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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 20:14:46 UTC

Update Date

2023-02-21 17:24:45 UTC

HMDB ID

HMDB0035289

Secondary Accession Numbers

HMDB35289

Metabolite Identification

Common Name

2,5-Dimethylpyrazine

Description

2,5-Dimethylpyrazine, also known as fema 3272 or pyrazine,2,5-dimethyl, 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. 2,5-Dimethylpyrazine is a cocoa, grass, and medicinal tasting compound. 2,5-Dimethylpyrazine is found, on average, in the highest concentration within kohlrabis. 2,5-Dimethylpyrazine has also been detected, but not quantified, in several different foods, such as green vegetables, soy beans, asparagus, tortilla chips, and fenugreeks. This could make 2,5-dimethylpyrazine a potential biomarker for the consumption of these foods. It occurs naturally in baked potato, black or green tea, crispbread, French fries, malt, peated malt, raw asparagus, roasted barley, roasted filberts or pecans, squid, wheat bread, wild rice (Zizania aquatica), and wort. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including coffee and wines. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
25-Dimethyl-pyrazine	ChEMBL, HMDB
2, 5-Dimethylpyrazine	HMDB
2,5-Dimethyl pyrazine	HMDB
2,5-Dimethyl-1,4-diazine	HMDB
2,5-Dimethyl-pyrazine	HMDB
2,5-Dimethylparadiazine	HMDB
2,5-Dimethylpiazine	HMDB
FEMA 3272	HMDB
PYRAZINE,2,5-dimethyl	HMDB
2,6-Dimethylpyrazine	MeSH
2,5-DMP	MeSH

Chemical Formula

C₆H₈N₂

Average Molecular Weight

108.1411

Monoisotopic Molecular Weight

108.068748266

IUPAC Name

2,5-dimethylpyrazine

Traditional Name

2,5-dimethylpyrazine

CAS Registry Number

123-32-0

SMILES

CC1=CN=C(C)C=N1

InChI Identifier

InChI=1S/C6H8N2/c1-5-3-8-6(2)4-7-5/h3-4H,1-2H3

InChI Key

LCZUOKDVTBMCMX-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

Cellular substructure

Extracellular (HMDB: HMDB0035289)
Cytoplasm (HMDB: HMDB0035289)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0035289)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035289)

Source

Exogenous

Food

Food (HMDB: HMDB0035289)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Root vegetable

Kohlrabi (FooDB: FOOD00033)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Pulse

Bean

Mung bean (FooDB: FOOD00200)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Flat bread

Tortilla (FooDB: FOOD00709)

Cereals and cereal products (FooDB: FOOD00858)

Tea

Herb and spice

Herb

Fenugreek (FooDB: FOOD00186)
Soft-necked garlic (FooDB: FOOD00850)

Snack

Tortilla chip (FooDB: FOOD00721)

Dish

Tex-mex cuisine

Taco (FooDB: FOOD00708)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Aquatic origin

Mollusk

Mollusks (FooDB: FOOD00868)

Crustacean

Crustaceans (FooDB: FOOD00862)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0035289)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035289)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	15 °C	Not Available
Boiling Point	154.00 to 156.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	31970 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.63	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	184 g/L	ALOGPS
logP	0.62	ALOGPS
logP	-0.2	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Basic)	1.59	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	0	ChemAxon
Refractivity	30.93 m³·mol⁻¹	ChemAxon
Polarizability	11.91 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]+	121.646	31661259
DarkChem	[M-H]-	118.975	31661259
DeepCCS	[M+H]+	124.939	30932474
DeepCCS	[M-H]-	121.838	30932474
DeepCCS	[M-2H]-	158.604	30932474
DeepCCS	[M+Na]+	133.548	30932474
AllCCS	[M+H]+	121.6	32859911
AllCCS	[M+H-H2O]+	116.7	32859911
AllCCS	[M+NH4]+	126.2	32859911
AllCCS	[M+Na]+	127.6	32859911
AllCCS	[M-H]-	122.6	32859911
AllCCS	[M+Na-2H]-	125.3	32859911
AllCCS	[M+HCOO]-	128.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dimethylpyrazine	CC1=CN=C(C)C=N1	1305.1	Standard polar	33892256
2,5-Dimethylpyrazine	CC1=CN=C(C)C=N1	873.1	Standard non polar	33892256
2,5-Dimethylpyrazine	CC1=CN=C(C)C=N1	920.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylpyrazine EI-B (Non-derivatized)	splash10-052f-9300000000-081f35e3a3380ed2698b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylpyrazine EI-B (Non-derivatized)	splash10-052f-9300000000-081f35e3a3380ed2698b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-8900000000-2ada7e902f3d0e2b31e9	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethylpyrazine 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 - 2,5-Dimethylpyrazine , positive-QTOF	splash10-0a4i-4900000000-7e680d62ffa714f80403	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Positive-QTOF	splash10-0a4i-0900000000-9b8f23be4c9d8c94f24d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Positive-QTOF	splash10-0a4i-1900000000-b0964dc373b182b8f4c4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Positive-QTOF	splash10-0k9x-9000000000-dc3ffe8529561fb7b1cb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Negative-QTOF	splash10-0a4i-0900000000-032c8099a4abe667a4b9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Negative-QTOF	splash10-0a4i-0900000000-58fa248974f5ade4ee46	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Negative-QTOF	splash10-0a4i-7900000000-890f0c8c1e9a4f4bf6ff	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Negative-QTOF	splash10-0a4i-0900000000-1d4d8b4513a018558199	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Negative-QTOF	splash10-0a4i-5900000000-53b7bc7c89378de54482	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Negative-QTOF	splash10-0006-9000000000-d47061f2d3232fef8318	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 10V, Positive-QTOF	splash10-0a4i-3900000000-a2cd546c692d476da756	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 20V, Positive-QTOF	splash10-0a59-9400000000-696590183181b11c1a14	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylpyrazine 40V, Positive-QTOF	splash10-0udl-9000000000-c5a37365c74d0ec83537	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

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013954

KNApSAcK ID

C00052608

Chemspider ID

28992

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alkylpyrazine

METLIN ID

Not Available

PubChem Compound

31252

PDB ID

25R

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008141

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 2,5-Dimethylpyrazine (HMDB0035289)

MOL for HMDB0035289 (2,5-Dimethylpyrazine)

3D MOL for HMDB0035289 (2,5-Dimethylpyrazine)

3D SDF for HMDB0035289 (2,5-Dimethylpyrazine)

3D-SDF for HMDB0035289 (2,5-Dimethylpyrazine)

PDB for HMDB0035289 (2,5-Dimethylpyrazine)

3D PDB for HMDB0035289 (2,5-Dimethylpyrazine)

SMILES for HMDB0035289 (2,5-Dimethylpyrazine)

INCHI for HMDB0035289 (2,5-Dimethylpyrazine)

Structure for HMDB0035289 (2,5-Dimethylpyrazine)

3D Structure for HMDB0035289 (2,5-Dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra