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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:16 UTC

Update Date

2023-02-21 17:19:32 UTC

HMDB ID

HMDB0030345

Secondary Accession Numbers

HMDB30345

Metabolite Identification

Common Name

6-Acetyl-1,2,3,4-tetrahydropyridine

Description

6-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(3,4,5,6-Tetrahydro-2-pyridinyl)ethanone	ChEBI
1-(1,2,3,4-Tetrahydro-2-pyridinyl)ethanone	HMDB
2-Acetyl-3,4,5,6-tetrahydropyridine	HMDB
2-Acetyl-D1-piperideine	HMDB
2-Acetyl-D2-piperideine	HMDB
Methyl 3,4,5,6-tetrahydro-2-pyridyl ketone, 8ci	HMDB

Chemical Formula

C₇H₁₁NO

Average Molecular Weight

125.1683

Monoisotopic Molecular Weight

125.084063979

IUPAC Name

1-(3,4,5,6-tetrahydropyridin-2-yl)ethan-1-one

Traditional Name

1-(3,4,5,6-tetrahydropyridin-2-yl)ethanone

CAS Registry Number

27300-27-2

SMILES

CC(=O)C1=NCCCC1

InChI Identifier

InChI=1S/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5H2,1H3

InChI Key

GNZWXNKZMHJXNU-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Tetrahydropyridines

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

tetrahydropyridine (CHEBI:59533 )

Ontology

Ingestion (HMDB: HMDB0030345)

Source

Endogenous

Endogenous (HMDB: HMDB0030345)

Plant

Poaceae (HMDB: HMDB0030345)

Exogenous

Food

Food (HMDB: HMDB0030345)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Dish

Tex-mex cuisine

Taco (FooDB: FOOD00708)

Exogenous (HMDB: HMDB0030345)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	200.00 to 203.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1391 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.508 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.82 g/L	ALOGPS
logP	0.82	ALOGPS
logP	1.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	18.43	ChemAxon
pKa (Strongest Basic)	3.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.43 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.99 m³·mol⁻¹	ChemAxon
Polarizability	13.91 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]+	127.243	31661259
DarkChem	[M-H]-	122.553	31661259
DeepCCS	[M+H]+	134.071	30932474
DeepCCS	[M-H]-	131.568	30932474
DeepCCS	[M-2H]-	167.393	30932474
DeepCCS	[M+Na]+	142.586	30932474
AllCCS	[M+H]+	124.8	32859911
AllCCS	[M+H-H2O]+	119.9	32859911
AllCCS	[M+NH4]+	129.3	32859911
AllCCS	[M+Na]+	130.6	32859911
AllCCS	[M-H]-	127.1	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	131.5	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.	2.21 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4882 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1290.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	381.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	160.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	415.2 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	477.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	940.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	301.8 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	1054.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	232.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	476.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	347.7 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	79.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Acetyl-1,2,3,4-tetrahydropyridine	CC(=O)C1=NCCCC1	1562.8	Standard polar	33892256
6-Acetyl-1,2,3,4-tetrahydropyridine	CC(=O)C1=NCCCC1	1061.3	Standard non polar	33892256
6-Acetyl-1,2,3,4-tetrahydropyridine	CC(=O)C1=NCCCC1	1066.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Acetyl-1,2,3,4-tetrahydropyridine,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1=NCCCC1	1293.0	Semi standard non polar	33892256
6-Acetyl-1,2,3,4-tetrahydropyridine,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1=NCCCC1	1210.5	Standard non polar	33892256
6-Acetyl-1,2,3,4-tetrahydropyridine,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=NCCCC1	1500.3	Semi standard non polar	33892256
6-Acetyl-1,2,3,4-tetrahydropyridine,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=NCCCC1	1413.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9000000000-826567f242939272bc78	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 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 - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Positive-QTOF	splash10-004i-1900000000-f2c3d6f0b94c2dc7ac2f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Positive-QTOF	splash10-0a6r-9800000000-8f699797c50b755b0eb3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Positive-QTOF	splash10-0pc0-9000000000-c2ba7818e5c4277a5c6c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Negative-QTOF	splash10-00di-0900000000-e79ba148a5c64b0b8b87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Negative-QTOF	splash10-00di-1900000000-94ffe14910ca0c82355b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Negative-QTOF	splash10-067i-9200000000-d95d77ba41056a56224f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Negative-QTOF	splash10-00di-0900000000-1565546da99951edb740	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Negative-QTOF	splash10-00e9-6900000000-67ca17fda4405490d669	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Negative-QTOF	splash10-0006-9000000000-ecbc8db567ba465b5070	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 10V, Positive-QTOF	splash10-004i-1900000000-e5f9b5deeb11abf06ebc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 20V, Positive-QTOF	splash10-001l-9200000000-851d65406bb8f52a2eca	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Acetyl-1,2,3,4-tetrahydropyridine 40V, Positive-QTOF	splash10-0006-9000000000-69b41add7ab473afe587	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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, 1000 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

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

Not Available

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

FDB002189

KNApSAcK ID

Not Available

Chemspider ID

453844

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

6-Acetyl-2,3,4,5-tetrahydropyridine

METLIN ID

Not Available

PubChem Compound

520300

PDB ID

Not Available

ChEBI ID

59533

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1551931

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 6-Acetyl-1,2,3,4-tetrahydropyridine (HMDB0030345)

MOL for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

3D MOL for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

3D SDF for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

3D-SDF for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

PDB for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

3D PDB for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

SMILES for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

INCHI for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

Structure for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

3D Structure for HMDB0030345 (6-Acetyl-1,2,3,4-tetrahydropyridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra