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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:12:06 UTC
Update Date2021-10-13 08:21:44 UTC
HMDB IDHMDB0039673
Secondary Accession Numbers
  • HMDB39673
Metabolite Identification
Common Name4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one
Description4-Ethyl-2-hydroxy-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. 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 4-ethyl-2-hydroxy-3-methyl-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 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one.
Structure
Data?1563863418
Synonyms
ValueSource
2-Cyclopenten-1-one, 4-ethyl-2-hydroxy-3-methylHMDB
4-Ethyl-3-methyl-2-hydroxy-2-cyclopenten-1-oneHMDB
4-Ethyl-3-methyl-2-hydroxycyclopent-2-en-1-oneHMDB
Chemical FormulaC8H12O2
Average Molecular Weight140.1797
Monoisotopic Molecular Weight140.083729628
IUPAC Name4-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one
Traditional Name4-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one
CAS Registry Number71387-71-8
SMILES
CCC1CC(=O)C(O)=C1C
InChI Identifier
InChI=1S/C8H12O2/c1-3-6-4-7(9)8(10)5(6)2/h6,10H,3-4H2,1-2H3
InChI KeyFFJYTCCZZSZBGQ-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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point260.47 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1112 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.615 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.2 g/LALOGPS
logP10(0.72) g/LALOGPS
logP10(1.5) g/LChemAxon
logS10(-0.91) g/LALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.14 m³·mol⁻¹ChemAxon
Polarizability15.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-oneCCC1CC(=O)C(O)=C1C1844.6Standard polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-oneCCC1CC(=O)C(O)=C1C1140.4Standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-oneCCC1CC(=O)C(O)=C1C1170.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,1TMS,isomer #1CCC1CC(=O)C(O[Si](C)(C)C)=C1C1306.9Semi standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,1TMS,isomer #2CCC1C=C(O[Si](C)(C)C)C(O)=C1C1361.7Semi standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1CCC1C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1C1453.4Semi standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,2TMS,isomer #1CCC1C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1C1492.6Standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,1TBDMS,isomer #1CCC1CC(=O)C(O[Si](C)(C)C(C)(C)C)=C1C1541.2Semi standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,1TBDMS,isomer #2CCC1C=C(O[Si](C)(C)C(C)(C)C)C(O)=C1C1568.3Semi standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1CCC1C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C1896.1Semi standard non polar33892256
4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one,2TBDMS,isomer #1CCC1C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C1836.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-057i-9300000000-40394082e8fc329a955d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one GC-MS (1 TMS) - 70eV, Positivesplash10-02ka-9800000000-984637d38da0e75051c22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 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 - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 10V, Positive-QTOFsplash10-0006-1900000000-b82173495557861ec7d62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 20V, Positive-QTOFsplash10-014i-9300000000-ed99c39758bd73656c8b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 40V, Positive-QTOFsplash10-1000-9000000000-89bf8f3b94494b95b1142016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 10V, Negative-QTOFsplash10-000i-0900000000-03baea4228b3a88d04142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 20V, Negative-QTOFsplash10-000i-2900000000-968a2fa22f6c5212ee2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 40V, Negative-QTOFsplash10-0abc-9300000000-4b77bd07d594a1174c662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 10V, Positive-QTOFsplash10-006x-4900000000-ca179bafb3cce9f8d3232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 20V, Positive-QTOFsplash10-0a4i-9100000000-b5d33032237d3fcbbe4c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 40V, Positive-QTOFsplash10-0a4l-9000000000-849df1cfacb983a45a3e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 10V, Negative-QTOFsplash10-000i-0900000000-a5734f49b62679635a5a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 20V, Negative-QTOFsplash10-000i-4900000000-f9ec6c6f79069a61b2f62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one 40V, Negative-QTOFsplash10-0006-9100000000-4c385d0ad27c0b9967cc2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDFDB019302
KNApSAcK IDNot Available
Chemspider ID460795
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound528704
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1619111
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.. .