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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:58 UTC

Update Date

2023-02-21 17:20:47 UTC

HMDB ID

HMDB0031543

Secondary Accession Numbers

HMDB31543

Metabolite Identification

Common Name

3-Methyl-1,2-cyclopentanedione

Description

3-Methyl-1,2-cyclopentanedione 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-1,2-cyclopentanedione is a sweet, caramel, and coffee tasting compound. 3-Methyl-1,2-cyclopentanedione has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), breakfast cereal, cereals and cereal products, coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3-methyl-1,2-cyclopentanedione 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-1,2-cyclopentanedione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-5-methyl-2-cyclopenten-1-one	HMDB
Benzil-related compound, 45	HMDB
Corylone	HMDB
Cyclotene	HMDB
FEMA 2700	HMDB
Methylcyclopentenolone (diketo form)	HMDB
3-Methyl-1,2-cyclopentanedione	MeSH

Chemical Formula

C₆H₈O₂

Average Molecular Weight

112.1265

Monoisotopic Molecular Weight

112.0524295

IUPAC Name

3-methylcyclopentane-1,2-dione

Traditional Name

3-methylcyclopentane-1,2-dione

CAS Registry Number

765-70-8

SMILES

CC1CCC(=O)C1=O

InChI Identifier

InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h4H,2-3H2,1H3

InChI Key

OACYKCIZDVVNJL-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

Ingestion (HMDB: HMDB0031543)

Source

Endogenous

Endogenous (HMDB: HMDB0031543)

Plant

Coffea (HMDB: HMDB0031543)
Poaceae (HMDB: HMDB0031543)

Exogenous

Food

Food (HMDB: HMDB0031543)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031543)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106.5 - 107 °C	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	63.9 g/L	ALOGPS
logP	0.71	ALOGPS
logP	1.43	ChemAxon
logS	-0.24	ALOGPS
pKa (Strongest Acidic)	16.14	ChemAxon
pKa (Strongest Basic)	-8.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	28.97 m³·mol⁻¹	ChemAxon
Polarizability	11.3 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]+	123.646	31661259
DarkChem	[M-H]-	118.509	31661259
DeepCCS	[M+H]+	127.681	30932474
DeepCCS	[M-H]-	124.881	30932474
DeepCCS	[M-2H]-	161.319	30932474
DeepCCS	[M+Na]+	136.024	30932474
AllCCS	[M+H]+	123.6	32859911
AllCCS	[M+H-H2O]+	118.8	32859911
AllCCS	[M+NH4]+	128.1	32859911
AllCCS	[M+Na]+	129.4	32859911
AllCCS	[M-H]-	122.2	32859911
AllCCS	[M+Na-2H]-	124.8	32859911
AllCCS	[M+HCOO]-	127.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1,2-cyclopentanedione	CC1CCC(=O)C1=O	1694.1	Standard polar	33892256
3-Methyl-1,2-cyclopentanedione	CC1CCC(=O)C1=O	936.6	Standard non polar	33892256
3-Methyl-1,2-cyclopentanedione	CC1CCC(=O)C1=O	1028.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CC1	1185.0	Semi standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CC1	1144.0	Standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #2	CC1CC=C(O[Si](C)(C)C)C1=O	1189.5	Semi standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #2	CC1CC=C(O[Si](C)(C)C)C1=O	1104.9	Standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1341.6	Semi standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	1394.5	Standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1	1441.3	Semi standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1	1359.3	Standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O	1431.0	Semi standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #2	CC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O	1332.8	Standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1824.5	Semi standard non polar	33892256
3-Methyl-1,2-cyclopentanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	1701.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione EI-B (Non-derivatized)	splash10-090u-9100000000-c6c4c4dbdc254a0bd933	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione EI-B (Non-derivatized)	splash10-090u-9100000000-c6c4c4dbdc254a0bd933	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-8b72fd9087b3a4aa805c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione 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 - 3-Methyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-03di-3900000000-c337912e5b992e386707	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-03dr-9300000000-e2baeae061a629833218	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-0pdi-9000000000-9b5debdd9d51daa37516	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-03di-0900000000-76c963d528f0d204fb03	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-03di-2900000000-0ef53fe951a294ab5718	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-0zgv-9000000000-c66599080f8dec7b66f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 10V, Positive-QTOF	splash10-03di-9700000000-48f919bfefb025dac5bf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Positive-QTOF	splash10-0a4l-9000000000-1c6345d1013a8170ff5c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Positive-QTOF	splash10-052o-9000000000-0f90b14a2c64d2f5cdf2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 10V, Negative-QTOF	splash10-03di-2900000000-26c6f1d78ba66490aa54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Negative-QTOF	splash10-01q9-9300000000-b6ef91451abd3777ced8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Negative-QTOF	splash10-052f-9000000000-7df3308a995fe4bb67f0	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

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

FDB008153

KNApSAcK ID

Not Available

Chemspider ID

55153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16211403

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-1,2-cyclopentanedione (HMDB0031543)

MOL for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

3D MOL for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

3D SDF for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

3D-SDF for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

PDB for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

3D PDB for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

SMILES for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

INCHI for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

Structure for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

3D Structure for HMDB0031543 (3-Methyl-1,2-cyclopentanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra