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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:57 UTC
Update Date2022-03-07 02:53:08 UTC
HMDB IDHMDB0031851
Secondary Accession Numbers
  • HMDB31851
Metabolite Identification
Common Name3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol
Description3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a significant number of articles have been published on 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol.
Structure
Data?1563862180
Synonyms
ValueSource
(5,5,6-Trimethyl-2-norbornyl)-cyclohexanolHMDB
1-(5,5,6-Trimethyl-2-norbornyl)cyclohexanol, 8ciHMDB
3-(5,5,6-Trimethyl-2-norbornyl)cyclohexanolHMDB
3-(5,5,6-trimethylbicyclo(2.2.1)Hept-2-yl)-cyclohexanolHMDB
3-(5,5,6-trimethylbicyclo(2.2.1)Hept-2-yl)cyclohexan-1-olHMDB
3-IsocamphylcyclohexanolHMDB
3-[5,5,6-trimethylbicyclo[2.2.1]Hept-2-yl]cyclohexan-1-olHMDB
Isocamphyl cyclohexanol, mixed isomersHMDB
Chemical FormulaC16H28O
Average Molecular Weight236.3929
Monoisotopic Molecular Weight236.214015518
IUPAC Name3-{5,5,6-trimethylbicyclo[2.2.1]heptan-2-yl}cyclohexan-1-ol
Traditional Nameisobornyl cyclohexanol
CAS Registry Number3407-42-9
SMILES
CC1C2CC(CC2C2CCCC(O)C2)C1(C)C
InChI Identifier
InChI=1S/C16H28O/c1-10-14-8-12(16(10,2)3)9-15(14)11-5-4-6-13(17)7-11/h10-15,17H,4-9H2,1-3H3
InChI KeyBWVZAZPLUTUBKD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
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 Solubility0.0013 g/LALOGPS
logP4.47ALOGPS
logP3.71ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.31ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.24 m³·mol⁻¹ChemAxon
Polarizability29.5 ųChemAxon
Number of Rings3ChemAxon
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]+157.92431661259
DarkChem[M-H]-153.44431661259
DeepCCS[M+H]+159.15830932474
DeepCCS[M-H]-156.830932474
DeepCCS[M-2H]-190.10630932474
DeepCCS[M+Na]+165.25130932474
AllCCS[M+H]+159.132859911
AllCCS[M+H-H2O]+155.432859911
AllCCS[M+NH4]+162.532859911
AllCCS[M+Na]+163.432859911
AllCCS[M-H]-167.632859911
AllCCS[M+Na-2H]-168.032859911
AllCCS[M+HCOO]-168.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanolCC1C2CC(CC2C2CCCC(O)C2)C1(C)C2334.4Standard polar33892256
3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanolCC1C2CC(CC2C2CCCC(O)C2)C1(C)C1821.3Standard non polar33892256
3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanolCC1C2CC(CC2C2CCCC(O)C2)C1(C)C1842.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol,1TMS,isomer #1CC1C2CC(CC2C2CCCC(O[Si](C)(C)C)C2)C1(C)C1949.8Semi standard non polar33892256
3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol,1TBDMS,isomer #1CC1C2CC(CC2C2CCCC(O[Si](C)(C)C(C)(C)C)C2)C1(C)C2195.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0axu-1930000000-1d2d91958204436900582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol GC-MS (1 TMS) - 70eV, Positivesplash10-00bc-3970000000-78ecd07df83f3b3ee3b32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 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-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 10V, Positive-QTOFsplash10-014r-0190000000-54a24717857d6d3b50302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 20V, Positive-QTOFsplash10-014r-3970000000-6f20076b5d176b17ba2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 40V, Positive-QTOFsplash10-00mo-6900000000-ddd30d755cb5b32fd7c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 10V, Negative-QTOFsplash10-000i-0090000000-5652e55b2aa6d128df9a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 20V, Negative-QTOFsplash10-000i-0090000000-2cbaff19db9f2930ac962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 40V, Negative-QTOFsplash10-00kr-4890000000-eef2e327012a079e84432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 10V, Positive-QTOFsplash10-000i-3390000000-855d7e433c2554b1fc552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 20V, Positive-QTOFsplash10-000i-5960000000-5cadc7fdcbb3594b44c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 40V, Positive-QTOFsplash10-053r-9200000000-ad4203fbe0f11686adeb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 10V, Negative-QTOFsplash10-000i-0090000000-48ed6ce5150f09d5abc82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 20V, Negative-QTOFsplash10-000i-0090000000-48ed6ce5150f09d5abc82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(5,6,6-Trimethylbicyclo[2.2.1]hept-1-yl)cyclohexanol 40V, Negative-QTOFsplash10-014r-0090000000-3813c8a2d696ef83be052021-09-23Wishart 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 IDFDB008535
KNApSAcK IDNot Available
Chemspider ID93057
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound103005
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 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.