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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:12:27 UTC
Update Date2022-03-07 02:56:18 UTC
HMDB IDHMDB0039680
Secondary Accession Numbers
  • HMDB39680
Metabolite Identification
Common Name3,5,5-Trimethyl-1,2-cyclopentanedione
Description3,5,5-Trimethyl-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. 3,5,5-Trimethyl-1,2-cyclopentanedione 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 3,5,5-trimethyl-1,2-cyclopentanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,5,5-Trimethyl-1,2-cyclopentanedione.
Structure
Data?1563863419
Synonyms
ValueSource
2-Hydroxy-3,5,5-trimethyl-2-cyclo-pentenoneHMDB
2-Hydroxy-3,5,5-trimethyl-2-cyclopenten-1-one, 9ciHMDB
Chemical FormulaC8H12O2
Average Molecular Weight140.1797
Monoisotopic Molecular Weight140.083729628
IUPAC Name3,3,5-trimethylcyclopentane-1,2-dione
Traditional Name3,3,5-trimethylcyclopentane-1,2-dione
CAS Registry Number53263-56-2
SMILES
CC1CC(C)(C)C(=O)C1=O
InChI Identifier
InChI=1S/C8H12O2/c1-5-4-8(2,3)7(10)6(5)9/h5H,4H2,1-3H3
InChI KeyGGXVKCBZJYLSCZ-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
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point87 - 88 °CNot Available
Boiling Point242.39 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1198 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.486 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.03 g/LALOGPS
logP1.38ALOGPS
logP2.53ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)16.57ChemAxon
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.04 m³·mol⁻¹ChemAxon
Polarizability15.05 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]+130.94631661259
DarkChem[M-H]-127.77831661259
DeepCCS[M+H]+131.65430932474
DeepCCS[M-H]-127.82330932474
DeepCCS[M-2H]-165.15830932474
DeepCCS[M+Na]+140.5230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,5,5-Trimethyl-1,2-cyclopentanedioneCC1CC(C)(C)C(=O)C1=O1682.1Standard polar33892256
3,5,5-Trimethyl-1,2-cyclopentanedioneCC1CC(C)(C)C(=O)C1=O1051.0Standard non polar33892256
3,5,5-Trimethyl-1,2-cyclopentanedioneCC1CC(C)(C)C(=O)C1=O1050.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,5,5-Trimethyl-1,2-cyclopentanedione,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)C(C)(C)C11249.3Semi standard non polar33892256
3,5,5-Trimethyl-1,2-cyclopentanedione,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)C(C)(C)C11177.8Standard non polar33892256
3,5,5-Trimethyl-1,2-cyclopentanedione,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)(C)C11476.8Semi standard non polar33892256
3,5,5-Trimethyl-1,2-cyclopentanedione,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)(C)C11393.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9200000000-61635fdee10363b297e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-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 - 3,5,5-Trimethyl-1,2-cyclopentanedione 10V, Positive-QTOFsplash10-0006-1900000000-6511d8d19bd8f13105712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 20V, Positive-QTOFsplash10-0006-9800000000-ace3258466b43558aa932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 40V, Positive-QTOFsplash10-05nf-9000000000-25009ac65af98f674bec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 10V, Negative-QTOFsplash10-000i-0900000000-c1316bcee802636f34452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 20V, Negative-QTOFsplash10-000i-1900000000-c30c1eb9d37514ce185b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 40V, Negative-QTOFsplash10-0awi-9400000000-7cd824e2e620c0cb32ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 10V, Positive-QTOFsplash10-000x-4900000000-84629fdaa73819ce9f3e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 20V, Positive-QTOFsplash10-059x-9200000000-9042624330b82b7869ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 40V, Positive-QTOFsplash10-0006-9000000000-733fa84191f55d58bb162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 10V, Negative-QTOFsplash10-000i-0900000000-a5734f49b62679635a5a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 20V, Negative-QTOFsplash10-01q0-5900000000-7dd1842f6987a542fadb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclopentanedione 40V, Negative-QTOFsplash10-059i-9800000000-e509b13d0833f90607dc2021-09-22Wishart 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
  • Membrane (predicted from logP)
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 IDFDB019309
KNApSAcK IDNot Available
Chemspider ID35014854
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69698813
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1619151
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.. .