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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:14:09 UTC

Update Date

2023-02-21 17:25:09 UTC

HMDB ID

HMDB0036174

Secondary Accession Numbers

HMDB36174

Metabolite Identification

Common Name

2-Methyl-3-(2-methylpropyl)pyrazine

Description

2-Methyl-3-(2-methylpropyl)pyrazine, also known as 2-isobutyl-3-methyl-pyrazine or 2-methyl-3-isobutylpyrazine, 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-Methyl-3-(2-methylpropyl)pyrazine is a green, herbal, and sugar tasting compound. 2-methyl-3-(2-methylpropyl)pyrazine has been detected, but not quantified, in a few different foods, such as coffee and coffee products, potato, and root vegetables.

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-Isobutyl-3-methyl-pyrazine	HMDB
2-Isobutyl-3-methylpyrazine	HMDB
2-Isobutyl-3-methylpyrazine, 8ci	HMDB
2-Methyl-3-(2-methylpropyl)-pyrazine	HMDB
2-Methyl-3-isobutylpyrazine	HMDB
3-Methyl-2-isobutyl pyrazine	HMDB
FEMA 3133	HMDB

Chemical Formula

C₉H₁₄N₂

Average Molecular Weight

150.2209

Monoisotopic Molecular Weight

150.115698458

IUPAC Name

2-methyl-3-(2-methylpropyl)pyrazine

Traditional Name

2-methyl-3-(2-methylpropyl)pyrazine

CAS Registry Number

13925-06-9

SMILES

CC(C)CC1=C(C)N=CC=N1

InChI Identifier

InChI=1S/C9H14N2/c1-7(2)6-9-8(3)10-4-5-11-9/h4-5,7H,6H2,1-3H3

InChI Key

ZHMIODDNZRIENW-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: HMDB0036174)
Cytoplasm (HMDB: HMDB0036174)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036174)

Source

Exogenous

Exogenous (HMDB: HMDB0036174)

Food

Food (HMDB: HMDB0036174)

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)

Endogenous

Plant

Plant (HMDB: HMDB0036174)
Coffea (HMDB: HMDB0036174)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036174)

Biological role

Nutrient (HMDB: HMDB0036174)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	199.00 to 201.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1604 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.96	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	2.04	ALOGPS
logP	1.23	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	1.48	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	2	ChemAxon
Refractivity	44.7 m³·mol⁻¹	ChemAxon
Polarizability	17.49 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]+	133.222	31661259
DarkChem	[M-H]-	131.262	31661259
DeepCCS	[M+H]+	137.036	30932474
DeepCCS	[M-H]-	133.206	30932474
DeepCCS	[M-2H]-	170.608	30932474
DeepCCS	[M+Na]+	146.143	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.9	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	139.0	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.	3.17 minutes	32390414
Predicted by Siyang on May 30, 2022	8.9976 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	149.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	518.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	110.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	317.3 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	287.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	544.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	650.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	60.6 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	826.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	362.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	486.5 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	144.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-3-(2-methylpropyl)pyrazine	CC(C)CC1=C(C)N=CC=N1	1469.3	Standard polar	33892256
2-Methyl-3-(2-methylpropyl)pyrazine	CC(C)CC1=C(C)N=CC=N1	1114.4	Standard non polar	33892256
2-Methyl-3-(2-methylpropyl)pyrazine	CC(C)CC1=C(C)N=CC=N1	1131.3	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-Methyl-3-(2-methylpropyl)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-6900000000-25f1e88d980c40ffa22c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-6900000000-c1caca54331b4a13b4b9	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-Methyl-3-(2-methylpropyl)pyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-c2c20d7c48c92588d9f4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 20V, Positive-QTOF	splash10-0udi-1900000000-1e7d8e8ee5a27d30515f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 40V, Positive-QTOF	splash10-0aou-9100000000-8f2c46e48eee61313e49	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 10V, Negative-QTOF	splash10-0002-0900000000-ef0dbf50ab3047824526	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 20V, Negative-QTOF	splash10-0002-0900000000-e4eab65d24c36b7d5b75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 40V, Negative-QTOF	splash10-000x-9400000000-25813b7e0c8524fc0323	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 10V, Negative-QTOF	splash10-0002-0900000000-50a674f3d9a955d9216b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 20V, Negative-QTOF	splash10-0002-1900000000-88743fab03116481a462	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 40V, Negative-QTOF	splash10-0006-9000000000-985f816284914496b754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 10V, Positive-QTOF	splash10-0zfr-1900000000-4ae0963f3e76b4d79ee5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 20V, Positive-QTOF	splash10-0a4j-7900000000-e7a06580ad7fd4523d68	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-3-(2-methylpropyl)pyrazine 40V, Positive-QTOF	splash10-066r-9200000000-184ce17a163a6a45f4a9	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

FDB015028

KNApSAcK ID

Not Available

Chemspider ID

24535

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26333

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013671

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-Methyl-3-(2-methylpropyl)pyrazine (HMDB0036174)

MOL for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

3D MOL for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

3D SDF for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

3D-SDF for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

PDB for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

3D PDB for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

SMILES for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

INCHI for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

Structure for HMDB0036174 (2-Methyl-3-(2-methylpropyl)pyrazine)

3D Structure for HMDB0036174 (2-Methyl-3-(2-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