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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:20:33 UTC
Update Date2022-03-07 02:56:21 UTC
HMDB IDHMDB0039805
Secondary Accession Numbers
  • HMDB39805
Metabolite Identification
Common Name4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone
Description4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC13H24O2
Average Molecular Weight212.3285
Monoisotopic Molecular Weight212.177630012
IUPAC Name4-(3-hydroxybutyl)-3,3,5-trimethylcyclohexan-1-one
Traditional Name4-(3-hydroxybutyl)-3,3,5-trimethylcyclohexan-1-one
CAS Registry Number128660-70-8
SMILES
CC(O)CCC1C(C)CC(=O)CC1(C)C
InChI Identifier
InChI=1S/C13H24O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h9-10,12,14H,5-8H2,1-4H3
InChI KeyQIHMBTNCJUFMCE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.65ALOGPS
logP2.52ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)17.61ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.92 m³·mol⁻¹ChemAxon
Polarizability25.45 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.42231661259
DarkChem[M-H]-148.03131661259
DeepCCS[M+H]+156.5730932474
DeepCCS[M-H]-154.21230932474
DeepCCS[M-2H]-188.6230932474
DeepCCS[M+Na]+163.2230932474
AllCCS[M+H]+151.732859911
AllCCS[M+H-H2O]+147.932859911
AllCCS[M+NH4]+155.232859911
AllCCS[M+Na]+156.232859911
AllCCS[M-H]-156.732859911
AllCCS[M+Na-2H]-157.832859911
AllCCS[M+HCOO]-159.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanoneCC(O)CCC1C(C)CC(=O)CC1(C)C2417.6Standard polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanoneCC(O)CCC1C(C)CC(=O)CC1(C)C1564.2Standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanoneCC(O)CCC1C(C)CC(=O)CC1(C)C1637.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TMS,isomer #1CC(CCC1C(C)CC(=O)CC1(C)C)O[Si](C)(C)C1746.9Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TMS,isomer #2CC(O)CCC1C(C)CC(O[Si](C)(C)C)=CC1(C)C1764.6Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TMS,isomer #3CC(O)CCC1C(C)C=C(O[Si](C)(C)C)CC1(C)C1781.5Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #1CC(CCC1C(C)CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C1774.2Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #1CC(CCC1C(C)CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C1833.1Standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #2CC(CCC1C(C)C=C(O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C1794.7Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TMS,isomer #2CC(CCC1C(C)C=C(O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C1828.8Standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TBDMS,isomer #1CC(CCC1C(C)CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C1996.7Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TBDMS,isomer #2CC(O)CCC1C(C)CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C1992.9Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,1TBDMS,isomer #3CC(O)CCC1C(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)C2011.4Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #1CC(CCC1C(C)CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C2231.9Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #1CC(CCC1C(C)CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C2267.7Standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #2CC(CCC1C(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C2254.2Semi standard non polar33892256
4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone,2TBDMS,isomer #2CC(CCC1C(C)C=C(O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C2260.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ke-6900000000-1ed170c5f1f756ff297f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone GC-MS (1 TMS) - 70eV, Positivesplash10-00ri-9430000000-7d31754c4accaf7ad0e42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 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-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Positive-QTOFsplash10-0002-0920000000-d99ac261f26bfe1928ff2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Positive-QTOFsplash10-0002-3910000000-44347819cf2d3d8f4a6c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Positive-QTOFsplash10-0lxw-6900000000-7d683bd90b4689370e0a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Negative-QTOFsplash10-03di-0390000000-32de0f0c4a5d36cbd57a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Negative-QTOFsplash10-03dl-1890000000-d92ba42ef3e1cb4cf57b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Negative-QTOFsplash10-0k97-5900000000-eb495a9bcb06b23d1be82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Positive-QTOFsplash10-03fs-1930000000-6d95eb7a6fcc448a944c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Positive-QTOFsplash10-0a7i-6900000000-d00671822d95f97c0e1a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Positive-QTOFsplash10-0a4i-9500000000-0101eb1c6f0b6bb8863f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 10V, Negative-QTOFsplash10-03di-0290000000-766f2cf6532b8686b2eb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 20V, Negative-QTOFsplash10-03xr-0960000000-f7262a9568581bd427692021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3-Hydroxybutyl)-3,3,5-trimethylcyclohexanone 40V, Negative-QTOFsplash10-03xu-1910000000-6d9037c703ed9bcd1c7f2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB019455
KNApSAcK IDNot Available
Chemspider ID35014878
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752728
PDB IDNot Available
ChEBI ID168208
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.