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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 21:11:52 UTC

Update Date

2023-02-21 17:25:06 UTC

HMDB ID

HMDB0036132

Secondary Accession Numbers

HMDB36132

Metabolite Identification

Common Name

2,5-Diethyl-3-methylpyrazine

Description

2,5-Diethyl-3-methylpyrazine 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-Diethyl-3-methylpyrazine is a hazelnut, meaty, and toasted tasting compound. 2,5-Diethyl-3-methylpyrazine has been detected, but not quantified in, several different foods, such as robusta coffees (Coffea canephora), cocoa beans (Theobroma cacao), arabica coffees (Coffea arabica), potatos (Solanum tuberosum), and coffee and coffee products. This could make 2,5-diethyl-3-methylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,5-Diethyl-3-methylpyrazine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,6-Diethyl-2-methylpyrazine	HMDB
FEMA 3915	HMDB

Chemical Formula

C₉H₁₄N₂

Average Molecular Weight

150.2209

Monoisotopic Molecular Weight

150.115698458

IUPAC Name

2,5-diethyl-3-methylpyrazine

Traditional Name

2,5-diethyl-3-methylpyrazine

CAS Registry Number

32736-91-7

SMILES

CCC1=NC(C)=C(CC)N=C1

InChI Identifier

InChI=1S/C9H14N2/c1-4-8-6-10-9(5-2)7(3)11-8/h6H,4-5H2,1-3H3

InChI Key

RJIREWQSLPRZFG-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: HMDB0036132)
Cytoplasm (HMDB: HMDB0036132)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036132)

Source

Exogenous

Exogenous (HMDB: HMDB0036132)

Food

Food (HMDB: HMDB0036132)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

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)

Not Available

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036132)

Biological role

Nutrient (HMDB: HMDB0036132)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	95.00 °C. @ 14.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.966 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.3 g/L	ALOGPS
logP	2.17	ALOGPS
logP	1.33	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	1.86	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	2	ChemAxon
Refractivity	44.77 m³·mol⁻¹	ChemAxon
Polarizability	17.87 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]+	133.544	31661259
DarkChem	[M-H]-	132.632	31661259
DeepCCS	[M+H]+	139.515	30932474
DeepCCS	[M-H]-	135.688	30932474
DeepCCS	[M-2H]-	173.269	30932474
DeepCCS	[M+Na]+	148.807	30932474
AllCCS	[M+H]+	133.4	32859911
AllCCS	[M+H-H2O]+	129.0	32859911
AllCCS	[M+NH4]+	137.6	32859911
AllCCS	[M+Na]+	138.8	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.6	32859911
AllCCS	[M+HCOO]-	140.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Diethyl-3-methylpyrazine	CCC1=NC(C)=C(CC)N=C1	1491.3	Standard polar	33892256
2,5-Diethyl-3-methylpyrazine	CCC1=NC(C)=C(CC)N=C1	1120.4	Standard non polar	33892256
2,5-Diethyl-3-methylpyrazine	CCC1=NC(C)=C(CC)N=C1	1155.8	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 - 2,5-Diethyl-3-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fer-4900000000-a4881a1232423ff628d9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Diethyl-3-methylpyrazine 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 - 2,5-Diethyl-3-methylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-b77844985e0dce63bae5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 20V, Positive-QTOF	splash10-0udi-1900000000-855460aa14c1a298ad40	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 40V, Positive-QTOF	splash10-0ldl-9100000000-356e8f7208816082caf1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-b5064df868cfc4568100	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 20V, Negative-QTOF	splash10-0002-1900000000-c86d74a4bbfdcd311164	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 40V, Negative-QTOF	splash10-0gir-9700000000-a52303c20e265ab3f034	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-7dff70ee86f025608d41	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 20V, Positive-QTOF	splash10-0uk9-2900000000-bcdd5c42eee2d6934b83	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 40V, Positive-QTOF	splash10-067i-9100000000-edc28184f7955909d140	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-50a674f3d9a955d9216b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 20V, Negative-QTOF	splash10-0002-1900000000-2bef8cefc0fdff80c4e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Diethyl-3-methylpyrazine 40V, Negative-QTOF	splash10-0002-4900000000-bbb0c47519f64ed19ff4	2021-09-22	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

FDB014981

KNApSAcK ID

Not Available

Chemspider ID

33311

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

36225

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1301651

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-Diethyl-3-methylpyrazine (HMDB0036132)

MOL for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

3D MOL for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

3D SDF for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

3D-SDF for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

PDB for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

3D PDB for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

SMILES for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

INCHI for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

Structure for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

3D Structure for HMDB0036132 (2,5-Diethyl-3-methylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra