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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 19:49:18 UTC

Update Date

2023-02-21 17:24:28 UTC

HMDB ID

HMDB0034891

Secondary Accession Numbers

HMDB34891

Metabolite Identification

Common Name

3,5-Dimethyl-2-vinylpyrazine

Description

3,5-Dimethyl-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. 3,5-Dimethyl-2-vinylpyrazine is an earthy and musty tasting compound. 3,5-Dimethyl-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 3,5-dimethyl-2-vinylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,5-Dimethyl-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-3,5-dimethylpyrazine, 9ci	HMDB
Bis(2-nitrophenyl)sulfilimine	HMDB

Chemical Formula

C₈H₁₀N₂

Average Molecular Weight

134.1784

Monoisotopic Molecular Weight

134.08439833

IUPAC Name

2-ethenyl-3,5-dimethylpyrazine

Traditional Name

2-ethenyl-3,5-dimethylpyrazine

CAS Registry Number

157615-33-3

SMILES

CC1=CN=C(C=C)C(C)=N1

InChI Identifier

InChI=1S/C8H10N2/c1-4-8-7(3)10-6(2)5-9-8/h4-5H,1H2,2-3H3

InChI Key

ZUOLEJGELMNGPM-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: HMDB0034891)
Cytoplasm (HMDB: HMDB0034891)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034891)

Source

Exogenous

Food

Food (HMDB: HMDB0034891)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0034891)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034891)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	183.00 to 184.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1963 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.503 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.6 g/L	ALOGPS
logP	1.37	ALOGPS
logP	0.77	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Basic)	2.09	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	40.17 m³·mol⁻¹	ChemAxon
Polarizability	15.21 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]+	129.382	31661259
DarkChem	[M-H]-	126.694	31661259
DeepCCS	[M+H]+	130.022	30932474
DeepCCS	[M-H]-	126.195	30932474
DeepCCS	[M-2H]-	163.629	30932474
DeepCCS	[M+Na]+	139.168	30932474
AllCCS	[M+H]+	127.3	32859911
AllCCS	[M+H-H2O]+	122.6	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	132.9	32859911
AllCCS	[M-H]-	128.7	32859911
AllCCS	[M+Na-2H]-	130.5	32859911
AllCCS	[M+HCOO]-	132.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dimethyl-2-vinylpyrazine	CC1=CN=C(C=C)C(C)=N1	1524.0	Standard polar	33892256
3,5-Dimethyl-2-vinylpyrazine	CC1=CN=C(C=C)C(C)=N1	1055.6	Standard non polar	33892256
3,5-Dimethyl-2-vinylpyrazine	CC1=CN=C(C=C)C(C)=N1	1098.5	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-Dimethyl-2-vinylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-6900000000-32f277ee3814207367db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dimethyl-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 - 3,5-Dimethyl-2-vinylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-e4921cc32bf10e8b5145	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 20V, Positive-QTOF	splash10-000i-1900000000-eb1b99badba1d6b5baf3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 40V, Positive-QTOF	splash10-014l-9100000000-0b33c0302714ac4e0e74	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 10V, Negative-QTOF	splash10-001i-0900000000-865f3a49defceca8b822	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 20V, Negative-QTOF	splash10-001i-0900000000-474b92e4eded8611a1bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 40V, Negative-QTOF	splash10-066r-9700000000-022cd11d5de137a890fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 10V, Negative-QTOF	splash10-001i-0900000000-01d3d9050ab710b33e95	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 20V, Negative-QTOF	splash10-000x-9400000000-58d6ce13149d66273aab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 40V, Negative-QTOF	splash10-0296-9200000000-e69dc4e3911b2b30537b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-702022ba8dc6b16c2acb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 20V, Positive-QTOF	splash10-00kr-9700000000-5d7c43e8c3d341cbc01b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethyl-2-vinylpyrazine 40V, Positive-QTOF	splash10-014i-9000000000-b3d4c09897ec841ca505	2021-09-24	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

FDB013467

KNApSAcK ID

Not Available

Chemspider ID

4934645

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6429268

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1552571

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-Dimethyl-2-vinylpyrazine (HMDB0034891)

MOL for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

3D MOL for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

3D SDF for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

3D-SDF for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

PDB for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

3D PDB for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

SMILES for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

INCHI for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

Structure for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

3D Structure for HMDB0034891 (3,5-Dimethyl-2-vinylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra