Showing Compound Card for 3-Acetylpyridine (CDB005469)

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Record Information
Version1.0
Created at2020-04-27 16:23:41 UTC
Updated at2021-01-04 20:37:44 UTC
CannabisDB IDCDB005469
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Acetylpyridine
Description3-Acetylpyridine, also known as beta-Acetylpyridine, 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. It is one of several isomers of acetylpyridine wherein the acetyl group is attached at different positions around the pyridine ring relative to the pyridinyl nitrogen. 3-Acetylpyridine exists as a viscous, colorless liquid that is moderately soluble in water. It has a sweet, nutty, popcorn or hawthorn aroma and a nutty, roasted, corn chip or corn-like taste and contributes to the flavor of corn tortillas, popcorn, and beer. 3-Acetylpyridine occurs naturally in a number of foods and beverages including beer, brandy, bread, coffee, roasted filberts and whiskey. 3-Acetylpyridine is one of 599 additives in cigarettes submitted to the United States Department of Health and Human Services in April 1994 (PMID: 17666709 ). 3-Acetylpyridine is a known neurotoxin preferentially targets the inferior olive (IO) neurons (the source of the climbing fiber inputs to the Purkinje cells of the cerebellum) and a consequent ataxia manifest by alterations in both balance and gait (PMID: 27986589 ). It is used as a metabolic antagonist in research to decrease levels of nicotinamide (niacinamide) in laboratory animals (PMID: 27986589 ). 3-Acetylpyridine is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Pyridin-3-yl-ethanoneMeSH
1-(3-Pyridenyl)ethanoneHMDB
1-(3-Pyridinyl)-ethanoneHMDB
1-(3-Pyridinyl)ethanoneHMDB
1-(3-Pyridinyl)ethanone, 9ciHMDB
1-Pyridin-3-ylethanoneHMDB
3-AcetopyridineHMDB
3-Acetyl-pyridineHMDB
3-Pyridyl methyl ketoneHMDB
beta -AcetylpyridineHMDB
beta-AcetylpyridineHMDB
C7H7NOHMDB
FEMA 3424HMDB
Ketone, methyl 3-pyridylHMDB
Methyl 3-pyridyl ketoneHMDB
Methyl beta -pyridyl ketoneHMDB
Methyl pyridyl ketoneHMDB
MP Silica TLCHMDB
PYRIDINE,3-acetylHMDB
3-AcetylpyridineMeSH
Chemical FormulaC7H7NO
Average Molecular Weight121.14
Monoisotopic Molecular Weight121.0528
IUPAC Name1-(pyridin-3-yl)ethan-1-one
Traditional Name3-acetylpyridine
CAS Registry Number350-03-8
SMILES
CC(=O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C7H7NO/c1-6(9)7-3-2-4-8-5-7/h2-5H,1H3
InChI KeyWEGYGNROSJDEIW-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl alkyl ketones
Alternative Parents
Substituents
  • Aryl alkyl ketone
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point13.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP0.43Not Available
Predicted Properties
PropertyValueSource
logP0.45ALOGPS
logP0.31ChemAxon
logS0.08ALOGPS
pKa (Strongest Acidic)15.55ChemAxon
pKa (Strongest Basic)3.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.96 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.3 m³·mol⁻¹ChemAxon
Polarizability12.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Acetylpyridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pkc-9600000000-df5d8042490bd3f644a1Spectrum
Predicted GC-MS3-Acetylpyridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-1c01003ae76a9001d0e42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-9a277652d37a9de4ee012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9400000000-f885609eeda51ccb3f362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-62499f33f4497856efa52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3900000000-90a6130557aaa07452ae2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-53243e78c498d89df7b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-9700000000-8bb174156fc0980cef3e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-8c012136c073bcee0a702021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-8163b483004d382d118c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6900000000-7e6168d2404ba05754c82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-801fa2364794501bc17e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-9000000000-525a18e21aee0999299a2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033131
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011132
KNApSAcK IDNot Available
Chemspider ID13856009
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Acetylpyridine
METLIN IDNot Available
PubChem Compound9589
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Rabinoff M, Caskey N, Rissling A, Park C: Pharmacological and chemical effects of cigarette additives. Am J Public Health. 2007 Nov;97(11):1981-91. doi: 10.2105/AJPH.2005.078014. Epub 2007 Jul 31. [PubMed:17666709 ]
  2. Wecker L, Marrero-Rosado B, Engberg ME, Johns BE, Philpot RM: 3-Acetylpyridine neurotoxicity in mice. Neurotoxicology. 2017 Jan;58:143-152. doi: 10.1016/j.neuro.2016.11.010. Epub 2016 Dec 13. [PubMed:27986589 ]