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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:08:32 UTC

Update Date

2021-09-26 22:51:18 UTC

HMDB ID

HMDB0243930

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Methyl-4-phenyl-2H-pyridine

Description

1-Methyl-4-phenyl-2H-pyridine, also known as 1 methyl 4 phenylpyridinium or cyperquat, belongs to the class of organic compounds known as dihydropyridines. Dihydropyridines are compounds containing a dihydropyridine moiety, which is a semi-saturated pyridine derivative with two double bonds. Based on a literature review very few articles have been published on 1-Methyl-4-phenyl-2H-pyridine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-methyl-4-phenyl-2h-pyridine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-Methyl-4-phenyl-2H-pyridine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0243930
HETATM    1  C1  UNL     1      -4.266   0.158   0.432  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.804   0.097   0.342  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.989  -0.189   1.446  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.672  -0.245   1.375  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.012  -0.006   0.111  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.488  -0.065   0.011  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.263  -0.349   1.117  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.648  -0.420   1.091  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.320  -0.199  -0.087  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.577   0.087  -1.206  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.173   0.154  -1.160  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.763   0.261  -0.916  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.228   0.346  -0.941  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.755  -0.275  -0.453  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.650  -0.252   1.363  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.508   1.252   0.428  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.524  -0.367   2.392  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.101  -0.473   2.271  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.800  -0.533   2.071  1.00  0.00           H  
HETATM   20  H7  UNL     1       4.238  -0.642   1.960  1.00  0.00           H  
HETATM   21  H8  UNL     1       5.409  -0.254  -0.106  1.00  0.00           H  
HETATM   22  H9  UNL     1       4.095   0.262  -2.137  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.624   0.381  -2.062  1.00  0.00           H  
HETATM   24  H11 UNL     1      -0.256   0.444  -1.881  1.00  0.00           H  
HETATM   25  H12 UNL     1      -2.562   1.322  -1.373  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.571  -0.498  -1.621  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   13
CONECT    3    4    4   17
CONECT    4    5   18
CONECT    5    6   12   12
CONECT    6    7    7   11
CONECT    7    8   19
CONECT    8    9    9   20
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   23
CONECT   12   13   24
CONECT   13   25   26
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1 Methyl 4 phenylpyridine	HMDB
1 Methyl 4 phenylpyridinium	HMDB
1 Methyl 4 phenylpyridinium chloride	HMDB
1 Methyl 4 phenylpyridinium ion	HMDB
1-Methyl-4-phenylpyridine	HMDB
1-Methyl-4-phenylpyridinium	HMDB
1-Methyl-4-phenylpyridinium chloride	HMDB
1-Methyl-4-phenylpyridinium ion	HMDB
Cyperquat	HMDB
N Methyl 4 phenylpyridine	HMDB
N-Methyl-4-phenylpyridine	HMDB
N-Methyl-4-phenylpyridinium	HMDB

Chemical Formula

C₁₂H₁₃N

Average Molecular Weight

171.243

Monoisotopic Molecular Weight

171.104799423

IUPAC Name

1-methyl-4-phenyl-1,2-dihydropyridine

Traditional Name

1-methyl-4-phenyl-2H-pyridine

CAS Registry Number

Not Available

SMILES

CN1CC=C(C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H13N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-9H,10H2,1H3

InChI Key

BRAJQLYTRXKQAW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyridines. Dihydropyridines are compounds containing a dihydropyridine moiety, which is a semi-saturated pyridine derivative with two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Dihydropyridines

Alternative Parents

Substituents

Dihydropyridine
Benzenoid
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Allylamine
Azacycle
Enamine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.18	ALOGPS
logP	2.36	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	7.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	57.56 m³·mol⁻¹	ChemAxon
Polarizability	20.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	136.984	30932474
DeepCCS	[M-H]-	134.48	30932474
DeepCCS	[M-2H]-	170.278	30932474
DeepCCS	[M+Na]+	145.242	30932474
AllCCS	[M+H]+	137.4	32859911
AllCCS	[M+H-H2O]+	132.8	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	141.9	32859911
AllCCS	[M+Na-2H]-	142.4	32859911
AllCCS	[M+HCOO]-	143.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3177 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1609.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	331.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	144.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	106.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	405.1 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	407.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1069.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	348.9 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	1177.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	340.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	267.0 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	17.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Methyl-4-phenyl-2H-pyridine	CN1CC=C(C=C1)C1=CC=CC=C1	2135.4	Standard polar	33892256
1-Methyl-4-phenyl-2H-pyridine	CN1CC=C(C=C1)C1=CC=CC=C1	1476.4	Standard non polar	33892256
1-Methyl-4-phenyl-2H-pyridine	CN1CC=C(C=C1)C1=CC=CC=C1	1471.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-1900000000-d51c7badf4daf91028da	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine 10V, Positive-QTOF	splash10-00di-0900000000-d73491e2a7183e5fee7c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine 20V, Positive-QTOF	splash10-00di-0900000000-8ab70698933140b7c0f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine 40V, Positive-QTOF	splash10-014i-1900000000-8c8142a161ba7a15b39c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine 10V, Negative-QTOF	splash10-00di-0900000000-41fe2c1901a626e07090	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine 20V, Negative-QTOF	splash10-00di-0900000000-41fe2c1901a626e07090	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Methyl-4-phenyl-2H-pyridine 40V, Negative-QTOF	splash10-00xr-0900000000-ac60973e80c7654c20df	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

163916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

188614

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1-Methyl-4-phenyl-2H-pyridine (HMDB0243930)

MOL for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

3D MOL for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

3D SDF for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

3D-SDF for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

PDB for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

3D PDB for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

SMILES for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

INCHI for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

Structure for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

3D Structure for HMDB0243930 (1-Methyl-4-phenyl-2H-pyridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra