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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:49:21 UTC

Update Date

2023-02-21 17:24:28 UTC

HMDB ID

HMDB0034892

Secondary Accession Numbers

HMDB34892

Metabolite Identification

Common Name

3-Ethyl-5-methyl-2-vinylpyrazine

Description

3-Ethyl-5-methyl-2-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. 3-Ethyl-5-methyl-2-vinylpyrazine is an earthy tasting compound. 3-Ethyl-5-methyl-2-vinylpyrazine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3-ethyl-5-methyl-2-vinylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Ethyl-5-methyl-2-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-3-ethyl-5-methylpyrazine, 9ci	HMDB

Chemical Formula

C₉H₁₂N₂

Average Molecular Weight

148.205

Monoisotopic Molecular Weight

148.100048394

IUPAC Name

2-ethenyl-3-ethyl-5-methylpyrazine

Traditional Name

2-ethenyl-3-ethyl-5-methylpyrazine

CAS Registry Number

181589-32-2

SMILES

CCC1=NC(C)=CN=C1C=C

InChI Identifier

InChI=1S/C9H12N2/c1-4-8-9(5-2)11-7(3)6-10-8/h4,6H,1,5H2,2-3H3

InChI Key

YSQNQOKRWIKETP-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: HMDB0034892)
Cytoplasm (HMDB: HMDB0034892)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034892)

Source

Exogenous

Exogenous (HMDB: HMDB0034892)

Food

Food (HMDB: HMDB0034892)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0034892)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034892)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	202.00 to 203.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	652.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.538 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.39 g/L	ALOGPS
logP	2.14	ALOGPS
logP	1.47	ChemAxon
logS	-1.2	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	2	ChemAxon
Refractivity	44.79 m³·mol⁻¹	ChemAxon
Polarizability	17.12 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]+	132.33	31661259
DarkChem	[M-H]-	131.578	31661259
DeepCCS	[M+H]+	137.468	30932474
DeepCCS	[M-H]-	134.869	30932474
DeepCCS	[M-2H]-	171.343	30932474
DeepCCS	[M+Na]+	146.516	30932474
AllCCS	[M+H]+	130.8	32859911
AllCCS	[M+H-H2O]+	126.2	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.3	32859911
AllCCS	[M-H]-	132.9	32859911
AllCCS	[M+Na-2H]-	134.3	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.73 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3086 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	962.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	350.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	130.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	197.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	316.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	288.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	846.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	151.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1132.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	214.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	430.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	407.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	70.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-5-methyl-2-vinylpyrazine	CCC1=NC(C)=CN=C1C=C	1569.8	Standard polar	33892256
3-Ethyl-5-methyl-2-vinylpyrazine	CCC1=NC(C)=CN=C1C=C	1127.1	Standard non polar	33892256
3-Ethyl-5-methyl-2-vinylpyrazine	CCC1=NC(C)=CN=C1C=C	1175.6	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-Ethyl-5-methyl-2-vinylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-4900000000-bceee447b24bba5d9147	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 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 - 3-Ethyl-5-methyl-2-vinylpyrazine 10V, Positive-QTOF	splash10-0002-0900000000-77eaa1f1e312658324d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 20V, Positive-QTOF	splash10-0002-1900000000-f8e7dbb07474fa32a681	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 40V, Positive-QTOF	splash10-0036-9200000000-a85af822dbcc7c08128e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-f414bc445832b9285141	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 20V, Negative-QTOF	splash10-0002-1900000000-41f333e18e330785e635	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 40V, Negative-QTOF	splash10-0159-7900000000-8ce982aede44541813e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 10V, Positive-QTOF	splash10-0002-0900000000-2ef1a63f0d174650da9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 20V, Positive-QTOF	splash10-0002-2900000000-a5dd75618aed27e74c3e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 40V, Positive-QTOF	splash10-054o-9100000000-a18ba443ad5ff2a48210	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-953db906b70b80dc1768	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 20V, Negative-QTOF	splash10-014j-1900000000-3492fbb5df1c0c739bc6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methyl-2-vinylpyrazine 40V, Negative-QTOF	splash10-014l-9800000000-b561e7e689198fd5cad8	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]+)	2023-02-04	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

FDB013468

KNApSAcK ID

Not Available

Chemspider ID

4936482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6431144

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1552591

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-Ethyl-5-methyl-2-vinylpyrazine (HMDB0034892)

MOL for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

3D MOL for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

3D SDF for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

3D-SDF for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

PDB for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

3D PDB for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

SMILES for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

INCHI for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

Structure for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

3D Structure for HMDB0034892 (3-Ethyl-5-methyl-2-vinylpyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra