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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:15:41 UTC

Update Date

2023-02-21 17:28:49 UTC

HMDB ID

HMDB0041568

Secondary Accession Numbers

HMDB41568

Metabolite Identification

Common Name

2-Ethyl-5-methylpyrazine, 9CI, 8CI

Description

2-Ethyl-5-methylpyrazine, 9CI, 8CI, also known as 2,5-methylethylpyrazine or fema 3154, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. 2-Ethyl-5-methylpyrazine, 9CI, 8CI is a sweet and fruit tasting compound. 2-Ethyl-5-methylpyrazine, 9CI, 8CI has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make 2-ethyl-5-methylpyrazine, 9ci, 8CI a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Ethyl-5-methylpyrazine, 9CI, 8CI.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,5-Methylethylpyrazine	ChEBI
2-Ethyl-5-methyl-pyrazine	ChEBI
2-Methyl-5-ethylpyrazine	ChEBI
FEMA 3154	ChEBI
2-Ethyl-5-methyl pyrazine	HMDB
5-Ethyl-2-methylpyrazine	HMDB
Pyrazine, 5-ethyl-2-methyl	HMDB

Chemical Formula

C₇H₁₀N₂

Average Molecular Weight

122.171

Monoisotopic Molecular Weight

122.08439833

IUPAC Name

2-ethyl-5-methylpyrazine

Traditional Name

pyrazine, 2-ethyl-5-methyl-

CAS Registry Number

13360-64-0

SMILES

CCC1=NC=C(C)N=C1

InChI Identifier

InChI=1S/C7H10N2/c1-3-7-5-8-6(2)4-9-7/h4-5H,3H2,1-2H3

InChI Key

OXCKCFJIKRGXMM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
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

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041568)
Cytoplasm (HMDB: HMDB0041568)

Source

Exogenous

Exogenous (HMDB: HMDB0041568)

Food

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Fruit vegetable

Tuber

Potato (FooDB: FOOD00175)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Tea

Herb and spice

Herb

Fenugreek (FooDB: FOOD00186)

Snack

Tortilla chip (FooDB: FOOD00721)

Dish

Tex-mex cuisine

Taco (FooDB: FOOD00708)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Nut

Nuts (FooDB: FOOD00869)

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	170.83 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	4903 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.197 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	77.2 g/L	ALOGPS
logP	1.18	ALOGPS
logP	0.5	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Basic)	1.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.55 m³·mol⁻¹	ChemAxon
Polarizability	13.87 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]+	125.619	31661259
DarkChem	[M-H]-	123.807	31661259
DeepCCS	[M+H]+	127.589	30932474
DeepCCS	[M-H]-	124.076	30932474
DeepCCS	[M-2H]-	161.273	30932474
DeepCCS	[M+Na]+	136.351	30932474
AllCCS	[M+H]+	125.3	32859911
AllCCS	[M+H-H2O]+	120.5	32859911
AllCCS	[M+NH4]+	129.7	32859911
AllCCS	[M+Na]+	131.0	32859911
AllCCS	[M-H]-	127.7	32859911
AllCCS	[M+Na-2H]-	129.9	32859911
AllCCS	[M+HCOO]-	132.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ethyl-5-methylpyrazine, 9CI, 8CI	CCC1=CN=C(C)C=N1	1384.0	Standard polar	33892256
2-Ethyl-5-methylpyrazine, 9CI, 8CI	CCC1=CN=C(C)C=N1	955.6	Standard non polar	33892256
2-Ethyl-5-methylpyrazine, 9CI, 8CI	CCC1=CN=C(C)C=N1	1006.6	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-methylpyrazine, 9CI, 8CI GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-9500000000-94d4449a2511432b4306	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-7900000000-d0e9845ca4f9923b8ca1	2015-03-01	Not Available	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-methylpyrazine, 9CI, 8CI 10V, Positive-QTOF	splash10-00di-0900000000-0f1ebfef3c3c4ba34b25	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 20V, Positive-QTOF	splash10-00di-3900000000-68b911b860cdf5e41d2e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 40V, Positive-QTOF	splash10-0zfr-9100000000-bcbf96e68c1814339eed	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 10V, Negative-QTOF	splash10-00di-0900000000-576bd1c2212ee94f180b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 20V, Negative-QTOF	splash10-00di-1900000000-8e135cfc3128bf03a912	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 40V, Negative-QTOF	splash10-0k96-9200000000-edf3d57280040564bbdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 10V, Negative-QTOF	splash10-00di-0900000000-f917b7eaee02fed474b8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 20V, Negative-QTOF	splash10-00di-5900000000-61687b11501e6db083ff	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 40V, Negative-QTOF	splash10-0ufu-9000000000-29716227e80b83dfbb91	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 10V, Positive-QTOF	splash10-00di-2900000000-9b9183f715e350b8e1fd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 20V, Positive-QTOF	splash10-0apl-9000000000-ff9da68785eee1ca9273	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ethyl-5-methylpyrazine, 9CI, 8CI 40V, Positive-QTOF	splash10-0udl-9000000000-49e959bc68a04a0d6347	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

FDB004429

KNApSAcK ID

Not Available

Chemspider ID

24144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25915

PDB ID

Not Available

ChEBI ID

141542

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1120721

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-methylpyrazine, 9CI, 8CI (HMDB0041568)

MOL for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

3D MOL for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

3D SDF for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

3D-SDF for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

PDB for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

3D PDB for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

SMILES for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

INCHI for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

Structure for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

3D Structure for HMDB0041568 (2-Ethyl-5-methylpyrazine, 9CI, 8CI)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra