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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:11:28 UTC

Update Date

2023-02-21 17:27:04 UTC

HMDB ID

HMDB0039661

Secondary Accession Numbers

HMDB39661

Metabolite Identification

Common Name

2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one

Description

2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one has been detected, but not quantified in, a few different foods, such as alcoholic beverages, breakfast cereal, and cereals and cereal products. This could make 2,3,6,7-tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.659   3.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.786   4.608   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.454   5.092   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       1.310   6.073   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   11                                                       
CONECT    6    7    8                                                       
CONECT    7    1    6   10                                                  
CONECT    8    4    6    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    7    9   12                                                  
CONECT   11    5    9                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₃NO

Average Molecular Weight

163.2163

Monoisotopic Molecular Weight

163.099714043

IUPAC Name

7-methyl-1H,2H,3H,6H,7H,8H-cyclopenta[b]azepin-8-one

Traditional Name

7-methyl-1H,2H,3H,6H,7H-cyclopenta[b]azepin-8-one

CAS Registry Number

97826-67-0

SMILES

CC1CC2=C(NCCC=C2)C1=O

InChI Identifier

InChI=1S/C10H13NO/c1-7-6-8-4-2-3-5-11-9(8)10(7)12/h2,4,7,11H,3,5-6H2,1H3

InChI Key

ILPLRBRVDMHSCS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepines

Sub Class

Not Available

Direct Parent

Azepines

Alternative Parents

Substituents

Azepine
Ketone
Secondary aliphatic amine
Enamine
Secondary amine
Azacycle
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen 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: HMDB0039661)
Cytoplasm (HMDB: HMDB0039661)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039661)

Source

Exogenous

Food

Food (HMDB: HMDB0039661)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Poaceae (HMDB: HMDB0039661)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039661)

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	10010 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	8.01 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.16	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	4.02	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	50.58 m³·mol⁻¹	ChemAxon
Polarizability	18.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	136.897	31661259
DarkChem	[M-H]-	131.74	31661259
DeepCCS	[M+H]+	135.537	30932474
DeepCCS	[M-H]-	131.71	30932474
DeepCCS	[M-2H]-	168.897	30932474
DeepCCS	[M+Na]+	144.397	30932474
AllCCS	[M+H]+	134.6	32859911
AllCCS	[M+H-H2O]+	130.0	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	139.0	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one	CC1CC2=C(NCCC=C2)C1=O	2394.0	Standard polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one	CC1CC2=C(NCCC=C2)C1=O	1650.6	Standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one	CC1CC2=C(NCCC=C2)C1=O	1510.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C2=C(C=CCCN2)C1	1775.1	Semi standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C2=C(C=CCCN2)C1	1613.2	Standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TMS,isomer #2	CC1CC2=C(C1=O)N([Si](C)(C)C)CCC=C2	1728.8	Semi standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TMS,isomer #2	CC1CC2=C(C1=O)N([Si](C)(C)C)CCC=C2	1565.3	Standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C2=C(C=CCCN2[Si](C)(C)C)C1	1864.6	Semi standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C2=C(C=CCCN2[Si](C)(C)C)C1	1705.3	Standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C2=C(C=CCCN2)C1	1976.4	Semi standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C2=C(C=CCCN2)C1	1804.3	Standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TBDMS,isomer #2	CC1CC2=C(C1=O)N([Si](C)(C)C(C)(C)C)CCC=C2	1938.3	Semi standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,1TBDMS,isomer #2	CC1CC2=C(C1=O)N([Si](C)(C)C(C)(C)C)CCC=C2	1789.6	Standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C2=C(C=CCCN2[Si](C)(C)C(C)(C)C)C1	2241.6	Semi standard non polar	33892256
2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C2=C(C=CCCN2[Si](C)(C)C(C)(C)C)C1	2075.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-007c-3900000000-280e943870ca5676f542	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-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 - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 10V, Positive-QTOF	splash10-03di-0900000000-de8f97f2eea6d65e9eb5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 20V, Positive-QTOF	splash10-08fr-0900000000-f3f72e91d71e78fd27c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 40V, Positive-QTOF	splash10-0k96-9200000000-dde68febbe499820708f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 10V, Negative-QTOF	splash10-03di-0900000000-d093885eb9942f971661	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 20V, Negative-QTOF	splash10-03di-0900000000-2511ea7cd06042326e18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 40V, Negative-QTOF	splash10-0udl-9400000000-2135c5270a4ca3e86793	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 10V, Negative-QTOF	splash10-03di-0900000000-3ca20f46ca7f1e0c7378	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 20V, Negative-QTOF	splash10-03di-0900000000-07b42b563995d6b8c41f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 40V, Negative-QTOF	splash10-01pp-2900000000-783d8c286936b1021ff0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 10V, Positive-QTOF	splash10-03di-0900000000-11ab2b98f52d5780db4a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 20V, Positive-QTOF	splash10-03di-0900000000-e2e13d326688766c4db3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one 40V, Positive-QTOF	splash10-000x-6900000000-38a3acb9c6762aa3842d	2021-09-25	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+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

FDB019290

KNApSAcK ID

Not Available

Chemspider ID

35014849

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67117575

PDB ID

Not Available

ChEBI ID

173429

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1879191

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 2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one (HMDB0039661)

MOL for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

3D MOL for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

3D SDF for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

3D-SDF for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

PDB for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

3D PDB for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

SMILES for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

INCHI for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

Structure for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

3D Structure for HMDB0039661 (2,3,6,7-Tetrahydro-7-methylcyclopent[b]azepin-8(1H)-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra