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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:06 UTC

Update Date

2023-02-21 17:19:23 UTC

HMDB ID

HMDB0030001

Secondary Accession Numbers

HMDB30001

Metabolite Identification

Common Name

2-Acetyl-3-methylpyrazine

Description

2-Acetyl-3-methylpyrazine, also known as 2-methyl-3-acetylpyrazine or pyrazine, 2-acetyl-3-methyl, belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. Based on a literature review very few articles have been published on 2-Acetyl-3-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
1-(3-Methyl-2-pyrazinyl)ethanone	HMDB
1-(3-Methylpyrazinyl)-ethanone	HMDB
1-(3-Methylpyrazinyl)ethan-1-one	HMDB
1-(3-Methylpyrazinyl)ethanone, 9ci	HMDB
1-[3-Methyl-2-pyrazinyl]-1-ethanone	HMDB
2-Methyl-3-acetylpyrazine	HMDB
3-Acetyl-2-methylpyrazine	HMDB
Methyl (3-methylpyrazinyl) ketone, 8ci	HMDB
Pyrazine, 2-acetyl-3-methyl	HMDB
Pyrazine, 3-acetyl-2-methyl	HMDB

Chemical Formula

C₇H₈N₂O

Average Molecular Weight

136.1512

Monoisotopic Molecular Weight

136.063662888

IUPAC Name

1-(3-methylpyrazin-2-yl)ethan-1-one

Traditional Name

1-(3-methylpyrazin-2-yl)ethanone

CAS Registry Number

23787-80-6

SMILES

CC(=O)C1=NC=CN=C1C

InChI Identifier

InChI=1S/C7H8N2O/c1-5-7(6(2)10)9-4-3-8-5/h3-4H,1-2H3

InChI Key

QUNOTZOHYZZWKQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyrazine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0030001)
Cytoplasm (HMDB: HMDB0030001)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030001)

Source

Endogenous

Endogenous (HMDB: HMDB0030001)

Plant

Poaceae (HMDB: HMDB0030001)

Animal

Animal (HMDB: HMDB0030001)

Exogenous

Food

Food (HMDB: HMDB0030001)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Exogenous (HMDB: HMDB0030001)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	265.00 to 266.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	62410 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.484 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	42.5 g/L	ALOGPS
logP	0.42	ALOGPS
logP	-0.39	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	0.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.37 m³·mol⁻¹	ChemAxon
Polarizability	13.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.865	31661259
DarkChem	[M-H]-	124.145	31661259
DeepCCS	[M+H]+	130.189	30932474
DeepCCS	[M-H]-	127.546	30932474
DeepCCS	[M-2H]-	163.658	30932474
DeepCCS	[M+Na]+	138.808	30932474
AllCCS	[M+H]+	127.5	32859911
AllCCS	[M+H-H2O]+	122.8	32859911
AllCCS	[M+NH4]+	131.9	32859911
AllCCS	[M+Na]+	133.2	32859911
AllCCS	[M-H]-	126.9	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	130.6	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.	2.05 minutes	32390414
Predicted by Siyang on May 30, 2022	8.1919 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	484.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	295.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	83.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.9 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	263.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	575.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	578.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	35.1 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	726.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	452.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	500.0 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	179.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetyl-3-methylpyrazine	CC(=O)C1=NC=CN=C1C	1517.1	Standard polar	33892256
2-Acetyl-3-methylpyrazine	CC(=O)C1=NC=CN=C1C	1060.0	Standard non polar	33892256
2-Acetyl-3-methylpyrazine	CC(=O)C1=NC=CN=C1C	1082.2	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-Acetyl-3-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-50f8bcb11511d60226d0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetyl-3-methylpyrazine 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-Acetyl-3-methylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-15a5648d07f9e3c6da2e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 20V, Positive-QTOF	splash10-00kr-0900000000-516087a5eb1b10a3e9b3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 40V, Positive-QTOF	splash10-014i-9300000000-069fa37bed9eda5bc497	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 10V, Negative-QTOF	splash10-000i-0900000000-b8f004ee8e16dd9ab1f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 20V, Negative-QTOF	splash10-000l-6900000000-3c2ea14d8cc057539f74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 40V, Negative-QTOF	splash10-0006-9100000000-11f0db6a3a8ad15138aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 10V, Negative-QTOF	splash10-000i-2900000000-ecadedaf8113f5c5bd01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 20V, Negative-QTOF	splash10-0006-9100000000-8f7960e8b44c93a703f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 40V, Negative-QTOF	splash10-01ox-9000000000-81e788544a25eb14ff3f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 10V, Positive-QTOF	splash10-000i-0900000000-cba05f6a48e6982528d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 20V, Positive-QTOF	splash10-014r-7900000000-d1e8127c4e1b89dc44d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3-methylpyrazine 40V, Positive-QTOF	splash10-014l-9000000000-8c9106d7a4f4e55d6f57	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB001290

KNApSAcK ID

C00054980

Chemspider ID

29762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

32093

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1001571

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-Acetyl-3-methylpyrazine (HMDB0030001)

MOL for HMDB0030001 (2-Acetyl-3-methylpyrazine)

3D MOL for HMDB0030001 (2-Acetyl-3-methylpyrazine)

3D SDF for HMDB0030001 (2-Acetyl-3-methylpyrazine)

3D-SDF for HMDB0030001 (2-Acetyl-3-methylpyrazine)

PDB for HMDB0030001 (2-Acetyl-3-methylpyrazine)

3D PDB for HMDB0030001 (2-Acetyl-3-methylpyrazine)

SMILES for HMDB0030001 (2-Acetyl-3-methylpyrazine)

INCHI for HMDB0030001 (2-Acetyl-3-methylpyrazine)

Structure for HMDB0030001 (2-Acetyl-3-methylpyrazine)

3D Structure for HMDB0030001 (2-Acetyl-3-methylpyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra