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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:17 UTC

Update Date

2023-02-21 17:19:08 UTC

HMDB ID

HMDB0029727

Secondary Accession Numbers

HMDB29727

Metabolite Identification

Common Name

5-Ethyl-2,3-dimethylpyrazine

Description

5-Ethyl-2,3-dimethylpyrazine 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. 5-Ethyl-2,3-dimethylpyrazine is a burnt and popcorn tasting compound. 5-Ethyl-2,3-dimethylpyrazine has been detected, but not quantified in, several different foods, such as herbs and spices, peppers (Capsicum annuum), red bell peppers (Capsicum annuum), yellow bell peppers (Capsicum annuum), and orange bell peppers (Capsicum annuum). This could make 5-ethyl-2,3-dimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Ethyl-2,3-dimethylpyrazine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dimethyl-5-ethylpyrazine	HMDB
2,3-Dimethyl-6-ethylpyrazine	HMDB
2-Ethyl-5,6-dimethylpyrazine	HMDB
5,6-Dimethyl-2-ethylpyrazine	HMDB
6-Ethyl-2,3-dimethylpyrazine	HMDB
Pyrazine, 6-ethyl-2,3-dimethyl	HMDB

Chemical Formula

C₈H₁₂N₂

Average Molecular Weight

136.1943

Monoisotopic Molecular Weight

136.100048394

IUPAC Name

5-ethyl-2,3-dimethylpyrazine

Traditional Name

5-ethyl-2,3-dimethylpyrazine

CAS Registry Number

15707-34-3

SMILES

CCC1=CN=C(C)C(C)=N1

InChI Identifier

InChI=1S/C8H12N2/c1-4-8-5-9-6(2)7(3)10-8/h5H,4H2,1-3H3

InChI Key

CIBKSMZEVHTQLG-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: HMDB0029727)
Cytoplasm (HMDB: HMDB0029727)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029727)

Source

Endogenous

Endogenous (HMDB: HMDB0029727)

Plant

Plant (HMDB: HMDB0029727)

Exogenous

Food

Food (HMDB: HMDB0029727)

Vegetable

Fruit vegetable

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029727)

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	190.00 to 191.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1473 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.457 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.7 g/L	ALOGPS
logP	1.59	ALOGPS
logP	0.63	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Basic)	1.93	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	40.15 m³·mol⁻¹	ChemAxon
Polarizability	15.91 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]+	128.863	31661259
DarkChem	[M-H]-	128.459	31661259
DeepCCS	[M+H]+	131.472	30932474
DeepCCS	[M-H]-	127.643	30932474
DeepCCS	[M-2H]-	164.908	30932474
DeepCCS	[M+Na]+	140.28	30932474
AllCCS	[M+H]+	129.3	32859911
AllCCS	[M+H-H2O]+	124.8	32859911
AllCCS	[M+NH4]+	133.6	32859911
AllCCS	[M+Na]+	134.9	32859911
AllCCS	[M-H]-	131.8	32859911
AllCCS	[M+Na-2H]-	133.7	32859911
AllCCS	[M+HCOO]-	135.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Ethyl-2,3-dimethylpyrazine	CCC1=CN=C(C)C(C)=N1	1443.2	Standard polar	33892256
5-Ethyl-2,3-dimethylpyrazine	CCC1=CN=C(C)C(C)=N1	1038.6	Standard non polar	33892256
5-Ethyl-2,3-dimethylpyrazine	CCC1=CN=C(C)C(C)=N1	1087.4	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 - 5-Ethyl-2,3-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-4900000000-22e55154249f1b10ce98	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-6900000000-5335ef535918acd18a65	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 - 5-Ethyl-2,3-dimethylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-31b3c7038f7fd07dd14a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 20V, Positive-QTOF	splash10-000i-1900000000-f341ca722f51a7e0d497	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 40V, Positive-QTOF	splash10-0udl-9100000000-2562c086ae5b21fc6893	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-b3068bdcb75424315b4e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 20V, Negative-QTOF	splash10-000i-0900000000-f2a74d1dfead25b7bbd3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 40V, Negative-QTOF	splash10-066r-8900000000-6d5ddfae1694282f7d00	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-ac299646e14f1770c4b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 20V, Positive-QTOF	splash10-000i-8900000000-4c98b257125fd5404f23	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 40V, Positive-QTOF	splash10-0pw9-9000000000-37446a0b572e59eb4626	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-560d709635c029cd0cba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 20V, Negative-QTOF	splash10-000i-4900000000-b52ad37937380afd2652	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Ethyl-2,3-dimethylpyrazine 40V, Negative-QTOF	splash10-001i-5900000000-5952a87013cc54fbdf97	2021-09-22	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB000923

KNApSAcK ID

Not Available

Chemspider ID

25554

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

27460

PDB ID

Not Available

ChEBI ID

254553

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1551711

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 5-Ethyl-2,3-dimethylpyrazine (HMDB0029727)

MOL for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

3D MOL for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

3D SDF for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

3D-SDF for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

PDB for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

3D PDB for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

SMILES for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

INCHI for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

Structure for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

3D Structure for HMDB0029727 (5-Ethyl-2,3-dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra