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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:51 UTC

Update Date

2023-02-21 17:23:06 UTC

HMDB ID

HMDB0033123

Secondary Accession Numbers

HMDB33123

Metabolite Identification

Common Name

4-Phenylpyridine

Description

4-Phenylpyridine 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. 4-Phenylpyridine has been detected, but not quantified in, several different foods, such as herbal tea, herbs and spices, teas (Camellia sinensis), red tea, and green tea. This could make 4-phenylpyridine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Phenylpyridine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
p-Phenylpyridine	MeSH
4-Phenyl-pyridine	ChEMBL, HMDB
1-Methyl-4-phenylpyridinium	HMDB
4-Aza-1,1'-biphenyl	HMDB
Cyperquat	HMDB
N-Methyl-4-phenylpyridine	HMDB
Phenyl-pyridine	HMDB

Chemical Formula

C₁₁H₉N

Average Molecular Weight

155.1959

Monoisotopic Molecular Weight

155.073499293

IUPAC Name

4-phenylpyridine

Traditional Name

4-phenylpyridine

CAS Registry Number

939-23-1

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 Key

JVZRCNQLWOELDU-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033123)
Cell membrane (HMDB: HMDB0033123)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033123)

Source

Exogenous

Exogenous (HMDB: HMDB0033123)

Food

Food (HMDB: HMDB0033123)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033123)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033123)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	77 - 78 °C	Not Available
Boiling Point	281.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	441.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.59	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.4 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	5.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.04 m³·mol⁻¹	ChemAxon
Polarizability	17.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.398	31661259
DarkChem	[M-H]-	131.26	31661259
DeepCCS	[M+H]+	137.423	30932474
DeepCCS	[M-H]-	134.971	30932474
DeepCCS	[M-2H]-	170.724	30932474
DeepCCS	[M+Na]+	145.226	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.3	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	133.5	32859911
AllCCS	[M+Na-2H]-	134.1	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.73 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2807 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1488.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	351.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	306.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	416.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	315.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	933.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	103.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	934.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	454.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	300.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	45.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Phenylpyridine	C1=CC=C(C=C1)C1=CC=NC=C1	2304.6	Standard polar	33892256
4-Phenylpyridine	C1=CC=C(C=C1)C1=CC=NC=C1	1460.7	Standard non polar	33892256
4-Phenylpyridine	C1=CC=C(C=C1)C1=CC=NC=C1	1474.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Phenylpyridine EI-B (Non-derivatized)	splash10-0a4i-4900000000-10e14e0d648ed0b56707	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Phenylpyridine EI-B (Non-derivatized)	splash10-0a4i-4900000000-10e14e0d648ed0b56707	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenylpyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-85259f8d9ea92af450b3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenylpyridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenylpyridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Phenylpyridine LC-ESI-qTof , Positive-QTOF	splash10-0a6r-0900000000-fe67755f3a6f726d71c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Phenylpyridine , positive-QTOF	splash10-0a6r-0900000000-fe67755f3a6f726d71c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Phenylpyridine 61V, Positive-QTOF	splash10-0a4i-0900000000-8c62ca28955e3c08c14d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 10V, Positive-QTOF	splash10-0a4i-0900000000-6b78b624d077f063474e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 20V, Positive-QTOF	splash10-0a4i-0900000000-5be9b32d9d3e3491c5bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 40V, Positive-QTOF	splash10-0zi0-3900000000-e98a858afea13ed6626a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 10V, Negative-QTOF	splash10-0udi-0900000000-e3a046f2fa89c2924dc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 20V, Negative-QTOF	splash10-0udi-0900000000-e4d968bfc2db7ca205da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 40V, Negative-QTOF	splash10-0ufr-1900000000-a28ea482d9fd45c1de3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 10V, Negative-QTOF	splash10-0udi-0900000000-dad8c928447125c7059a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 20V, Negative-QTOF	splash10-0udi-0900000000-24c2b0ba340c0ccf2467	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 40V, Negative-QTOF	splash10-0ufr-1900000000-fef72f47c86d6eda27a8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 10V, Positive-QTOF	splash10-0a4i-0900000000-c96b9f679f0b9bcb2557	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 20V, Positive-QTOF	splash10-0a4i-0900000000-c942db8b89d28e9d26f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenylpyridine 40V, Positive-QTOF	splash10-0fb9-2900000000-b670de498d6dc479d25f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011123

KNApSAcK ID

Not Available

Chemspider ID

13062

KEGG Compound ID

C11310

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Phenylpyridine

METLIN ID

Not Available

PubChem Compound

13651

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1206701

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Phenylpyridine (HMDB0033123)

MOL for HMDB0033123 (4-Phenylpyridine)

3D MOL for HMDB0033123 (4-Phenylpyridine)

3D SDF for HMDB0033123 (4-Phenylpyridine)

3D-SDF for HMDB0033123 (4-Phenylpyridine)

PDB for HMDB0033123 (4-Phenylpyridine)

3D PDB for HMDB0033123 (4-Phenylpyridine)

SMILES for HMDB0033123 (4-Phenylpyridine)

INCHI for HMDB0033123 (4-Phenylpyridine)

Structure for HMDB0033123 (4-Phenylpyridine)

3D Structure for HMDB0033123 (4-Phenylpyridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra