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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:00 UTC

Update Date

2023-02-21 17:21:24 UTC

HMDB ID

HMDB0031860

Secondary Accession Numbers

HMDB31860

Metabolite Identification

Common Name

2-Methoxy-3-(2-methylpropyl)pyrazine

Description

2-Methoxy-3-(2-methylpropyl)pyrazine belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring. 2-Methoxy-3-(2-methylpropyl)pyrazine is a bell, earth, and galbanum tasting compound. 2-Methoxy-3-(2-methylpropyl)pyrazine has been detected, but not quantified in, several different foods, such as orange bell peppers (Capsicum annuum), yellow bell peppers (Capsicum annuum), common grapes (Vitis vinifera), red bell peppers (Capsicum annuum), and pepper (c. frutescens). This could make 2-methoxy-3-(2-methylpropyl)pyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methoxy-3-(2-methylpropyl)pyrazine.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PRZ                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.326   3.026   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.326   1.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.008   0.716   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -2.342   1.486   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.342   3.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.008   3.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.659   0.716   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.659  -0.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.993  -1.594   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.326  -1.594   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.008  -0.824   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.342  -1.594   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1DZK	HMDB
2-Isobutyl-3-methoxy-pyrazine	HMDB
2-Isobutyl-3-methoxypyrazine	HMDB
2-Isobutyl-3-methoxypyrazine, 8ci	HMDB
2-Methoxy-3-(2-methyl-propyl) pyrazine	HMDB
2-Methoxy-3-(2-methylpropyl)-pyrazine	HMDB
2-Methoxy-3-isobutylpyrazine	HMDB, MeSH
3-Isobutyl-2-methoxypyrazine	HMDB, MeSH
3-Methoxy-2-isobutylpyrazine	HMDB
FEMA 3132	HMDB
Galbazine	HMDB
IBMP	HMDB
PRZ	HMDB
Pyrazine, 2-(2-methylpropyl)-3-methoxy	HMDB
Pyrazine, 2-isobutyl-3-methoxy	HMDB
Pyrazine, 2-methoxy, 3-isobutyl	HMDB
Pyrazine, 3-methoxy-2-(2-methylpropyl)	HMDB

Chemical Formula

C₉H₁₄N₂O

Average Molecular Weight

166.2203

Monoisotopic Molecular Weight

166.11061308

IUPAC Name

2-methoxy-3-(2-methylpropyl)pyrazine

Traditional Name

2-isobutyl-3-methoxypyrazine

CAS Registry Number

24683-00-9

SMILES

COC1=NC=CN=C1CC(C)C

InChI Identifier

InChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3

InChI Key

UXFSPRAGHGMRSQ-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

Cellular substructure

Extracellular (HMDB: HMDB0031860)
Cytoplasm (HMDB: HMDB0031860)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031860)

Source

Exogenous

Exogenous (HMDB: HMDB0031860)

Food

Food (HMDB: HMDB0031860)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Fruit

Berry

Common grape (FooDB: FOOD00204)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Endogenous (HMDB: HMDB0031860)

Plant

Plant (HMDB: HMDB0031860)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0031860)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031860)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.9 g/L	ALOGPS
logP	2.11	ALOGPS
logP	1.54	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Basic)	0.98	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	3	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	18.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	135.558	31661259
DarkChem	[M-H]-	137.402	31661259
DeepCCS	[M+H]+	140.227	30932474
DeepCCS	[M-H]-	137.424	30932474
DeepCCS	[M-2H]-	173.595	30932474
DeepCCS	[M+Na]+	149.133	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	131.7	32859911
AllCCS	[M+NH4]+	140.0	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	138.3	32859911
AllCCS	[M+Na-2H]-	139.7	32859911
AllCCS	[M+HCOO]-	141.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-3-(2-methylpropyl)pyrazine	COC1=NC=CN=C1CC(C)C	1466.8	Standard polar	33892256
2-Methoxy-3-(2-methylpropyl)pyrazine	COC1=NC=CN=C1CC(C)C	1167.3	Standard non polar	33892256
2-Methoxy-3-(2-methylpropyl)pyrazine	COC1=NC=CN=C1CC(C)C	1181.4	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 - 2-Methoxy-3-(2-methylpropyl)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9800000000-b2a76f846c9e6cdec480	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9800000000-0379fe3fc6cfe11798f3	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 - 2-Methoxy-3-(2-methylpropyl)pyrazine 10V, Negative-QTOF	splash10-014i-0900000000-f195deae40b120d03a2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 20V, Negative-QTOF	splash10-0aor-7900000000-ce68c6d37c62fbafe643	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 40V, Negative-QTOF	splash10-0a59-9100000000-fdcbed3bfb97241ae911	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 10V, Negative-QTOF	splash10-014i-0900000000-f72a38590d903075c866	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 20V, Negative-QTOF	splash10-001i-2900000000-8a6a0e5c0c27143a34f1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 40V, Negative-QTOF	splash10-0a4i-9300000000-02b43dab5d60f685355e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 10V, Positive-QTOF	splash10-014i-0900000000-36e5a9d0812fa5b880dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 20V, Positive-QTOF	splash10-014i-1900000000-a3ae70c6cad1c5005bd3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 40V, Positive-QTOF	splash10-0006-9000000000-1252189c65cc284d2024	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 10V, Positive-QTOF	splash10-014i-0900000000-d120bc32d136e668f60a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 20V, Positive-QTOF	splash10-014i-2900000000-b41ddec9414daee33f17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(2-methylpropyl)pyrazine 40V, Positive-QTOF	splash10-014l-9100000000-4674a4a6a16f025751ab	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

DB04512

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008544

KNApSAcK ID

C00052644

Chemspider ID

30208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

32594

PDB ID

PRZ

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 2-Methoxy-3-(2-methylpropyl)pyrazine (HMDB0031860)

MOL for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

3D MOL for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

3D SDF for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

3D-SDF for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

PDB for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

3D PDB for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

SMILES for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

INCHI for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

Structure for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

3D Structure for HMDB0031860 (2-Methoxy-3-(2-methylpropyl)pyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra