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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:45 UTC

Update Date

2023-02-21 17:22:48 UTC

HMDB ID

HMDB0032933

Secondary Accession Numbers

HMDB32933

Metabolite Identification

Common Name

2-Methoxy-3-(1-methylpropyl)pyrazine

Description

2-Methoxy-3-(1-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-(1-methylpropyl)pyrazine is a bell, carrot, and earth tasting compound. 2-Methoxy-3-(1-methylpropyl)pyrazine has been detected, but not quantified in, several different foods, such as fenugreeks (Trigonella foenum-graecum), alcoholic beverages, root vegetables, orange bell peppers (Capsicum annuum), and pulses. This could make 2-methoxy-3-(1-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-(1-methylpropyl)pyrazine.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    7                                                            
CONECT    3   12                                                            
CONECT    4    1    7                                                       
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7    2    4    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   11   12                                                  
CONECT   10    5    8                                                       
CONECT   11    6    9                                                       
CONECT   12    3    9                                                       
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
2-Methoxy-3-(1-methyl-propyl) pyrazine	HMDB
2-Methoxy-3-(1-methylpropyl)-pyrazine	HMDB
2-Methoxy-3-sec-butylpyrazine	HMDB
2-Sec-butyl-3-methoxy-pyrazine	HMDB
2-Sec-butyl-3-methoxypyrazine	HMDB
2-Sec-butyl-3-methoxypyrazine, 8ci	HMDB
3-Sec-butyl-2-methoxypyrazine	HMDB
FEMA 3433	HMDB
Pyrazine, 2-methoxy, 3-sec-butyl	HMDB
Pyrazine, 3-methoxy-2-(1-methylpropyl)	HMDB

Chemical Formula

C₉H₁₄N₂O

Average Molecular Weight

166.2203

Monoisotopic Molecular Weight

166.11061308

IUPAC Name

2-(butan-2-yl)-3-methoxypyrazine

Traditional Name

2-methoxy-3-(sec-butyl)pyrazine

CAS Registry Number

24168-70-5

SMILES

CCC(C)C1=C(OC)N=CC=N1

InChI Identifier

InChI=1S/C9H14N2O/c1-4-7(2)8-9(12-3)11-6-5-10-8/h5-7H,4H2,1-3H3

InChI Key

QMQDJVIJVPEQHE-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: HMDB0032933)
Cytoplasm (HMDB: HMDB0032933)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032933)

Source

Exogenous

Exogenous (HMDB: HMDB0032933)

Food

Food (HMDB: HMDB0032933)

Common beet (FooDB: FOOD00025)
Green vegetables (FooDB: FOOD00872)

Herb and spice

Herb

Fenugreek (FooDB: FOOD00186)

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0032933)
Fabaceae (HMDB: HMDB0032933)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032933)

Biological role

Nutrient (HMDB: HMDB0032933)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	50.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	229.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.924 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.9 g/L	ALOGPS
logP	2.5	ALOGPS
logP	1.79	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Basic)	0.85	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	46.91 m³·mol⁻¹	ChemAxon
Polarizability	18.32 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]+	136.723	31661259
DarkChem	[M-H]-	135.715	31661259
DeepCCS	[M+H]+	138.017	30932474
DeepCCS	[M-H]-	134.187	30932474
DeepCCS	[M-2H]-	171.361	30932474
DeepCCS	[M+Na]+	147.013	30932474
AllCCS	[M+H]+	136.5	32859911
AllCCS	[M+H-H2O]+	132.2	32859911
AllCCS	[M+NH4]+	140.6	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	139.9	32859911
AllCCS	[M+HCOO]-	141.4	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.	3.0 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3323 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1883.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	522.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	204.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	349.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	551.2 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	628.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1298.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	320.5 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	1265.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	429.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	561.6 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	32.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-3-(1-methylpropyl)pyrazine	CCC(C)C1=C(OC)N=CC=N1	1480.2	Standard polar	33892256
2-Methoxy-3-(1-methylpropyl)pyrazine	CCC(C)C1=C(OC)N=CC=N1	1162.0	Standard non polar	33892256
2-Methoxy-3-(1-methylpropyl)pyrazine	CCC(C)C1=C(OC)N=CC=N1	1191.2	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-(1-methylpropyl)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ug3-8900000000-d59c6a45a3f59420ccff	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0079-4900000000-a56732b45eb5203cad2c	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-(1-methylpropyl)pyrazine 10V, Positive-QTOF	splash10-014i-0900000000-588fd221c9b82f2ca254	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 20V, Positive-QTOF	splash10-014i-0900000000-eb2eb7b0011b666a98f2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 40V, Positive-QTOF	splash10-0006-9000000000-47ae7eed3f45f15872b4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 10V, Negative-QTOF	splash10-014i-1900000000-12c585e05f3b97e2a828	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 20V, Negative-QTOF	splash10-0aor-5900000000-4826268dbad43e1b337e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 40V, Negative-QTOF	splash10-0059-9100000000-70f488276a3d77293eb4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 10V, Positive-QTOF	splash10-014i-0900000000-1ec7efe000cc5c76adc6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 20V, Positive-QTOF	splash10-014i-4900000000-490ccca717f62200a06e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 40V, Positive-QTOF	splash10-066r-9200000000-63fe40d2a764a4987302	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 10V, Negative-QTOF	splash10-014i-0900000000-c06e07ad75c433b516d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 20V, Negative-QTOF	splash10-066r-1900000000-5c938f56dd8a4c73cd79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-3-(1-methylpropyl)pyrazine 40V, Negative-QTOF	splash10-0a4i-9200000000-7a447dbfe785f322c052	2021-09-23	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

FDB010918

KNApSAcK ID

Not Available

Chemspider ID

453664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

520098

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1008681

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-(1-methylpropyl)pyrazine (HMDB0032933)

MOL for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

3D MOL for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

3D SDF for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

3D-SDF for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

PDB for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

3D PDB for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

SMILES for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

INCHI for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

Structure for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

3D Structure for HMDB0032933 (2-Methoxy-3-(1-methylpropyl)pyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra