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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

2012-09-11 22:31:27 UTC

Update Date

2023-02-21 17:25:46 UTC

HMDB ID

HMDB0037282

Secondary Accession Numbers

HMDB37282

Metabolite Identification

Common Name

2-Methyl-5-vinylpyrazine

Description

2-Methyl-5-vinylpyrazine 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-Methyl-5-vinylpyrazine is a coffee tasting compound. 2-Methyl-5-vinylpyrazine has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), green vegetables, potatos (Solanum tuberosum), breakfast cereal, and cocoa beans (Theobroma cacao). This could make 2-methyl-5-vinylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methyl-5-vinylpyrazine.

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-Ethenyl-5-methyl pyrazine	HMDB
2-Ethenyl-5-methyl-pyrazine	HMDB
2-Ethenyl-5-methylpyrazine	HMDB
2-Ethenyl-5-methylpyrazine, 9ci	HMDB
2-Methyl-5-ethenylpyrazine	HMDB
2-Methyl-5-vinyl-pyrazine	HMDB
2-Vinyl-5-methylpyrazine	HMDB
Pyrazine, 2-vinyl,5-methyl	HMDB

Chemical Formula

C₇H₈N₂

Average Molecular Weight

120.1518

Monoisotopic Molecular Weight

120.068748266

IUPAC Name

2-ethenyl-5-methylpyrazine

Traditional Name

2-ethenyl-5-methylpyrazine

CAS Registry Number

13925-08-1

SMILES

CC1=CN=C(C=C)C=N1

InChI Identifier

InChI=1S/C7H8N2/c1-3-7-5-8-6(2)4-9-7/h3-5H,1H2,2H3

InChI Key

JASFBLBUHWKFBZ-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

Physiological effect

Organoleptic effect

Odor

Coffee

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037282)
Cytoplasm (HMDB: HMDB0037282)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037282)

Source

Exogenous

Exogenous (HMDB: HMDB0037282)

Food

Food (HMDB: HMDB0037282)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

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)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Not Available

Nutrient (HMDB: HMDB0037282)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	65.00 to 66.00 °C. @ 12.00 mm Hg	The Good Scents Company Information System
Water Solubility	6522 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.684 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	43.7 g/L	ALOGPS
logP	0.98	ALOGPS
logP	0.64	ChemAxon
logS	-0.44	ALOGPS
pKa (Strongest Basic)	1.37	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	35.57 m³·mol⁻¹	ChemAxon
Polarizability	13.14 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]+	124.969	31661259
DarkChem	[M-H]-	123.811	31661259
DeepCCS	[M+H]+	125.515	30932474
DeepCCS	[M-H]-	122.057	30932474
DeepCCS	[M-2H]-	159.182	30932474
DeepCCS	[M+Na]+	134.22	30932474
AllCCS	[M+H]+	124.0	32859911
AllCCS	[M+H-H2O]+	119.2	32859911
AllCCS	[M+NH4]+	128.6	32859911
AllCCS	[M+Na]+	129.9	32859911
AllCCS	[M-H]-	124.7	32859911
AllCCS	[M+Na-2H]-	126.8	32859911
AllCCS	[M+HCOO]-	129.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-5-vinylpyrazine	CC1=CN=C(C=C)C=N1	1478.5	Standard polar	33892256
2-Methyl-5-vinylpyrazine	CC1=CN=C(C=C)C=N1	990.1	Standard non polar	33892256
2-Methyl-5-vinylpyrazine	CC1=CN=C(C=C)C=N1	1031.2	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-Methyl-5-vinylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9400000000-a1af483a1e9259e790a0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-5-vinylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fk9-9700000000-7a3be426faa7f3f66f59	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-Methyl-5-vinylpyrazine 10V, Positive-QTOF	splash10-00di-0900000000-96d3ef70ac5a16f84b36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 20V, Positive-QTOF	splash10-00di-2900000000-ceca10705c8a1cda8464	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 40V, Positive-QTOF	splash10-0udi-9100000000-1adacc38f0ab8f59a9b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 10V, Negative-QTOF	splash10-014i-0900000000-8bdcb7b923f7f3ca7995	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 20V, Negative-QTOF	splash10-014i-1900000000-6f71c667b2ac56c90934	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 40V, Negative-QTOF	splash10-0f6x-9300000000-a9e0fa472c38d600316d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 10V, Negative-QTOF	splash10-014i-0900000000-dfae0f7e786381591011	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 20V, Negative-QTOF	splash10-00kf-9700000000-4eab50fdcc0dc618ea7b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 40V, Negative-QTOF	splash10-0udl-9100000000-93b2912b3d221ad1560c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 10V, Positive-QTOF	splash10-00di-2900000000-c0882b152bfa5a1f62c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 20V, Positive-QTOF	splash10-014l-9000000000-b6f314f0f292bce1f9fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-5-vinylpyrazine 40V, Positive-QTOF	splash10-0udr-9000000000-e66f3a5494af93dbba0a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

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

FDB016301

KNApSAcK ID

C00052650

Chemspider ID

24537

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26335

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035521

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-Methyl-5-vinylpyrazine (HMDB0037282)

MOL for HMDB0037282 (2-Methyl-5-vinylpyrazine)

3D MOL for HMDB0037282 (2-Methyl-5-vinylpyrazine)

3D SDF for HMDB0037282 (2-Methyl-5-vinylpyrazine)

3D-SDF for HMDB0037282 (2-Methyl-5-vinylpyrazine)

PDB for HMDB0037282 (2-Methyl-5-vinylpyrazine)

3D PDB for HMDB0037282 (2-Methyl-5-vinylpyrazine)

SMILES for HMDB0037282 (2-Methyl-5-vinylpyrazine)

INCHI for HMDB0037282 (2-Methyl-5-vinylpyrazine)

Structure for HMDB0037282 (2-Methyl-5-vinylpyrazine)

3D Structure for HMDB0037282 (2-Methyl-5-vinylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra