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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:14:10 UTC
Update Date2022-03-07 02:57:04 UTC
HMDB IDHMDB0041545
Secondary Accession Numbers
  • HMDB41545
Metabolite Identification
Common Name(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol
Description(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 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 small amount of articles have been published on (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol.
Structure
Data?1563863675
SynonymsNot Available
Chemical FormulaC10H18O3
Average Molecular Weight186.2481
Monoisotopic Molecular Weight186.125594442
IUPAC Name1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane-4,6-diol
Traditional Name1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane-4,6-diol
CAS Registry Number176896-61-0
SMILES
CC1(C)OC2(C)CCC1(O)CC2O
InChI Identifier
InChI=1S/C10H18O3/c1-8(2)10(12)5-4-9(3,13-8)7(11)6-10/h7,11-12H,4-6H2,1-3H3
InChI KeyPEWQMISWINPIPZ-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
  • P-menthane monoterpenoid
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point158 - 159 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility64.4 g/LALOGPS
logP0.6ALOGPS
logP0.12ChemAxon
logS-0.46ALOGPS
pKa (Strongest Acidic)13.42ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.63 m³·mol⁻¹ChemAxon
Polarizability20.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.39531661259
DarkChem[M-H]-136.27231661259
DeepCCS[M+H]+142.97530932474
DeepCCS[M-H]-139.14730932474
DeepCCS[M-2H]-176.5830932474
DeepCCS[M+Na]+152.11930932474
AllCCS[M+H]+141.332859911
AllCCS[M+H-H2O]+137.132859911
AllCCS[M+NH4]+145.232859911
AllCCS[M+Na]+146.332859911
AllCCS[M-H]-144.832859911
AllCCS[M+Na-2H]-145.632859911
AllCCS[M+HCOO]-146.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diolCC1(C)OC2(C)CCC1(O)CC2O2421.2Standard polar33892256
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diolCC1(C)OC2(C)CCC1(O)CC2O1392.2Standard non polar33892256
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diolCC1(C)OC2(C)CCC1(O)CC2O1380.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol,1TMS,isomer #1CC12CCC(O[Si](C)(C)C)(CC1O)C(C)(C)O21474.6Semi standard non polar33892256
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol,1TMS,isomer #2CC12CCC(O)(CC1O[Si](C)(C)C)C(C)(C)O21465.4Semi standard non polar33892256
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol,2TMS,isomer #1CC12CCC(O[Si](C)(C)C)(CC1O[Si](C)(C)C)C(C)(C)O21515.6Semi standard non polar33892256
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol,1TBDMS,isomer #1CC12CCC(O[Si](C)(C)C(C)(C)C)(CC1O)C(C)(C)O21727.5Semi standard non polar33892256
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol,1TBDMS,isomer #2CC12CCC(O)(CC1O[Si](C)(C)C(C)(C)C)C(C)(C)O21722.7Semi standard non polar33892256
(1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol,2TBDMS,isomer #1CC12CCC(O[Si](C)(C)C(C)(C)C)(CC1O[Si](C)(C)C(C)(C)C)C(C)(C)O21983.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01du-3900000000-bfbfd5550a1dcebc20d12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol GC-MS (2 TMS) - 70eV, Positivesplash10-06g3-9132000000-00a380dbd54bbd635fcf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 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 - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 10V, Positive-QTOFsplash10-000i-0900000000-6254f6744d63aca669152015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 20V, Positive-QTOFsplash10-00kr-0900000000-202bf80cf4af9641c4bf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 40V, Positive-QTOFsplash10-0uxr-0900000000-78d53d60271459fcde152015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 10V, Negative-QTOFsplash10-000i-0900000000-047a9c662f16cc2d226c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 20V, Negative-QTOFsplash10-000i-0900000000-d90aeb10ff0ff5dac0702015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 40V, Negative-QTOFsplash10-014i-0900000000-b645e5aff280bff7683c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 10V, Negative-QTOFsplash10-000i-0900000000-822190e00cd01cf01d8e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 20V, Negative-QTOFsplash10-000i-0900000000-822190e00cd01cf01d8e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 40V, Negative-QTOFsplash10-000i-0900000000-515722ea39f74cc1f81d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 10V, Positive-QTOFsplash10-000i-0900000000-b483467098b9f22137842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 20V, Positive-QTOFsplash10-000i-0900000000-7b606e4f71bbe89db9272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1R,2R,4R)-1,8-Epoxy-p-menthane-2,4-diol 40V, Positive-QTOFsplash10-000i-0900000000-aa166c5dd8f3a1f5c9442021-09-22Wishart 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
  • Cytoplasm
  • Extracellular
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 IDFDB021525
KNApSAcK IDNot Available
Chemspider ID163936
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound188642
PDB IDNot Available
ChEBI ID171973
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.