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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:11:14 UTC

Update Date

2023-02-21 17:27:04 UTC

HMDB ID

HMDB0039657

Secondary Accession Numbers

HMDB39657

Metabolite Identification

Common Name

1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one

Description

1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 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. 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one has been detected, but not quantified in, alcoholic beverages. This could make 1,2,3,4,5,6-hexahydro-7H-cyclopenta[b]pyridin-7-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2,3,4,5,6-hexahydro-7H-1-Pyrindin-7-one, 12ci	HMDB

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.179

Monoisotopic Molecular Weight

137.084063979

IUPAC Name

1H,2H,3H,4H,5H,6H,7H-cyclopenta[b]pyridin-7-one

Traditional Name

1H,2H,3H,4H,5H,6H-cyclopenta[b]pyridin-7-one

CAS Registry Number

104704-30-5

SMILES

O=C1CCC2=C1NCCC2

InChI Identifier

InChI=1S/C8H11NO/c10-7-4-3-6-2-1-5-9-8(6)7/h9H,1-5H2

InChI Key

JOAMMKKZSZEDHD-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
Ketone
Secondary aliphatic amine
Enamine
Secondary amine
Azacycle
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039657)
Cytoplasm (HMDB: HMDB0039657)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039657)

Source

Exogenous

Food

Food (HMDB: HMDB0039657)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0039657)

Biological role

Nutrient (HMDB: HMDB0039657)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	68 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	50910 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	6.86 g/L	ALOGPS
logP	0.27	ALOGPS
logP	0.53	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	3.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.29 m³·mol⁻¹	ChemAxon
Polarizability	15.06 Å³	ChemAxon
Number of Rings	2	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]+	129.738	31661259
DarkChem	[M-H]-	125.101	31661259
DeepCCS	[M+H]+	134.386	30932474
DeepCCS	[M-H]-	132.117	30932474
DeepCCS	[M-2H]-	167.875	30932474
DeepCCS	[M+Na]+	142.583	30932474
AllCCS	[M+H]+	129.4	32859911
AllCCS	[M+H-H2O]+	124.7	32859911
AllCCS	[M+NH4]+	133.8	32859911
AllCCS	[M+Na]+	135.1	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	130.9	32859911
AllCCS	[M+HCOO]-	132.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one	O=C1CCC2=C1NCCC2	2304.4	Standard polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one	O=C1CCC2=C1NCCC2	1374.0	Standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one	O=C1CCC2=C1NCCC2	1381.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TMS,isomer #1	C[Si](C)(C)OC1=CCC2=C1NCCC2	1557.4	Semi standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TMS,isomer #1	C[Si](C)(C)OC1=CCC2=C1NCCC2	1510.9	Standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TMS,isomer #2	C[Si](C)(C)N1CCCC2=C1C(=O)CC2	1564.4	Semi standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TMS,isomer #2	C[Si](C)(C)N1CCCC2=C1C(=O)CC2	1468.2	Standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,2TMS,isomer #1	C[Si](C)(C)OC1=CCC2=C1N([Si](C)(C)C)CCC2	1686.8	Semi standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,2TMS,isomer #1	C[Si](C)(C)OC1=CCC2=C1N([Si](C)(C)C)CCC2	1623.6	Standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2=C1NCCC2	1778.8	Semi standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2=C1NCCC2	1660.7	Standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCC2=C1C(=O)CC2	1793.2	Semi standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCC2=C1C(=O)CC2	1730.3	Standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2=C1N([Si](C)(C)C(C)(C)C)CCC2	2105.0	Semi standard non polar	33892256
1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCC2=C1N([Si](C)(C)C(C)(C)C)CCC2	1978.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-8900000000-2cb9e2929561508486e7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 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 - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 10V, Positive-QTOF	splash10-000i-0900000000-3ab5fb89d4f90a8a697a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 20V, Positive-QTOF	splash10-000i-4900000000-04bf0cdbf17e09417879	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 40V, Positive-QTOF	splash10-0frx-9000000000-257699567f97bb4f1a97	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 10V, Negative-QTOF	splash10-000i-0900000000-cddec98f0121d4f902b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 20V, Negative-QTOF	splash10-000i-1900000000-fef159ed8f6d68f8cbcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 40V, Negative-QTOF	splash10-0pb9-9400000000-36f1d34ac3b3df8be4b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 10V, Negative-QTOF	splash10-000i-0900000000-fe28cc44ee8cb00ea1f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 20V, Negative-QTOF	splash10-000i-0900000000-4de2aa1d40b66c096e19	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 40V, Negative-QTOF	splash10-00rx-8900000000-e5df3f04e607b3c545c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 10V, Positive-QTOF	splash10-000i-0900000000-933a09a85a6fcb42d0db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 20V, Positive-QTOF	splash10-00dr-4900000000-5ed662a014932c997dc2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one 40V, Positive-QTOF	splash10-0006-9300000000-4cdce95cc41e8d84a8c8	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+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

FDB019286

KNApSAcK ID

Not Available

Chemspider ID

4934350

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6428973

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1879151

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 1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one (HMDB0039657)

MOL for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

3D MOL for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

3D SDF for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

3D-SDF for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

PDB for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

3D PDB for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

SMILES for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

INCHI for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

Structure for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

3D Structure for HMDB0039657 (1,2,3,4,5,6-Hexahydro-7H-cyclopenta[b]pyridin-7-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra