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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:12:24 UTC

Update Date

2023-02-21 17:27:06 UTC

HMDB ID

HMDB0039679

Secondary Accession Numbers

HMDB39679

Metabolite Identification

Common Name

5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one

Description

5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-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       6.895   7.236   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.450  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.990  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.450   5.990   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.974   4.525   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.974   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.466   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.990   5.990   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.220   3.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.466   4.525   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.220   2.080   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       7.930   4.049   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   11                                                       
CONECT    7    3   11                                                       
CONECT    8    1    4   10                                                  
CONECT    9    5   10   11                                                  
CONECT   10    8    9   12                                                  
CONECT   11    6    7    9                                                  
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

COMPND    HMDB0039679
HETATM    1  C1  UNL     1      -3.772  -0.307  -0.639  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.559  -0.270   0.254  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.345   1.040   0.931  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.876   1.116   1.107  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.293   0.266   0.271  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.110   0.024   0.114  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.996   0.978  -0.504  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.387   0.349  -0.391  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.041  -1.120  -0.374  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.830  -1.163   0.531  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.299  -0.433  -0.513  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.177  -1.048  -1.594  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.668  -0.608  -0.088  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.575  -1.121  -1.394  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.934   0.617  -1.195  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.667  -1.054   1.048  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.790   1.051   1.946  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.734   1.902   0.353  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.318   1.758   1.806  1.00  0.00           H  
HETATM   20  H8  UNL     1       1.996   1.957   0.010  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.769   1.162  -1.573  1.00  0.00           H  
HETATM   22  H10 UNL     1       4.002   0.575  -1.283  1.00  0.00           H  
HETATM   23  H11 UNL     1       3.868   0.627   0.562  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.748  -1.440  -1.398  1.00  0.00           H  
HETATM   25  H13 UNL     1       3.865  -1.722   0.039  1.00  0.00           H  
HETATM   26  H14 UNL     1       2.159  -1.043   1.570  1.00  0.00           H  
HETATM   27  H15 UNL     1       1.238  -2.091   0.401  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   11   16
CONECT    3    4   17   18
CONECT    4    5    5   19
CONECT    5    6   11
CONECT    6    7   10
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   26   27
CONECT   11   12   12
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

5-methyl-2-(pyrrolidin-1-yl)cyclopent-2-en-1-one

Traditional Name

5-methyl-2-(pyrrolidin-1-yl)cyclopent-2-en-1-one

CAS Registry Number

4933-43-1

SMILES

CC1CC=C(N2CCCC2)C1=O

InChI Identifier

InChI=1S/C10H15NO/c1-8-4-5-9(10(8)12)11-6-2-3-7-11/h5,8H,2-4,6-7H2,1H3

InChI Key

OYIXGZDXSCZURQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Not Available

Direct Parent

Pyrrolidines

Alternative Parents

Substituents

Pyrrolidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Azacycle
Enamine
Carbonyl group
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039679)
Cytoplasm (HMDB: HMDB0039679)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039679)

Source

Exogenous

Food

Food (HMDB: HMDB0039679)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0039679)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039679)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	145 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.65	ChemAxon
logS	-0.06	ALOGPS
pKa (Strongest Basic)	5.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.55 m³·mol⁻¹	ChemAxon
Polarizability	19.02 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]+	136.377	31661259
DarkChem	[M-H]-	134.109	31661259
DeepCCS	[M+H]+	137.408	30932474
DeepCCS	[M-H]-	133.58	30932474
DeepCCS	[M-2H]-	170.781	30932474
DeepCCS	[M+Na]+	146.32	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	140.8	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.2	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one	CC1CC=C(N2CCCC2)C1=O	1910.8	Standard polar	33892256
5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one	CC1CC=C(N2CCCC2)C1=O	1444.4	Standard non polar	33892256
5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one	CC1CC=C(N2CCCC2)C1=O	1433.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(N2CCCC2)=CC1	1737.5	Semi standard non polar	33892256
5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(N2CCCC2)=CC1	1511.0	Standard non polar	33892256
5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(N2CCCC2)=CC1	1942.7	Semi standard non polar	33892256
5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(N2CCCC2)=CC1	1722.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-7900000000-668818fa7461c98163c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-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 - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-014i-0900000000-a77919f1aa6f6876c5d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-066s-2900000000-d951e5bdb720705c1577	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0a4l-9300000000-0f494ed4a05067c430d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-03di-0900000000-ea43866871ff737800fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-03di-4900000000-11897ac4c52b572b739e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-00di-9400000000-854c69175a4e79039cd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-03di-0900000000-5a67776f4d9f6897ce74	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-03di-2900000000-f8eb778db3545d2ea2f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-066u-9500000000-39844b052d5987c472f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-014i-0900000000-a8baa4b5218fe504eb78	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-014i-2900000000-8cd19e0157d6d27fc5b8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-00di-9300000000-0ea98f639d998ddc058d	2021-09-24	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+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

FDB019308

KNApSAcK ID

Not Available

Chemspider ID

8009771

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9834050

PDB ID

Not Available

ChEBI ID

173452

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one (HMDB0039679)

MOL for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

3D MOL for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

3D SDF for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

3D-SDF for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

PDB for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

3D PDB for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

SMILES for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

INCHI for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

Structure for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

3D Structure for HMDB0039679 (5-Methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra