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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:52:10 UTC
Update Date2023-02-21 17:28:10 UTC
HMDB IDHMDB0040338
Secondary Accession Numbers
  • HMDB40338
Metabolite Identification
Common Name3,5,5-Trimethyl-3-cyclohexen-1-one
Description3,5,5-Trimethyl-3-cyclohexen-1-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3,5,5-Trimethyl-3-cyclohexen-1-one has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and saffrons (Crocus sativus). This could make 3,5,5-trimethyl-3-cyclohexen-1-one 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-3-cyclohexen-1-one.
Structure
Data?1677000490
Synonyms
ValueSource
.beta-isophoroneHMDB
3,5,5-Trimethyl-3-cyclohexene-1-oneHMDB
3,5,5-Trimethylcyclohex-3-enoneHMDB
b-IsophoroneHMDB
b-PhoroneHMDB
beta -IsophoroneHMDB
beta -PhoroneHMDB
beta-IsophoroneHMDB
beta-PhoroneHMDB
Crocusatin eHMDB
Chemical FormulaC9H14O
Average Molecular Weight138.2069
Monoisotopic Molecular Weight138.10446507
IUPAC Name3,5,5-trimethylcyclohex-3-en-1-one
Traditional Name3,5,5-trimethylcyclohex-3-en-1-one
CAS Registry Number471-01-2
SMILES
CC1=CC(C)(C)CC(=O)C1
InChI Identifier
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h5H,4,6H2,1-3H3
InChI KeyLKOKKQDYMZUSCG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point189.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility873.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.180 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.57 g/LALOGPS
logP1.72ALOGPS
logP1.96ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)16.62ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.67 m³·mol⁻¹ChemAxon
Polarizability16.27 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]+131.14531661259
DarkChem[M-H]-126.85231661259
DeepCCS[M+H]+135.6930932474
DeepCCS[M-H]-132.12130932474
DeepCCS[M-2H]-169.430932474
DeepCCS[M+Na]+144.88430932474
AllCCS[M+H]+126.732859911
AllCCS[M+H-H2O]+122.132859911
AllCCS[M+NH4]+131.032859911
AllCCS[M+Na]+132.232859911
AllCCS[M-H]-130.032859911
AllCCS[M+Na-2H]-131.932859911
AllCCS[M+HCOO]-134.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,5,5-Trimethyl-3-cyclohexen-1-oneCC1=CC(C)(C)CC(=O)C11392.9Standard polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-oneCC1=CC(C)(C)CC(=O)C1994.7Standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-oneCC1=CC(C)(C)CC(=O)C11064.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #1CC1=CC(C)(C)CC(O[Si](C)(C)C)=C11268.6Semi standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #1CC1=CC(C)(C)CC(O[Si](C)(C)C)=C11241.6Standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #2CC1=CC(C)(C)C=C(O[Si](C)(C)C)C11203.8Semi standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TMS,isomer #2CC1=CC(C)(C)C=C(O[Si](C)(C)C)C11174.7Standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #1CC1=CC(C)(C)CC(O[Si](C)(C)C(C)(C)C)=C11470.4Semi standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #1CC1=CC(C)(C)CC(O[Si](C)(C)C(C)(C)C)=C11480.6Standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #2CC1=CC(C)(C)C=C(O[Si](C)(C)C(C)(C)C)C11424.1Semi standard non polar33892256
3,5,5-Trimethyl-3-cyclohexen-1-one,1TBDMS,isomer #2CC1=CC(C)(C)C=C(O[Si](C)(C)C(C)(C)C)C11407.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-9200000000-44cce750b46a7c0248bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-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 - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Positive-QTOFsplash10-000i-0900000000-ae6ee4405608e5f7a0c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Positive-QTOFsplash10-000i-5900000000-7e83a4ecb52be1c7aca02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Positive-QTOFsplash10-052k-9000000000-c4a885c2890f13a744032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Negative-QTOFsplash10-000i-0900000000-12e4fd56237f81a516de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Negative-QTOFsplash10-000i-0900000000-57e3939106050a782b1a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Negative-QTOFsplash10-000f-9600000000-89b45e9ad286053f27662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Negative-QTOFsplash10-000i-0900000000-928b413704490084a3032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Negative-QTOFsplash10-000i-1900000000-968397034843fdc6f07d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Negative-QTOFsplash10-00dl-8900000000-c704e2adee956737100d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 10V, Positive-QTOFsplash10-0080-9700000000-8542f13911062f7bc78f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 20V, Positive-QTOFsplash10-0a6r-9100000000-7c34a35ebd7a83d066ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-3-cyclohexen-1-one 40V, Positive-QTOFsplash10-057u-9000000000-5a30ebfc7a84d63439d22021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 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 IDFDB020063
KNApSAcK IDC00032863
Chemspider ID9704
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10108
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1506341
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.. .