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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:16 UTC
Update Date2021-10-13 06:07:27 UTC
HMDB IDHMDB0030345
Secondary Accession Numbers
  • HMDB30345
Metabolite Identification
Common Name6-Acetyl-1,2,3,4-tetrahydropyridine
Description6-Acetyl-1,2,3,4-tetrahydropyridine is found in cereals and cereal products. Responsible for mousy taint in wines. 6-Acetyl-1,2,3,4-tetrahydropyridine is a constituent of wheat, popcorn and bread aroma 6-Acetyl-2,3,4,5-tetrahydropyridine is a substituted tetrahydropyridine and a cyclic imine as well as a ketone. The compound exists in a chemical equilibrium with its tautomer 6-acetyl-1,2,3,4-tetrahydropyridine that differs only by the position of the double bond in the tetrahydropyridine ring:; 6-Acetyl-2,3,4,5-tetrahydropyridine, with the IUPAC name 1-(3,4,5,6-tetrahydropyridin-2-yl)ethanone, is an aroma compound and flavor that gives baked goods such as white bread, pop corn, or tortillas their typical smell, together with its structural homolog 2-acetyl-1-pyrroline
Structure
Data?1563861972
Synonyms
ValueSource
1-(3,4,5,6-Tetrahydro-2-pyridinyl)ethanoneChEBI
1-(1,2,3,4-Tetrahydro-2-pyridinyl)ethanoneHMDB
2-Acetyl-3,4,5,6-tetrahydropyridineHMDB
2-Acetyl-D1-piperideineHMDB
2-Acetyl-D2-piperideineHMDB
Methyl 3,4,5,6-tetrahydro-2-pyridyl ketone, 8ciHMDB
Chemical FormulaC7H11NO
Average Molecular Weight125.1683
Monoisotopic Molecular Weight125.084063979
IUPAC Name1-(3,4,5,6-tetrahydropyridin-2-yl)ethan-1-one
Traditional Name1-(3,4,5,6-tetrahydropyridin-2-yl)ethanone
CAS Registry Number27300-27-2
SMILES
CC(=O)C1=NCCCC1
InChI Identifier
InChI=1S/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5H2,1H3
InChI KeyGNZWXNKZMHJXNU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentTetrahydropyridines
Alternative Parents
Substituents
  • Tetrahydropyridine
  • Ketimine
  • Ketone
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Imine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point200.00 to 203.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1391 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.508 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.82 g/LALOGPS
logP10(0.82) g/LALOGPS
logP10(1.3) g/LChemAxon
logS10(-1.8) g/LALOGPS
pKa (Strongest Acidic)18.43ChemAxon
pKa (Strongest Basic)3.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.99 m³·mol⁻¹ChemAxon
Polarizability13.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.24331661259
DarkChem[M-H]-122.55331661259
DeepCCS[M+H]+134.07130932474
DeepCCS[M-H]-131.56830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-Acetyl-1,2,3,4-tetrahydropyridineCC(=O)C1=NCCCC11562.8Standard polar33892256
6-Acetyl-1,2,3,4-tetrahydropyridineCC(=O)C1=NCCCC11061.3Standard non polar33892256
6-Acetyl-1,2,3,4-tetrahydropyridineCC(=O)C1=NCCCC11066.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Acetyl-1,2,3,4-tetrahydropyridine,1TMS,isomer #1C=C(O[Si](C)(C)C)C1=NCCCC11293.0Semi standard non polar33892256
6-Acetyl-1,2,3,4-tetrahydropyridine,1TMS,isomer #1C=C(O[Si](C)(C)C)C1=NCCCC11210.5Standard non polar33892256
6-Acetyl-1,2,3,4-tetrahydropyridine,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C1=NCCCC11500.3Semi standard non polar33892256
6-Acetyl-1,2,3,4-tetrahydropyridine,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C1=NCCCC11413.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9000000000-826567f242939272bc782017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Negative-QTOFsplash10-00di-0900000000-e79ba148a5c64b0b8b872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Negative-QTOFsplash10-00di-1900000000-94ffe14910ca0c82355b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Negative-QTOFsplash10-067i-9200000000-d95d77ba41056a56224f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Negative-QTOFsplash10-00di-0900000000-1565546da99951edb7402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Negative-QTOFsplash10-00e9-6900000000-67ca17fda4405490d6692021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Negative-QTOFsplash10-0006-9000000000-ecbc8db567ba465b50702021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Positive-QTOFsplash10-004i-1900000000-f2c3d6f0b94c2dc7ac2f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Positive-QTOFsplash10-0a6r-9800000000-8f699797c50b755b0eb32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Positive-QTOFsplash10-0pc0-9000000000-c2ba7818e5c4277a5c6c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Positive-QTOFsplash10-004i-1900000000-e5f9b5deeb11abf06ebc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Positive-QTOFsplash10-001l-9200000000-851d65406bb8f52a2eca2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Positive-QTOFsplash10-0006-9000000000-69b41add7ab473afe5872021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002189
KNApSAcK IDNot Available
Chemspider ID453844
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link6-Acetyl-2,3,4,5-tetrahydropyridine
METLIN IDNot Available
PubChem Compound520300
PDB IDNot Available
ChEBI ID59533
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1551931
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .