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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:35:52 UTC

Update Date

2023-02-21 17:27:31 UTC

HMDB ID

HMDB0040052

Secondary Accession Numbers

HMDB40052

Metabolite Identification

Common Name

2-Isopropyl-5-methoxypyrazine

Description

2-Isopropyl-5-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-5-methoxypyrazine has been detected, but not quantified in, several different foods, such as garden onions (Allium cepa), pulses, onion-family vegetables, fruits, and arabica coffees (Coffea arabica). This could make 2-isopropyl-5-methoxypyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Isopropyl-5-methoxypyrazine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₈H₁₂N₂O

Average Molecular Weight

152.1937

Monoisotopic Molecular Weight

152.094963016

IUPAC Name

2-methoxy-5-(propan-2-yl)pyrazine

Traditional Name

2-isopropyl-5-methoxypyrazine

CAS Registry Number

Not Available

SMILES

COC1=NC=C(N=C1)C(C)C

InChI Identifier

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

InChI Key

GSVQZEKWEURMLP-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

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040052)
Cytoplasm (HMDB: HMDB0040052)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040052)

Source

Exogenous

Exogenous (HMDB: HMDB0040052)

Food

Food (HMDB: HMDB0040052)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Brassica

Brassicas (FooDB: FOOD00857)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)

Herbs and Spices (FooDB: FOOD00866)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Pulse

Pulses (FooDB: FOOD00867)

Nut

Nuts (FooDB: FOOD00869)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Not Available

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040052)

Biological role

Nutrient (HMDB: HMDB0040052)

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	57.1 g/L	ALOGPS
logP	2.09	ALOGPS
logP	1.35	ChemAxon
logS	-0.43	ALOGPS
pKa (Strongest Basic)	0.54	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	16.64 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]+	134.357	31661259
DarkChem	[M-H]-	133.279	31661259
DeepCCS	[M+H]+	136.868	30932474
DeepCCS	[M-H]-	134.245	30932474
DeepCCS	[M-2H]-	170.132	30932474
DeepCCS	[M+Na]+	145.356	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.5	32859911
AllCCS	[M+NH4]+	137.1	32859911
AllCCS	[M+Na]+	138.2	32859911
AllCCS	[M-H]-	135.0	32859911
AllCCS	[M+Na-2H]-	136.6	32859911
AllCCS	[M+HCOO]-	138.4	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.	2.18 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7613 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.59 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1597.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	426.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	281.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	88.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	413.1 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	543.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1023.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	229.0 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	1082.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	405.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	474.0 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	44.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Isopropyl-5-methoxypyrazine	COC1=NC=C(N=C1)C(C)C	1422.6	Standard polar	33892256
2-Isopropyl-5-methoxypyrazine	COC1=NC=C(N=C1)C(C)C	1103.0	Standard non polar	33892256
2-Isopropyl-5-methoxypyrazine	COC1=NC=C(N=C1)C(C)C	1149.5	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 - 2-Isopropyl-5-methoxypyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f8i-7900000000-e4af4d8b5abadb7e4cb7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isopropyl-5-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 - 2-Isopropyl-5-methoxypyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-c8b6f779ee5eae32c6e3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 20V, Positive-QTOF	splash10-0udi-0900000000-65910022be85ae0182b8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 40V, Positive-QTOF	splash10-014i-9100000000-9ebe283cfa24e16b7270	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 10V, Negative-QTOF	splash10-0udi-1900000000-a4327b9226512f89b5d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 20V, Negative-QTOF	splash10-0a4i-9000000000-0ac29fea6cdf8d9ae3a6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 40V, Negative-QTOF	splash10-0a4i-9300000000-f636ceaf3646436d08d2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-4dca928c5defcd195898	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 20V, Positive-QTOF	splash10-0udi-4900000000-fd47f08ccb5faa5eb171	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 40V, Positive-QTOF	splash10-0kur-9000000000-b4b9a10b31112565c4d2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-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-5-methoxypyrazine 20V, Negative-QTOF	splash10-0udi-1900000000-f4182547e98e580fb167	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methoxypyrazine 40V, Negative-QTOF	splash10-0apl-9100000000-ea078a15cfbb2bc89326	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019739

KNApSAcK ID

Not Available

Chemspider ID

83563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92558

PDB ID

Not Available

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-Isopropyl-5-methoxypyrazine (HMDB0040052)

MOL for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

3D MOL for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

3D SDF for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

3D-SDF for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

PDB for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

3D PDB for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

SMILES for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

INCHI for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

Structure for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

3D Structure for HMDB0040052 (2-Isopropyl-5-methoxypyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra