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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:54:04 UTC

Update Date

2023-02-21 17:23:10 UTC

HMDB ID

HMDB0033156

Secondary Accession Numbers

HMDB33156

Metabolite Identification

Common Name

Methoxypyrazine

Description

Methoxypyrazine is found in animal foods. Methoxypyrazine is a flavouring agent. Methoxypyrazine is present in cooked beef and cocoa Methoxypyrazines are a class of chemical compounds that produce odors. The odors may be desirable, as in the case of certain wines, or undesirable, as in the case of the Asian Lady Beetle which produces isopropyl methoxy pyrazine (IPMP). They have also been identified as additives in cigarette manufacture. Detection thresholds are very low, typically near 2 parts per trillion (1 ng/L).

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-Methoxy-pyrazine	ChEMBL, HMDB
2-Methoxy-1,4-diazine	HMDB
2-Methoxypyrazine	HMDB
FEMA 3302	HMDB
Methoxy-pyrazine	HMDB

Chemical Formula

C₅H₆N₂O

Average Molecular Weight

110.1139

Monoisotopic Molecular Weight

110.048012824

IUPAC Name

2-methoxypyrazine

Traditional Name

2-methoxypyrazine

CAS Registry Number

3149-28-8

SMILES

COC1=CN=CC=N1

InChI Identifier

InChI=1S/C5H6N2O/c1-8-5-4-6-2-3-7-5/h2-4H,1H3

InChI Key

WKSXRWSOSLGSTN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Methoxypyrazines

Alternative Parents

Substituents

Methoxypyrazine
Alkyl aryl ether
Heteroaromatic compound
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033156)
Cytoplasm (HMDB: HMDB0033156)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033156)

Source

Exogenous

Exogenous (HMDB: HMDB0033156)

Food

Food (HMDB: HMDB0033156)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Endogenous

Plant

Theobroma cacao (HMDB: HMDB0033156)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033156)

Biological role

Nutrient (HMDB: HMDB0033156)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	60.00 to 61.00 °C. @ 29.00 mm Hg	The Good Scents Company Information System
Water Solubility	25870 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.73	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	353 g/L	ALOGPS
logP	0.59	ALOGPS
logP	-0.025	ChemAxon
logS	0.51	ALOGPS
pKa (Strongest Basic)	0.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.01 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.52 m³·mol⁻¹	ChemAxon
Polarizability	10.56 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]+	120.679	31661259
DarkChem	[M-H]-	118.759	31661259
DeepCCS	[M+H]+	124.676	30932474
DeepCCS	[M-H]-	121.876	30932474
DeepCCS	[M-2H]-	158.17	30932474
DeepCCS	[M+Na]+	132.928	30932474
AllCCS	[M+H]+	124.1	32859911
AllCCS	[M+H-H2O]+	119.2	32859911
AllCCS	[M+NH4]+	128.7	32859911
AllCCS	[M+Na]+	130.0	32859911
AllCCS	[M-H]-	121.0	32859911
AllCCS	[M+Na-2H]-	123.6	32859911
AllCCS	[M+HCOO]-	126.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methoxypyrazine	COC1=CN=CC=N1	1283.2	Standard polar	33892256
Methoxypyrazine	COC1=CN=CC=N1	867.7	Standard non polar	33892256
Methoxypyrazine	COC1=CN=CC=N1	938.1	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 - Methoxypyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-9400000000-f0d7b83cc2264eebf07c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methoxypyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methoxypyrazine 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 - Methoxypyrazine 10V, Positive-QTOF	splash10-03di-1900000000-fda081551167973cfbaa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 20V, Positive-QTOF	splash10-03di-0900000000-590033940c7cc1a5d4d4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 40V, Positive-QTOF	splash10-0kai-9000000000-c1c5d52afd364d2b9fa6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 10V, Negative-QTOF	splash10-0a4i-1900000000-f0b30191136c63b9dcab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 20V, Negative-QTOF	splash10-0a4i-9000000000-dc05a18814c746076634	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 40V, Negative-QTOF	splash10-0a4i-9000000000-1b5a0b27beee51867795	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 10V, Positive-QTOF	splash10-03di-0900000000-93059203859099fa37d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 20V, Positive-QTOF	splash10-0il0-9700000000-cf5cdd5974711bf7bab3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 40V, Positive-QTOF	splash10-0udi-9000000000-61ba78950735fe2498bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 10V, Negative-QTOF	splash10-0a4i-0900000000-54009a42432c07b2ea86	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 20V, Negative-QTOF	splash10-0a4i-2900000000-5493f19dd566f14a0d53	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxypyrazine 40V, Negative-QTOF	splash10-0k96-9000000000-1debbc8e6d50fffa51ce	2021-09-25	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

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB011162

KNApSAcK ID

C00052644

Chemspider ID

17443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methoxypyrazines

METLIN ID

Not Available

PubChem Compound

18467

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Vallarino JG, Lopez-Cortes XA, Dunlevy JD, Boss PK, Gonzalez-Nilo FD, Moreno YM: Biosynthesis of methoxypyrazines: elucidating the structural/functional relationship of two Vitis viniferaO-methyltransferases capable of catalyzing the putative final step of the biosynthesis of 3-alkyl-2-methoxypyrazine. J Agric Food Chem. 2011 Jul 13;59(13):7310-6. doi: 10.1021/jf200542w. Epub 2011 Jun 9. [PubMed:21591781 ]
Kogel S, Eben A, Hoffmann C, Gross J: Influence of diet on fecundity, immune defense and content of 2-isopropyl-3-methoxypyrazine in Harmonia axyridis Pallas. J Chem Ecol. 2012 Jul;38(7):854-64. doi: 10.1007/s10886-012-0139-1. Epub 2012 May 31. [PubMed:22648506 ]
Sun Q, Gates MJ, Lavin EH, Acree TE, Sacks GL: Comparison of odor-active compounds in grapes and wines from vitis vinifera and non-foxy American grape species. J Agric Food Chem. 2011 Oct 12;59(19):10657-64. doi: 10.1021/jf2026204. Epub 2011 Sep 13. [PubMed:21879766 ]
van Leeuwen C, Roby JP, Alonso-Villaverde V, Gindro K: Impact of clonal variability in Vitis vinifera Cabernet franc on grape composition, wine quality, leaf blade stilbene content, and downy mildew resistance. J Agric Food Chem. 2013 Jan 9;61(1):19-24. doi: 10.1021/jf304687c. Epub 2012 Dec 14. [PubMed:23205623 ]
Suklje K, Lisjak K, Cesnik HB, Janes L, Du Toit W, Coetzee Z, Vanzo A, Deloire A: Classification of grape berries according to diameter and total soluble solids to study the effect of light and temperature on methoxypyrazine, glutathione, and hydroxycinnamate evolution during ripening of Sauvignon blanc (Vitis vinifera L.). J Agric Food Chem. 2012 Sep 19;60(37):9454-61. Epub 2012 Sep 10. [PubMed:22946638 ]
Kaneko S, Kumazawa K, Nishimura O: Studies on the key aroma compounds in soy milk made from three different soybean cultivars. J Agric Food Chem. 2011 Nov 23;59(22):12204-9. doi: 10.1021/jf202942h. Epub 2011 Oct 24. [PubMed:21981068 ]
Botezatu A, Pickering GJ: Determination of ortho- and retronasal detection thresholds and odor impact of 2,5-dimethyl-3-methoxypyrazine in wine. J Food Sci. 2012 Nov;77(11):S394-8. doi: 10.1111/j.1750-3841.2012.02942.x. Epub 2012 Oct 11. [PubMed:23057415 ]
Camara M, Gharbi N, Lenouvel A, Behr M, Guignard C, Orlewski P, Evers D: Detection and quantification of natural contaminants of wine by gas chromatography-differential ion mobility spectrometry (GC-DMS). J Agric Food Chem. 2013 Feb 6;61(5):1036-43. doi: 10.1021/jf303418q. Epub 2013 Jan 28. [PubMed:23356506 ]
Botezatu AI, Kotseridis Y, Inglis D, Pickering GJ: Occurrence and contribution of alkyl methoxypyrazines in wine tainted by Harmonia axyridis and Coccinella septempunctata. J Sci Food Agric. 2013 Mar 15;93(4):803-10. doi: 10.1002/jsfa.5800. Epub 2012 Oct 19. [PubMed:23079938 ]
Ma K, Zhang JN, Zhao M, He YJ: Accurate analysis of trace earthy-musty odorants in water by headspace solid phase microextraction gas chromatography-mass spectrometry. J Sep Sci. 2012 Jun;35(12):1494-501. doi: 10.1002/jssc.201200029. [PubMed:22740259 ]
Harris SA, Ryona I, Sacks GL: Behavior of 3-isobutyl-2-hydroxypyrazine (IBHP), a key intermediate in 3-isobutyl-2-methoxypyrazine (IBMP) metabolism, in ripening wine grapes. J Agric Food Chem. 2012 Dec 5;60(48):11901-8. doi: 10.1021/jf302990m. Epub 2012 Nov 26. [PubMed:23163527 ]
Bindon K, Varela C, Kennedy J, Holt H, Herderich M: Relationships between harvest time and wine composition in Vitis vinifera L. cv. Cabernet Sauvignon 1. Grape and wine chemistry. Food Chem. 2013 Jun 1;138(2-3):1696-705. doi: 10.1016/j.foodchem.2012.09.146. Epub 2012 Nov 10. [PubMed:23411300 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methoxypyrazine (HMDB0033156)

MOL for HMDB0033156 (Methoxypyrazine)

3D MOL for HMDB0033156 (Methoxypyrazine)

3D SDF for HMDB0033156 (Methoxypyrazine)

3D-SDF for HMDB0033156 (Methoxypyrazine)

PDB for HMDB0033156 (Methoxypyrazine)

3D PDB for HMDB0033156 (Methoxypyrazine)

SMILES for HMDB0033156 (Methoxypyrazine)

INCHI for HMDB0033156 (Methoxypyrazine)

Structure for HMDB0033156 (Methoxypyrazine)

3D Structure for HMDB0033156 (Methoxypyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra