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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:35:16 UTC

Update Date

2023-02-21 17:27:29 UTC

HMDB ID

HMDB0040041

Secondary Accession Numbers

HMDB40041

Metabolite Identification

Common Name

2-Ethyl-5-methylpyridine

Description

2-Ethyl-5-methylpyridine belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group. 2-Ethyl-5-methylpyridine has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, crustaceans, and robusta coffees (Coffea canephora). This could make 2-ethyl-5-methylpyridine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Ethyl-5-methylpyridine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Methyl-2-ethyl pyridine	HMDB
6-Ethyl-3-picoline	HMDB

Chemical Formula

C₈H₁₁N

Average Molecular Weight

121.1796

Monoisotopic Molecular Weight

121.089149357

IUPAC Name

2-ethyl-5-methylpyridine

Traditional Name

2-ethyl-5-methylpyridine

CAS Registry Number

18113-81-0

SMILES

CCC1=NC=C(C)C=C1

InChI Identifier

InChI=1S/C8H11N/c1-3-8-5-4-7(2)6-9-8/h4-6H,3H2,1-2H3

InChI Key

COHDGTRFTKHYSJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Methylpyridines

Direct Parent

Methylpyridines

Alternative Parents

Substituents

Methylpyridine
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

Extracellular (HMDB: HMDB0040041)
Cytoplasm (HMDB: HMDB0040041)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040041)

Source

Exogenous

Exogenous (HMDB: HMDB0040041)

Food

Food (HMDB: HMDB0040041)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Endogenous

Plant

Coffea (HMDB: HMDB0040041)

Animal

Animal (HMDB: HMDB0040041)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040041)

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	18030 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	32.1 g/L	ALOGPS
logP	2.17	ALOGPS
logP	2.1	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Basic)	6.06	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	38.16 m³·mol⁻¹	ChemAxon
Polarizability	14.47 Å³	ChemAxon
Number of Rings	1	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]+	126.26	31661259
DarkChem	[M-H]-	123.754	31661259
DeepCCS	[M+H]+	130.133	30932474
DeepCCS	[M-H]-	126.356	30932474
DeepCCS	[M-2H]-	163.674	30932474
DeepCCS	[M+Na]+	139.042	30932474
AllCCS	[M+H]+	122.2	32859911
AllCCS	[M+H-H2O]+	117.3	32859911
AllCCS	[M+NH4]+	126.8	32859911
AllCCS	[M+Na]+	128.1	32859911
AllCCS	[M-H]-	126.8	32859911
AllCCS	[M+Na-2H]-	128.9	32859911
AllCCS	[M+HCOO]-	131.2	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.	3.52 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6755 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.81 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	44.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	903.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	317.4 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	265.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	783.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	202.3 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	863.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	385.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	318.1 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	63.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethyl-5-methylpyridine	CCC1=NC=C(C)C=C1	1417.6	Standard polar	33892256
2-Ethyl-5-methylpyridine	CCC1=NC=C(C)C=C1	981.8	Standard non polar	33892256
2-Ethyl-5-methylpyridine	CCC1=NC=C(C)C=C1	1008.1	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 - 2-Ethyl-5-methylpyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-8900000000-b22a4784728dc164d25d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-5-methylpyridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-5-methylpyridine 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 - 2-Ethyl-5-methylpyridine 10V, Positive-QTOF	splash10-00di-0900000000-73699daa25d3df040ee8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 20V, Positive-QTOF	splash10-00di-2900000000-e2f8a629b55f8e493414	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 40V, Positive-QTOF	splash10-05mo-9200000000-34a0c70dcc82a8f12085	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 10V, Negative-QTOF	splash10-00di-0900000000-c75a39049689ae98b1e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 20V, Negative-QTOF	splash10-00di-0900000000-afa19d1cc4358f9717bd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 40V, Negative-QTOF	splash10-0f6x-9300000000-1625ce7e2c86fd82b189	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 10V, Negative-QTOF	splash10-00di-1900000000-bbf4344378f376692fea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 20V, Negative-QTOF	splash10-00di-6900000000-c2f5cc191cfdbcde12f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 40V, Negative-QTOF	splash10-0f6x-9000000000-2b7a51a592b2ff2e1205	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 10V, Positive-QTOF	splash10-00di-2900000000-b26f5259f37ea9dd681c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 20V, Positive-QTOF	splash10-0006-9200000000-e16cb264e382c3c00822	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyridine 40V, Positive-QTOF	splash10-00kf-9000000000-52b57c6fbca3885f6960	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Cytoplasm
Extracellular

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

FDB019728

KNApSAcK ID

Not Available

Chemspider ID

453160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519519

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1629241

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 2-Ethyl-5-methylpyridine (HMDB0040041)

MOL for HMDB0040041 (2-Ethyl-5-methylpyridine)

3D MOL for HMDB0040041 (2-Ethyl-5-methylpyridine)

3D SDF for HMDB0040041 (2-Ethyl-5-methylpyridine)

3D-SDF for HMDB0040041 (2-Ethyl-5-methylpyridine)

PDB for HMDB0040041 (2-Ethyl-5-methylpyridine)

3D PDB for HMDB0040041 (2-Ethyl-5-methylpyridine)

SMILES for HMDB0040041 (2-Ethyl-5-methylpyridine)

INCHI for HMDB0040041 (2-Ethyl-5-methylpyridine)

Structure for HMDB0040041 (2-Ethyl-5-methylpyridine)

3D Structure for HMDB0040041 (2-Ethyl-5-methylpyridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra