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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:23:45 UTC

Update Date

2023-02-21 17:25:39 UTC

HMDB ID

HMDB0037151

Secondary Accession Numbers

HMDB37151

Metabolite Identification

Common Name

2-Isopropyl-5-methylpyrazine

Description

2-Isopropyl-5-methylpyrazine belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. 2-Isopropyl-5-methylpyrazine is a coffee, earthy, and green tasting compound. 2-Isopropyl-5-methylpyrazine has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), potatos (Solanum tuberosum), root vegetables, cocoa and cocoa products, and fishes. This could make 2-isopropyl-5-methylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Isopropyl-5-methylpyrazine.

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-Isopropyl-5-methyl-pyrazine	HMDB
2-Methyl-5-(1-methylethyl)-pyrazine	HMDB
2-Methyl-5-(1-methylethyl)pyrazine	HMDB
2-Methyl-5-(1-methylethyl)pyrazine, 9ci	HMDB
2-Methyl-5-isopropylpyrazine	HMDB
5-Isopropyl-2-methylpyrazine	HMDB
FEMA 3554	HMDB

Chemical Formula

C₈H₁₂N₂

Average Molecular Weight

136.1943

Monoisotopic Molecular Weight

136.100048394

IUPAC Name

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

Traditional Name

2-isopropyl-5-methylpyrazine

CAS Registry Number

13925-05-8

SMILES

CC(C)C1=NC=C(C)N=C1

InChI Identifier

InChI=1S/C8H12N2/c1-6(2)8-5-9-7(3)4-10-8/h4-6H,1-3H3

InChI Key

PGTQKVQDZHXLOP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0037151)
Cytoplasm (HMDB: HMDB0037151)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037151)

Source

Exogenous

Exogenous (HMDB: HMDB0037151)

Food

Food (HMDB: HMDB0037151)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0037151)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037151)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	190.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1901 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.626 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	35.6 g/L	ALOGPS
logP	1.56	ALOGPS
logP	1.04	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Basic)	1.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.13 m³·mol⁻¹	ChemAxon
Polarizability	15.82 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]+	128.881	31661259
DarkChem	[M-H]-	129.392	31661259
DeepCCS	[M+H]+	136.808	30932474
DeepCCS	[M-H]-	132.981	30932474
DeepCCS	[M-2H]-	170.407	30932474
DeepCCS	[M+Na]+	145.883	30932474
AllCCS	[M+H]+	128.4	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	132.7	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	130.9	32859911
AllCCS	[M+Na-2H]-	132.8	32859911
AllCCS	[M+HCOO]-	134.9	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.	2.44 minutes	32390414
Predicted by Siyang on May 30, 2022	9.569 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.34 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	752.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	193.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	302.6 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	406.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	743.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	46.5 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	1052.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	253.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	348.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	354.7 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	67.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Isopropyl-5-methylpyrazine	CC(C)C1=NC=C(C)N=C1	1389.6	Standard polar	33892256
2-Isopropyl-5-methylpyrazine	CC(C)C1=NC=C(C)N=C1	1018.3	Standard non polar	33892256
2-Isopropyl-5-methylpyrazine	CC(C)C1=NC=C(C)N=C1	1075.4	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-Isopropyl-5-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9500000000-18ebb0a16ad0ad707afb	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isopropyl-5-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Isopropyl-5-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dr-2900000000-f2e19f2c14367832138b	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-5-methylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-677ec9793c964d77f846	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 20V, Positive-QTOF	splash10-000i-1900000000-da42aad742ec001821a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 40V, Positive-QTOF	splash10-06dl-9100000000-f5cc59a4921bc93140a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-a7d3dfafb276d73d0a72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 20V, Negative-QTOF	splash10-000i-1900000000-17b3ec6f184eac4fcbed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 40V, Negative-QTOF	splash10-014u-9300000000-7af2ac5135355945a1f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-560d709635c029cd0cba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 20V, Negative-QTOF	splash10-000i-4900000000-6405e04dc551d7b3f533	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 40V, Negative-QTOF	splash10-0fr6-9000000000-1c5a462e8a88a2f9eaee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-32a40ed1ef0f2d7ddbbf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 20V, Positive-QTOF	splash10-00ke-9100000000-4e89870f412830cd3c5b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Isopropyl-5-methylpyrazine 40V, Positive-QTOF	splash10-014m-9000000000-ac970e8b34a14c1ddf54	2021-09-23	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

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

FDB016146

KNApSAcK ID

Not Available

Chemspider ID

55603

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61700

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036821

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-methylpyrazine (HMDB0037151)

MOL for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

3D MOL for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

3D SDF for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

3D-SDF for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

PDB for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

3D PDB for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

SMILES for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

INCHI for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

Structure for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

3D Structure for HMDB0037151 (2-Isopropyl-5-methylpyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra