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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:59 UTC

Update Date

2023-02-21 17:20:47 UTC

HMDB ID

HMDB0031546

Secondary Accession Numbers

HMDB31546

Metabolite Identification

Common Name

3-Methyl-2-cyclopenten-1-one

Description

3-Methyl-2-cyclopenten-1-one belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. 3-Methyl-2-cyclopenten-1-one is a sweet, fatty, and fruity tasting compound. 3-Methyl-2-cyclopenten-1-one has been detected, but not quantified in, several different foods, such as green bell peppers (Capsicum annuum), orange bell peppers (Capsicum annuum), peppers (Capsicum annuum), red bell peppers (Capsicum annuum), and yellow bell peppers (Capsicum annuum). This could make 3-methyl-2-cyclopenten-1-one a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Methyl-2-cyclopenten-1-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-Methyl-1-cyclopenten-3-one	HMDB
3-Methyl-2-cyclopentenone	HMDB
3-Methylcyclopent-2-en-1-one	HMDB
3-Methylcyclopent-2-enone	HMDB
FEMA 3435	HMDB

Chemical Formula

C₆H₈O

Average Molecular Weight

96.1271

Monoisotopic Molecular Weight

96.057514878

IUPAC Name

3-methylcyclopent-2-en-1-one

Traditional Name

2-cyclopenten-1-one, 3-methyl-

CAS Registry Number

2758-18-1

SMILES

CC1=CC(=O)CC1

InChI Identifier

InChI=1S/C6H8O/c1-5-2-3-6(7)4-5/h4H,2-3H2,1H3

InChI Key

CHCCBPDEADMNCI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031546)
Cytoplasm (HMDB: HMDB0031546)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031546)

Source

Endogenous

Endogenous (HMDB: HMDB0031546)

Plant

Plant (HMDB: HMDB0031546)

Exogenous

Food

Food (HMDB: HMDB0031546)

Vegetable

Fruit vegetable

Exogenous (HMDB: HMDB0031546)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031546)

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	36.2 g/L	ALOGPS
logP	0.48	ALOGPS
logP	1.28	ChemAxon
logS	-0.42	ALOGPS
pKa (Strongest Acidic)	17.31	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	29.02 m³·mol⁻¹	ChemAxon
Polarizability	10.64 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]+	120.801	31661259
DarkChem	[M-H]-	113.917	31661259
DeepCCS	[M+H]+	124.454	30932474
DeepCCS	[M-H]-	121.639	30932474
DeepCCS	[M-2H]-	158.167	30932474
DeepCCS	[M+Na]+	133.029	30932474
AllCCS	[M+H]+	119.3	32859911
AllCCS	[M+H-H2O]+	114.3	32859911
AllCCS	[M+NH4]+	124.0	32859911
AllCCS	[M+Na]+	125.3	32859911
AllCCS	[M-H]-	120.5	32859911
AllCCS	[M+Na-2H]-	123.6	32859911
AllCCS	[M+HCOO]-	127.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-cyclopenten-1-one	CC1=CC(=O)CC1	1405.9	Standard polar	33892256
3-Methyl-2-cyclopenten-1-one	CC1=CC(=O)CC1	901.2	Standard non polar	33892256
3-Methyl-2-cyclopenten-1-one	CC1=CC(=O)CC1	937.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-2-cyclopenten-1-one,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC1	1132.4	Semi standard non polar	33892256
3-Methyl-2-cyclopenten-1-one,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC1	1055.5	Standard non polar	33892256
3-Methyl-2-cyclopenten-1-one,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC1	1368.9	Semi standard non polar	33892256
3-Methyl-2-cyclopenten-1-one,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC1	1253.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mn-9000000000-8bac1e9202c0570bd6a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-d631cc91da669ff9eac2	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-0002-9000000000-b817d322adc6668af7d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-0002-9000000000-775594f47ddc622ba4fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-016s-9000000000-24b0dbca6bb37e39bf18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 10V, Negative-QTOF	splash10-0002-9000000000-dc75a71cd84167e751db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 20V, Negative-QTOF	splash10-0002-9000000000-d3fe06b2963813ffc5f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 40V, Negative-QTOF	splash10-014i-9000000000-e0b178e1349fb3e26149	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-0002-9000000000-cf38049be2e4bea3276c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-0002-9000000000-adfe0ae0b64b16e3ad75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-0ufr-9000000000-d1105cf2e66ec0fd58a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 10V, Positive-QTOF	splash10-0002-9000000000-7f8b36253fb76331c2ea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 20V, Positive-QTOF	splash10-00ku-9000000000-30d62443464d26cb00ef	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-2-cyclopenten-1-one 40V, Positive-QTOF	splash10-004i-9000000000-b3de83013827feeaa8d2	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)	2021-09-16	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]+)	2023-02-04	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

FDB008156

KNApSAcK ID

Not Available

Chemspider ID

16723

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17691

PDB ID

Not Available

ChEBI ID

Not Available

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 3-Methyl-2-cyclopenten-1-one (HMDB0031546)

MOL for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

3D MOL for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

3D SDF for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

3D-SDF for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

PDB for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

3D PDB for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

SMILES for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

INCHI for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

Structure for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

3D Structure for HMDB0031546 (3-Methyl-2-cyclopenten-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra