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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:52:16 UTC

Update Date

2023-02-21 17:28:11 UTC

HMDB ID

HMDB0040340

Secondary Accession Numbers

HMDB40340

Metabolite Identification

Common Name

2-Isopropyl-3-methoxypyrazine

Description

2-Isopropyl-3-methoxypyrazine belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring. 2-Isopropyl-3-methoxypyrazine is a beany, earthy, and pea tasting compound. 2-Isopropyl-3-methoxypyrazine has been detected, but not quantified in, several different foods, such as orange bell peppers (Capsicum annuum), red bell peppers (Capsicum annuum), green bell peppers (Capsicum annuum), peppers (Capsicum annuum), and fishes. This could make 2-isopropyl-3-methoxypyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Isopropyl-3-methoxypyrazine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Isopropyl-2-methoxypyrazine	HMDB, MeSH
2-Methoxy-3-isopropylpyrazine	MeSH, HMDB
2-Isopropyl-3-methoxypyrazine	MeSH

Chemical Formula

C₈H₁₂N₂O

Average Molecular Weight

152.1937

Monoisotopic Molecular Weight

152.094963016

IUPAC Name

2-methoxy-3-(propan-2-yl)pyrazine

Traditional Name

2-methoxy-3-isopropylpyrazine

CAS Registry Number

25773-40-4

SMILES

COC1=NC=CN=C1C(C)C

InChI Identifier

InChI=1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3

InChI Key

NTOPKICPEQUPPH-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: HMDB0040340)
Cytoplasm (HMDB: HMDB0040340)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040340)

Source

Exogenous

Food

Food (HMDB: HMDB0040340)

Fishes (FooDB: FOOD00865)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Endogenous

Plant

Plant (HMDB: HMDB0040340)

Animal

Animal (HMDB: HMDB0040340)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040340)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0040340)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040340)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	120.00 to 125.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	698.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.414 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	61.4 g/L	ALOGPS
logP	2.08	ALOGPS
logP	1.35	ChemAxon
logS	-0.39	ALOGPS
pKa (Strongest Basic)	0.88	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	2	ChemAxon
Refractivity	42.31 m³·mol⁻¹	ChemAxon
Polarizability	16.41 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]+	133.176	31661259
DarkChem	[M-H]-	132.196	31661259
DeepCCS	[M+H]+	139.244	30932474
DeepCCS	[M-H]-	136.476	30932474
DeepCCS	[M-2H]-	172.493	30932474
DeepCCS	[M+Na]+	148.031	30932474
AllCCS	[M+H]+	132.5	32859911
AllCCS	[M+H-H2O]+	128.1	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	136.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Isopropyl-3-methoxypyrazine	COC1=NC=CN=C1C(C)C	1413.1	Standard polar	33892256
2-Isopropyl-3-methoxypyrazine	COC1=NC=CN=C1C(C)C	1062.5	Standard non polar	33892256
2-Isopropyl-3-methoxypyrazine	COC1=NC=CN=C1C(C)C	1105.2	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-Isopropyl-3-methoxypyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f76-7900000000-89789da5da35572fa227	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isopropyl-3-methoxypyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-4900000000-ae2469645399d144339f	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-Isopropyl-3-methoxypyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-e285b25da921fef16959	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 20V, Positive-QTOF	splash10-0udi-1900000000-b268081ebc09e0f7feb9	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 40V, Positive-QTOF	splash10-00xu-9200000000-dc84efe47461b1bb60ff	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 10V, Negative-QTOF	splash10-0udi-1900000000-2f7ddba10a979f8d8d0b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 20V, Negative-QTOF	splash10-0pb9-6900000000-a08d8f5215393a4cfbc8	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 40V, Negative-QTOF	splash10-014i-9000000000-69143a25f87748df0151	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-69fb340fe88fc17a618f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 20V, Positive-QTOF	splash10-0udl-5900000000-b7d79c1eac40fd036eb4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 40V, Positive-QTOF	splash10-0zfr-9000000000-58f719671aa890294871	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 10V, Negative-QTOF	splash10-0udi-0900000000-4920948e818c9af84110	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 20V, Negative-QTOF	splash10-0fr2-2900000000-79d44e91e9e8abd735e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-3-methoxypyrazine 40V, Negative-QTOF	splash10-0aou-9300000000-a50b0677924bf49ae6d5	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

DB01760

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020065

KNApSAcK ID

Not Available

Chemspider ID

30649

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isopropyl methoxy pyrazine

METLIN ID

Not Available

PubChem Compound

33166

PDB ID

IPZ

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1107761

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-Isopropyl-3-methoxypyrazine (HMDB0040340)

MOL for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

3D MOL for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

3D SDF for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

3D-SDF for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

PDB for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

3D PDB for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

SMILES for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

INCHI for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

Structure for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

3D Structure for HMDB0040340 (2-Isopropyl-3-methoxypyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra