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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:45:37 UTC

Update Date

2023-02-21 17:27:58 UTC

HMDB ID

HMDB0040223

Secondary Accession Numbers

HMDB40223

Metabolite Identification

Common Name

4-Acetyl-2-methylpyridine

Description

4-Acetyl-2-methylpyridine 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. 4-Acetyl-2-methylpyridine 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 4-acetyl-2-methylpyridine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Acetyl-2-methylpyridine.

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-(2-Methyl-4-pyridinyl)ethanone, 9ci	HMDB
4-Acetyl-2-picoline	HMDB
Methyl 2-methyl-4-pyridyl ketone, 8ci	HMDB

Chemical Formula

C₈H₉NO

Average Molecular Weight

135.1632

Monoisotopic Molecular Weight

135.068413915

IUPAC Name

1-(2-methylpyridin-4-yl)ethan-1-one

Traditional Name

1-(2-methylpyridin-4-yl)ethanone

CAS Registry Number

2732-28-7

SMILES

CC(=O)C1=CC(C)=NC=C1

InChI Identifier

InChI=1S/C8H9NO/c1-6-5-8(7(2)10)3-4-9-6/h3-5H,1-2H3

InChI Key

NIGBUKPEJHINOG-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
Methylpyridine
Pyridine
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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040223)
Cytoplasm (HMDB: HMDB0040223)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040223)

Source

Exogenous

Exogenous (HMDB: HMDB0040223)

Food

Food (HMDB: HMDB0040223)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0040223)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040223)

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	11510 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	66.7 g/L	ALOGPS
logP	1.02	ALOGPS
logP	0.44	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	15.85	ChemAxon
pKa (Strongest Basic)	3.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.9 m³·mol⁻¹	ChemAxon
Polarizability	14.58 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]+	129.684	31661259
DarkChem	[M-H]-	127.903	31661259
DeepCCS	[M+H]+	130.067	30932474
DeepCCS	[M-H]-	126.24	30932474
DeepCCS	[M-2H]-	163.856	30932474
DeepCCS	[M+Na]+	139.395	30932474
AllCCS	[M+H]+	126.0	32859911
AllCCS	[M+H-H2O]+	121.3	32859911
AllCCS	[M+NH4]+	130.5	32859911
AllCCS	[M+Na]+	131.8	32859911
AllCCS	[M-H]-	126.8	32859911
AllCCS	[M+Na-2H]-	128.5	32859911
AllCCS	[M+HCOO]-	130.5	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.	3.05 minutes	32390414
Predicted by Siyang on May 30, 2022	8.5892 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.75 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Acetyl-2-methylpyridine	CC(=O)C1=CC=NC(C)=C1	1809.7	Standard polar	33892256
4-Acetyl-2-methylpyridine	CC(=O)C1=CC=NC(C)=C1	1164.6	Standard non polar	33892256
4-Acetyl-2-methylpyridine	CC(=O)C1=CC=NC(C)=C1	1164.6	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 - 4-Acetyl-2-methylpyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-287443ad2a18de6bc291	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-2-methylpyridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-2-methylpyridine 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 - 4-Acetyl-2-methylpyridine 10V, Positive-QTOF	splash10-000i-0900000000-8e9212c6e979694e7fd4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 20V, Positive-QTOF	splash10-000i-2900000000-fe17476d9339b1c85432	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 40V, Positive-QTOF	splash10-0g06-9500000000-0ba5ba1a4711026ef99f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 10V, Negative-QTOF	splash10-001i-0900000000-4981b5307bd7d3682408	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 20V, Negative-QTOF	splash10-001i-1900000000-709573fe34e7e5bcf43b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 40V, Negative-QTOF	splash10-0006-9300000000-73f5663484ed7ad3c431	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 10V, Positive-QTOF	splash10-000l-6900000000-0961da38e4c9bec0bb09	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 20V, Positive-QTOF	splash10-000f-9800000000-31ba425c715b88508e80	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 40V, Positive-QTOF	splash10-00kf-9000000000-790e357d9152f02b3008	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 10V, Negative-QTOF	splash10-001l-4900000000-31c0e06d7732b9d09af6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 20V, Negative-QTOF	splash10-001l-5900000000-00475d36a75ba07e5534	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-2-methylpyridine 40V, Negative-QTOF	splash10-0006-9300000000-981c5aba8f3e731854ab	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)	2021-09-24	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

FDB019937

KNApSAcK ID

Not Available

Chemspider ID

13557772

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20705014

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1882331

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 4-Acetyl-2-methylpyridine (HMDB0040223)

MOL for HMDB0040223 (4-Acetyl-2-methylpyridine)

3D MOL for HMDB0040223 (4-Acetyl-2-methylpyridine)

3D SDF for HMDB0040223 (4-Acetyl-2-methylpyridine)

3D-SDF for HMDB0040223 (4-Acetyl-2-methylpyridine)

PDB for HMDB0040223 (4-Acetyl-2-methylpyridine)

3D PDB for HMDB0040223 (4-Acetyl-2-methylpyridine)

SMILES for HMDB0040223 (4-Acetyl-2-methylpyridine)

INCHI for HMDB0040223 (4-Acetyl-2-methylpyridine)

Structure for HMDB0040223 (4-Acetyl-2-methylpyridine)

3D Structure for HMDB0040223 (4-Acetyl-2-methylpyridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra