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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:50:34 UTC
Update Date2022-03-07 02:54:38 UTC
HMDB IDHMDB0035819
Secondary Accession Numbers
  • HMDB35819
Metabolite Identification
Common Name(-)-Isoborneol
Description(-)-Isoborneol 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 (-)-Isoborneol.
Structure
Data?1563905511
Synonyms
ValueSource
FEMA 2158HMDB
BorneolMeSH, HMDB
Isoborneol, (exo)-isomerMeSH, HMDB
Isoborneol, (1R-exo)-isomerMeSH, HMDB
Isoborneol, (endo)-isomerMeSH, HMDB
Isoborneol, (endo-(+-))-isomerMeSH, HMDB
Isoborneol, (1R-endo)-isomerMeSH, HMDB
IsoborneolMeSH, HMDB
(-)-(2R)-IsoborneolHMDB
(-)-Bornan-2-exo-olHMDB
(-)-IsoborneolHMDB
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-olHMDB
(R,R,R)-(-)-IsoborneolHMDB
2-exo-Bornyl alcoholHMDB
Isobornyl alcoholHMDB
exo-2-Hydroxy-1,7,7-trimethylnorbornaneHMDB
l-IsoborneolPhytoBank
(±)-IsoborneolPhytoBank
dl-IsoborneolPhytoBank
NSC 26350PhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
CAS Registry Number10334-13-1
SMILES
CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C2
InChI Identifier
InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
InChI KeyDTGKSKDOIYIVQL-MRTMQBJTSA-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
  • Bornane monoterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point212 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1186 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.8 g/LALOGPS
logP2.83ALOGPS
logP1.99ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.31 m³·mol⁻¹ChemAxon
Polarizability18.43 ųChemAxon
Number of Rings2ChemAxon
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]+136.031661259
DarkChem[M-H]-130.31431661259
DeepCCS[M+H]+142.79830932474
DeepCCS[M-H]-140.40230932474
DeepCCS[M-2H]-173.92930932474
DeepCCS[M+Na]+148.7130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-IsoborneolCC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C21662.7Standard polar33892256
(-)-IsoborneolCC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C21168.0Standard non polar33892256
(-)-IsoborneolCC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C21153.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Isoborneol,1TMS,isomer #1CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O[Si](C)(C)C)C21217.1Semi standard non polar33892256
(-)-Isoborneol,1TBDMS,isomer #1CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O[Si](C)(C)C(C)(C)C)C21477.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (-)-Isoborneol GC-EI-Q (Non-derivatized)splash10-0005-9200000000-66a44698625f85db99da2020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Isoborneol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bt9-1900000000-561b837a8b44dbfaea562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Isoborneol GC-MS (1 TMS) - 70eV, Positivesplash10-03k9-6930000000-42c843fe7b6dc6e988d92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Isoborneol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 1V, positive-QTOFsplash10-000i-1900000000-5ca1187f552ff564ef4c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 1V, positive-QTOFsplash10-000i-3900000000-4d9d1609f8db2aa452262020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 2V, positive-QTOFsplash10-000i-5900000000-96b6c2a93a81f990e5cd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 2V, positive-QTOFsplash10-000j-9800000000-e59940adf942eacbdd0e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 3V, positive-QTOFsplash10-001a-9500000000-c53784fc1bb63df575f02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 3V, positive-QTOFsplash10-0012-9300000000-7bb32334950aa43e174d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 4V, positive-QTOFsplash10-000t-9200000000-b624a408fde0b0b95fc32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 4V, positive-QTOFsplash10-000t-9000000000-dd98da52ad93c01d83a22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 6V, positive-QTOFsplash10-000t-9000000000-cfdbe937662b3a812a632020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 7V, positive-QTOFsplash10-00l2-9000000000-367cf23b451dbe8547462020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 9V, positive-QTOFsplash10-017i-9000000000-fe79ebe8bd77394af3a02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 10V, positive-QTOFsplash10-0693-9000000000-b08ed9d6f97e835191b92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol Orbitrap 13V, positive-QTOFsplash10-05r3-9000000000-d0231d31055bf6da8fc42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol n/a 10V, positive-QTOFsplash10-000t-9000000000-12d91b5ab3379725f8a32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol n/a 10V, positive-QTOFsplash10-014i-9000000000-fb41d95361a6747c13942020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Isoborneol n/a 10V, positive-QTOFsplash10-014i-9000000000-59ba5428676cdc8984e32020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 10V, Positive-QTOFsplash10-052r-0900000000-7eaa92cdc2cb1dd17c332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 20V, Positive-QTOFsplash10-052r-0900000000-fb1222abb6cef74eb0832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 40V, Positive-QTOFsplash10-00dr-2900000000-622438b8bd224a755c472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 10V, Negative-QTOFsplash10-0udi-0900000000-b64fc5b28acf2b8ce6ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 20V, Negative-QTOFsplash10-0udi-0900000000-404830ee9ef93bfec2b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 40V, Negative-QTOFsplash10-0fki-2900000000-5d8542e9c4643c74fa542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 10V, Positive-QTOFsplash10-08fr-4900000000-c5fb0f5b567a4f9fada92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 20V, Positive-QTOFsplash10-090r-9400000000-3329d0b3e6f71527a4bc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Isoborneol 40V, Positive-QTOFsplash10-0006-9000000000-1ab95ec8cd37ae806b102021-09-24Wishart 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 IDFDB014581
KNApSAcK IDC00011022
Chemspider ID4882019
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6321405
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1596291
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.