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Showing NP-Card for 4-Phenylpyridine (NP0047556)

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Record Information
Version2.0
Created at2022-03-17 20:42:06 UTC
Updated at2022-03-17 20:42:06 UTC
NP-MRD IDNP0047556
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Phenylpyridine
Description4-Phenylpyridine, also known as 4-aza-1,1'-biphenyl or cyperquat, belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond. The compound and related derivatives have attracted interest as precursors to highly fluorescent metal complexes of possible value as organic light emitting diodes (OLEDs). 4-Phenylpyridine is a very strong basic compound (based on its pKa). 2-Phenylpyridine is an organic compound with the formula C6H5C5H4N. Outside of the human body, 4-Phenylpyridine has been detected, but not quantified in, a few different foods, such as herbs and spices, sweet oranges, and tea. This could make 4-phenylpyridine a potential biomarker for the consumption of these foods (III) and Platinum. It is a colourless viscous liquid. 4-Phenylpyridine is found in Citrus sinensis. The compound is prepared by the reaction of phenyl lithium with pyridine:C6H5Li + C5H5N → C6H5-C5H4N + LiHThe reaction of iridium trichloride with 2-phenylpyridine proceeds via cyclometallation to give the chloride-bridged complex:4 C6H5-C5H4N + 2 IrCl3(H2O)3 → Ir2Cl2(C6H4-C5H4N)4 + 4 HClThis complex can be converted to the pictured tris(cyclometallated) derivative.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047556 (4-Phenylpyridine)


  Mrv1652304272018332D          

 12 13  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4 10  2  0  0  0  0
  5 10  1  0  0  0  0
  6  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for NP0047556 (4-Phenylpyridine)

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3D SDF for NP0047556 (4-Phenylpyridine)

  Mrv1652304272018332D          

 12 13  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8876    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4 10  2  0  0  0  0
  5 10  1  0  0  0  0
  6  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1=CC=C(C=C1)C1=CC=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H9N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-9H

> <INCHI_KEY>
JVZRCNQLWOELDU-UHFFFAOYSA-N

> <FORMULA>
C11H9N

> <MOLECULAR_WEIGHT>
155.1959

> <EXACT_MASS>
155.073499293

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.225373968489674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-phenylpyridine

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.4027987510000006

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.07993829938984

> <JCHEM_POLAR_SURFACE_AREA>
12.89

> <JCHEM_REFRACTIVITY>
49.0373

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-phenylpyridine

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047556 (4-Phenylpyridine)
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PDB for NP0047556 (4-Phenylpyridine)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -6.160   0.000   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    8   11                                                       
CONECT    7    9   11                                                       
CONECT    8    6   12                                                       
CONECT    9    7   12                                                       
CONECT   10    4    5   11                                                  
CONECT   11    6    7   10                                                  
CONECT   12    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0047556 (4-Phenylpyridine)
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SMILES for NP0047556 (4-Phenylpyridine)
C1=CC=C(C=C1)C1=CC=NC=C1
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INCHI for NP0047556 (4-Phenylpyridine)
InChI=1S/C11H9N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-9H
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Synonyms
ValueSource
4-Phenyl-pyridineHMDB
1-Methyl-4-phenylpyridiniumHMDB
4-Aza-1,1'-biphenylHMDB
CyperquatHMDB
N-Methyl-4-phenylpyridineHMDB
p-PhenylpyridineHMDB
Phenyl-pyridineHMDB
Chemical FormulaC11H9N
Average Mass155.1959 Da
Monoisotopic Mass155.07350 Da
IUPAC Name4-phenylpyridine
Traditional Name4-phenylpyridine
CAS Registry Number939-23-1
SMILES
C1=CC=C(C=C1)C1=CC=NC=C1
InChI Identifier
InChI=1S/C11H9N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-9H
InChI KeyJVZRCNQLWOELDU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus sinensisLOTUS Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassPhenylpyridines  
Direct ParentPhenylpyridines  
Alternative Parents
Substituents
  • 4-phenylpyridine
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP2.4ALOGPS
logP2.4ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)5.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.04 m³·mol⁻¹ChemAxon
Polarizability17.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033123  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011123  
KNApSAcK IDNot Available
Chemspider ID13062  
KEGG Compound IDC11310  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Phenylpyridine  
METLIN IDNot Available
PubChem Compound13651  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available