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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:33:05 UTC

Update Date

2023-02-21 17:27:21 UTC

HMDB ID

HMDB0039999

Secondary Accession Numbers

HMDB39999

Metabolite Identification

Common Name

2-Acetyl-3,5-dimethylpyrazine

Description

2-Acetyl-3,5-dimethylpyrazine 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. 2-Acetyl-3,5-dimethylpyrazine is a caramel, hazelnut, and nutty tasting compound. 2-Acetyl-3,5-dimethylpyrazine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2-acetyl-3,5-dimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Acetyl-3,5-dimethylpyrazine.

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-(3,5-Dimethyl-2-pyrazinyl)-1-ethanone	HMDB
1-(3,5-Dimethyl-2-pyrazinyl)-ethanone	HMDB
1-(3,5-Dimethyl-2-pyrazinyl)ethanone	HMDB
1-(3,5-Dimethylpyrazinyl)-ethanone	HMDB
1-(3,5-Dimethylpyrazinyl)ethan-1-one	HMDB
1-(3,5-Dimethylpyrazinyl)ethanone, 9ci	HMDB
2-Acetyl-3,5(6)-dimethylpyrazine	HMDB
Pyrazine, 2-acetyl-3,5-dimethyl	HMDB

Chemical Formula

C₈H₁₀N₂O

Average Molecular Weight

150.1778

Monoisotopic Molecular Weight

150.079312952

IUPAC Name

1-(3,5-dimethylpyrazin-2-yl)ethan-1-one

Traditional Name

1-(3,5-dimethylpyrazin-2-yl)ethanone

CAS Registry Number

54300-08-2

SMILES

CC(=O)C1=C(C)N=C(C)C=N1

InChI Identifier

InChI=1S/C8H10N2O/c1-5-4-9-8(7(3)11)6(2)10-5/h4H,1-3H3

InChI Key

UCGOSAWBWFUKDT-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

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	70.00 °C. @ 7.00 mm Hg	The Good Scents Company Information System
Water Solubility	18550 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.139 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.3 g/L	ALOGPS
logP	0.82	ALOGPS
logP	-0.26	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	14.85	ChemAxon
pKa (Strongest Basic)	1.2	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	40.96 m³·mol⁻¹	ChemAxon
Polarizability	16.07 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]+	133.89	31661259
DarkChem	[M-H]-	131.208	31661259
DeepCCS	[M+H]+	134.67	30932474
DeepCCS	[M-H]-	131.199	30932474
DeepCCS	[M-2H]-	168.399	30932474
DeepCCS	[M+Na]+	143.938	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.1	32859911
AllCCS	[M+NH4]+	135.8	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	134.0	32859911
AllCCS	[M+HCOO]-	135.7	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.	2.73 minutes	32390414
Predicted by Siyang on May 30, 2022	8.6979 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.66 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	462.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	299.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.6 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	238.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	606.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	613.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	33.9 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	839.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	488.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	516.0 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	288.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetyl-3,5-dimethylpyrazine	CC(=O)C1=C(C)N=C(C)C=N1	1558.5	Standard polar	33892256
2-Acetyl-3,5-dimethylpyrazine	CC(=O)C1=C(C)N=C(C)C=N1	1144.2	Standard non polar	33892256
2-Acetyl-3,5-dimethylpyrazine	CC(=O)C1=C(C)N=C(C)C=N1	1157.4	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-Acetyl-3,5-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-6900000000-cac66b25398f62410a08	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 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-3,5-dimethylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-770f712e5e826c2cb5f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 20V, Positive-QTOF	splash10-0ue9-0900000000-bd35f79cd5aec49eb77a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 40V, Positive-QTOF	splash10-015c-9400000000-c0690f8a09ab4c0487f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-7fb0b85f4419fb6552e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 20V, Negative-QTOF	splash10-052b-0900000000-fa75afabd22785703de3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 40V, Negative-QTOF	splash10-0a5c-8900000000-1f72bc76f0a0a320bda5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-150ccace3c6c27ddc9f9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 20V, Positive-QTOF	splash10-001i-4900000000-05bc86e280892864bb33	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 40V, Positive-QTOF	splash10-00l6-9100000000-ee126ebfe463424b1783	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-d465dda09117a78fa7bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 20V, Negative-QTOF	splash10-0006-9700000000-f6dbd290136e93256f4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-3,5-dimethylpyrazine 40V, Negative-QTOF	splash10-07bf-9300000000-bc245a9708b9adf96374	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

FDB019681

KNApSAcK ID

Not Available

Chemspider ID

94540

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104721

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1594331

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-3,5-dimethylpyrazine (HMDB0039999)

MOL for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

3D MOL for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

3D SDF for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

3D-SDF for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

PDB for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

3D PDB for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

SMILES for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

INCHI for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

Structure for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

3D Structure for HMDB0039999 (2-Acetyl-3,5-dimethylpyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra