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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 23:53:10 UTC
Update Date2021-09-23 23:53:10 UTC
HMDB IDHMDB0303163
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxy-3-methyl-2-cyclopenten-1-one
Description2-hydroxy-3-methyl-2-cyclopenten-1-one, also known as cyclotene, is a member of the class of compounds known as cyclic ketones. Cyclic ketones are organic compounds containing a ketone that is conjugated to a cyclic moiety. 2-hydroxy-3-methyl-2-cyclopenten-1-one is soluble (in water) and a very weakly acidic compound (based on its pKa). 2-hydroxy-3-methyl-2-cyclopenten-1-one is a caramel, maple, and maple syrup tasting compound and can be found in a number of food items such as pepper (c. annuum), green bell pepper, red bell pepper, and yellow bell pepper, which makes 2-hydroxy-3-methyl-2-cyclopenten-1-one a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
2-Hydroxy-1-methylcyclopenten-3-oneMeSH
CycloteneMeSH
Chemical FormulaC6H8O2
Average Molecular Weight112.1265
Monoisotopic Molecular Weight112.0524295
IUPAC Name2-hydroxy-3-methylcyclopent-2-en-1-one
Traditional Namecyclotene
CAS Registry NumberNot Available
SMILES
CC1=C(O)C(=O)CC1
InChI Identifier
InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3
InChI KeyCFAKWWQIUFSQFU-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
  • Enol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.19ALOGPS
logP0.77ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.99 m³·mol⁻¹ChemAxon
Polarizability11.5 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
AllCCS[M+H]+124.08432859911
AllCCS[M+H-H2O]+119.28832859911
AllCCS[M+Na]+129.85532859911
AllCCS[M+NH4]+128.56232859911
AllCCS[M-H]-121.7432859911
AllCCS[M+Na-2H]-124.36132859911
AllCCS[M+HCOO]-127.27532859911
DeepCCS[M+H]+125.21330932474
DeepCCS[M-H]-121.75630932474
DeepCCS[M-2H]-158.90130932474
DeepCCS[M+Na]+134.01830932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC11341.6Semi standard non polar33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC11394.5Standard non polar33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC11364.9Standard polar33892256
2-Hydroxy-3-methyl-2-cyclopenten-1-one,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
2-Hydroxy-3-methyl-2-cyclopenten-1-one,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
2-Hydroxy-3-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC11670.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-a5794263e8fc3b77a0da2016-09-22Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9300000000-bb5ced3db053bc297e392015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Positive-QTOFsplash10-03di-2900000000-443c9e416dd135f377f82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Positive-QTOFsplash10-03di-9600000000-ff69e503b03cae6a78002016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Positive-QTOFsplash10-0zfr-9000000000-3d372ea8b42cf1712eca2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Negative-QTOFsplash10-03di-0900000000-927a6165f31587a987472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Negative-QTOFsplash10-03di-3900000000-a9c6bddefe3fe4bc53962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Negative-QTOFsplash10-0f6x-9000000000-dc99abf78fed8af7f6dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Positive-QTOFsplash10-03di-9500000000-c5ab7a62fd90435027a32021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Positive-QTOFsplash10-014r-9000000000-ce380cfd591088691e0d2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Positive-QTOFsplash10-0006-9000000000-70fec2d9bc8407f4526d2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 10V, Negative-QTOFsplash10-01q9-9600000000-ef24c7460c2dd9567fd52021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 20V, Negative-QTOFsplash10-03di-9600000000-453c8a59b6989e49e6222021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-methyl-2-cyclopenten-1-one 40V, Negative-QTOFsplash10-0006-9000000000-f374341928e04208d34d2021-10-21Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart 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 IDFDB008103
KNApSAcK IDNot Available
Chemspider ID6408
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ReferencesNot Available