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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:58 UTC
Update Date2023-02-21 17:20:47 UTC
HMDB IDHMDB0031543
Secondary Accession Numbers
  • HMDB31543
Metabolite Identification
Common Name3-Methyl-1,2-cyclopentanedione
Description3-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
Data?1677000047
Synonyms
ValueSource
2-Hydroxy-5-methyl-2-cyclopenten-1-oneHMDB
Benzil-related compound, 45HMDB
CoryloneHMDB
CycloteneHMDB
FEMA 2700HMDB
Methylcyclopentenolone (diketo form)HMDB
3-Methyl-1,2-cyclopentanedioneMeSH
Chemical FormulaC6H8O2
Average Molecular Weight112.1265
Monoisotopic Molecular Weight112.0524295
IUPAC Name3-methylcyclopentane-1,2-dione
Traditional Name3-methylcyclopentane-1,2-dione
CAS Registry Number765-70-8
SMILES
CC1CCC(=O)C1=O
InChI Identifier
InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h4H,2-3H2,1H3
InChI KeyOACYKCIZDVVNJL-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point106.5 - 107 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility63.9 g/LALOGPS
logP0.71ALOGPS
logP1.43ChemAxon
logS-0.24ALOGPS
pKa (Strongest Acidic)16.14ChemAxon
pKa (Strongest Basic)-8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.97 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.64631661259
DarkChem[M-H]-118.50931661259
DeepCCS[M+H]+127.68130932474
DeepCCS[M-H]-124.88130932474
DeepCCS[M-2H]-161.31930932474
DeepCCS[M+Na]+136.02430932474
AllCCS[M+H]+123.632859911
AllCCS[M+H-H2O]+118.832859911
AllCCS[M+NH4]+128.132859911
AllCCS[M+Na]+129.432859911
AllCCS[M-H]-122.232859911
AllCCS[M+Na-2H]-124.832859911
AllCCS[M+HCOO]-127.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methyl-1,2-cyclopentanedioneCC1CCC(=O)C1=O1694.1Standard polar33892256
3-Methyl-1,2-cyclopentanedioneCC1CCC(=O)C1=O936.6Standard non polar33892256
3-Methyl-1,2-cyclopentanedioneCC1CCC(=O)C1=O1028.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)CC11185.0Semi standard non polar33892256
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)CC11144.0Standard non polar33892256
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #2CC1CC=C(O[Si](C)(C)C)C1=O1189.5Semi standard non polar33892256
3-Methyl-1,2-cyclopentanedione,1TMS,isomer #2CC1CC=C(O[Si](C)(C)C)C1=O1104.9Standard non polar33892256
3-Methyl-1,2-cyclopentanedione,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC11341.6Semi standard non polar33892256
3-Methyl-1,2-cyclopentanedione,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC11394.5Standard non polar33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC11441.3Semi standard non polar33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC11359.3Standard non polar33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #2CC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O1431.0Semi standard non polar33892256
3-Methyl-1,2-cyclopentanedione,1TBDMS,isomer #2CC1CC=C(O[Si](C)(C)C(C)(C)C)C1=O1332.8Standard non polar33892256
3-Methyl-1,2-cyclopentanedione,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC11824.5Semi standard non polar33892256
3-Methyl-1,2-cyclopentanedione,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC11701.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione EI-B (Non-derivatized)splash10-090u-9100000000-c6c4c4dbdc254a0bd9332017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione EI-B (Non-derivatized)splash10-090u-9100000000-c6c4c4dbdc254a0bd9332018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9000000000-8b72fd9087b3a4aa805c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 10V, Positive-QTOFsplash10-03di-3900000000-c337912e5b992e3867072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Positive-QTOFsplash10-03dr-9300000000-e2baeae061a6298332182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Positive-QTOFsplash10-0pdi-9000000000-9b5debdd9d51daa375162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 10V, Negative-QTOFsplash10-03di-0900000000-76c963d528f0d204fb032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Negative-QTOFsplash10-03di-2900000000-0ef53fe951a294ab57182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Negative-QTOFsplash10-0zgv-9000000000-c66599080f8dec7b66f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 10V, Positive-QTOFsplash10-03di-9700000000-48f919bfefb025dac5bf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Positive-QTOFsplash10-0a4l-9000000000-1c6345d1013a8170ff5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Positive-QTOFsplash10-052o-9000000000-0f90b14a2c64d2f5cdf22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 10V, Negative-QTOFsplash10-03di-2900000000-26c6f1d78ba66490aa542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 20V, Negative-QTOFsplash10-01q9-9300000000-b6ef91451abd3777ced82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclopentanedione 40V, Negative-QTOFsplash10-052f-9000000000-7df3308a995fe4bb67f02021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008153
KNApSAcK IDNot Available
Chemspider ID55153
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16211403
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .