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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:52:50 UTC

Update Date

2023-02-21 17:22:50 UTC

HMDB ID

HMDB0032946

Secondary Accession Numbers

HMDB32946

Metabolite Identification

Common Name

3,5-Diethyl-2-methylpyrazine

Description

3,5-Diethyl-2-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. 3,5-Diethyl-2-methylpyrazine is a baked, meaty, and nutty tasting compound. 3,5-Diethyl-2-methylpyrazine has been detected, but not quantified in, several different foods, such as herbs and spices, red tea, arabica coffees (Coffea arabica), potatos (Solanum tuberosum), and robusta coffees (Coffea canephora). This could make 3,5-diethyl-2-methylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,5-Diethyl-2-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
2,6-Diethyl-3-methylpyrazine	HMDB
2,6-Diethyl-5-methylpyrazine	HMDB
2-Methyl-3,5-diethylpyrazine	HMDB
3,5-Diethyl-2-methyl-pyrazine	HMDB
FEMA 3916	HMDB

Chemical Formula

C₉H₁₄N₂

Average Molecular Weight

150.2209

Monoisotopic Molecular Weight

150.115698458

IUPAC Name

3,5-diethyl-2-methylpyrazine

Traditional Name

3,5-diethyl-2-methylpyrazine

CAS Registry Number

18138-05-1

SMILES

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

InChI Identifier

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

InChI Key

MRWLZECVHMHMGI-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: HMDB0032946)
Cytoplasm (HMDB: HMDB0032946)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032946)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032946)

Source

Exogenous

Food

Food (HMDB: HMDB0032946)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Tea

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032946)
Coffea (HMDB: HMDB0032946)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032946)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032946)

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	8.25 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.33	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	1.78	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	17.84 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]+	133.987	31661259
DarkChem	[M-H]-	133.028	31661259
DeepCCS	[M+H]+	139.267	30932474
DeepCCS	[M-H]-	135.44	30932474
DeepCCS	[M-2H]-	173.039	30932474
DeepCCS	[M+Na]+	148.578	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.4	32859911
AllCCS	[M+NH4]+	137.1	32859911
AllCCS	[M+Na]+	138.3	32859911
AllCCS	[M-H]-	136.1	32859911
AllCCS	[M+Na-2H]-	137.7	32859911
AllCCS	[M+HCOO]-	139.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Diethyl-2-methylpyrazine	CCC1=NC(CC)=C(C)N=C1	1500.1	Standard polar	33892256
3,5-Diethyl-2-methylpyrazine	CCC1=NC(CC)=C(C)N=C1	1122.4	Standard non polar	33892256
3,5-Diethyl-2-methylpyrazine	CCC1=NC(CC)=C(C)N=C1	1162.8	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 - 3,5-Diethyl-2-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe0-4900000000-7dfd5059b806b9913a11	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Diethyl-2-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udj-5900000000-e351b2869d2a3bef9fc0	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 - 3,5-Diethyl-2-methylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-f8431c3a22ebb66c147d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 20V, Positive-QTOF	splash10-0udi-1900000000-d6286d5d2ebc8e606da7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 40V, Positive-QTOF	splash10-0ldl-9100000000-1d21829519459086d94f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-2b969cd3de5d15c89f52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 20V, Negative-QTOF	splash10-0002-1900000000-b0fd1457f9eea8fc7537	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 40V, Negative-QTOF	splash10-0q33-9800000000-752283a9b48ed6c37b8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-50a674f3d9a955d9216b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 20V, Negative-QTOF	splash10-0002-1900000000-3f41588ad2198ee49cba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 40V, Negative-QTOF	splash10-0f6t-9700000000-3329cc1ccc94109a3e34	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-7dff70ee86f025608d41	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 20V, Positive-QTOF	splash10-0uk9-1900000000-be0984aff94f1b9b7335	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Diethyl-2-methylpyrazine 40V, Positive-QTOF	splash10-015a-9300000000-8df0d8661298c0844178	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

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19754154	details

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

FDB010931

KNApSAcK ID

Not Available

Chemspider ID

26887

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

28906

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1301661

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 3,5-Diethyl-2-methylpyrazine (HMDB0032946)

MOL for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

3D MOL for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

3D SDF for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

3D-SDF for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

PDB for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

3D PDB for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

SMILES for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

INCHI for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

Structure for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

3D Structure for HMDB0032946 (3,5-Diethyl-2-methylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra