihydrophenazines. Macromolecules. 2020 Nov 10;53(21):9208-9219. doi: 10.1021/acs.macromol.0c02245. Epub 2020 Oct 21. [PubMed:34267405 ]
Li H, Liu C, Wang X, Wang J, Li P, Xie G, Jiang Y, Chen R, Tao Y: Achieving Balanced Electrical Performance of Host Material through Dual N-P horizontal lineO Resonance Linkage for Efficient Electroluminescence. ACS Appl Mater Interfaces. 2022 Jun 8;14(22):25834-25841. doi: 10.1021/acsami.2c02745. Epub 2022 May 24. [PubMed:35608074 ]
Rall JM, Schorpp M, Keilwerth M, Maylander M, Friedmann C, Daub M, Richert S, Meyer K, Krossing I: Synthesis and Characterization of Stable Iron Pentacarbonyl Radical Cation Salts. Angew Chem Int Ed Engl. 2022 Aug 8;61(32):e202204080. doi: 10.1002/anie.202204080. Epub 2022 Jun 7. [PubMed:35543697 ]
Jin X, Li S, Guo L, Hua J, Qu DH, Su J, Zhang Z, Tian H: Interplay of Steric Effects and Aromaticity Reversals to Expand the Structural/Electronic Responses of Dihydrophenazines. J Am Chem Soc. 2022 Mar 23;144(11):4883-4896. doi: 10.1021/jacs.1c12610. Epub 2022 Mar 8. [PubMed:35259298 ]
Park H, Kwon G, Lee H, Lee K, Park SY, Kwon JE, Kang K, Kim SJ: In operando visualization of redox flow battery in membrane-free microfluidic platform. Proc Natl Acad Sci U S A. 2022 Mar 1;119(9):e2114947119. doi: 10.1073/pnas.2114947119. [PubMed:35197286 ]
Jiang WL, Huang B, Wu MX, Zhu YK, Zhao XL, Shi X, Yang HB: Post-Synthetic Modification of Metal-Organic Frameworks Bearing Phenazine Radical Cations for aza-Diels-Alder Reactions. Chem Asian J. 2021 Dec 1;16(23):3985-3992. doi: 10.1002/asia.202100883. Epub 2021 Oct 26. [PubMed:34652071 ]
Plater MJ, Harrison WTA: A Potential Iterative Approach to 1,4-Dihydro-N-Heteroacene Arrays. ChemistryOpen. 2022 Mar;11(3):e202100150. doi: 10.1002/open.202100150. Epub 2021 Aug 25. [PubMed:34432942 ]
Bhattacherjee A, Sneha M, Lewis-Borrell L, Amoruso G, Oliver TAA, Tyler J, Clark IP, Orr-Ewing AJ: Singlet and Triplet Contributions to the Excited-State Activities of Dihydrophenazine, Phenoxazine, and Phenothiazine Organocatalysts Used in Atom Transfer Radical Polymerization. J Am Chem Soc. 2021 Mar 10;143(9):3613-3627. doi: 10.1021/jacs.1c00279. Epub 2021 Feb 25. [PubMed:33629835 ]
van Vliet KM, van Leeuwen NS, Brouwer AM, de Bruin B: Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid. Beilstein J Org Chem. 2020 Mar 16;16:398-408. doi: 10.3762/bjoc.16.38. eCollection 2020. [PubMed:32273903 ]
Schorpp M, Heizmann T, Schmucker M, Rein S, Weber S, Krossing I: Synthesis and Application of a Perfluorinated Ammoniumyl Radical Cation as a Very Strong Deelectronator. Angew Chem Int Ed Engl. 2020 Jun 8;59(24):9453-9459. doi: 10.1002/anie.202002768. Epub 2020 Apr 24. [PubMed:32187797 ]
LOTUS database [Link]

Showing NP-Card for 5,10-dihydrophenazine (NP0196676)

MOL for NP0196676 (5,10-dihydrophenazine)

3D MOL for NP0196676 (5,10-dihydrophenazine)

3D SDF for NP0196676 (5,10-dihydrophenazine)

3D-SDF for NP0196676 (5,10-dihydrophenazine)

PDB for NP0196676 (5,10-dihydrophenazine)

3D PDB for NP0196676 (5,10-dihydrophenazine)

SMILES for NP0196676 (5,10-dihydrophenazine)

INCHI for NP0196676 (5,10-dihydrophenazine)

Structure for NP0196676 (5,10-dihydrophenazine)

3D Structure for NP0196676 (5,10-dihydrophenazine)