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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:00:15 UTC
Update Date2018-03-12 21:55:43 UTC
HMDB IDHMDB0036827
Secondary Accession Numbers
  • HMDB36827
Metabolite Identification
Common NameSclareol
DescriptionSclareol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Sclareol exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, sclareol is primarily located in the membrane (predicted from logP) and cytoplasm. Sclareol is a sweet, amber, and balsam tasting compound that can be found in a number of food items such as nutmeg, herbs and spices, common thyme, and tea. This makes sclareol a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
(13R)-Labd-14-ene-8,13-diolHMDB
Labd-14-ene-8,13-diolHMDB
Chemical FormulaC20H36O2
Average Molecular Weight308.4986
Monoisotopic Molecular Weight308.271530396
IUPAC Name1-(3-hydroxy-3-methylpent-4-en-1-yl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
Traditional Namesclareol
CAS Registry Number515-03-7
SMILES
CC(O)(CCC1C(C)(O)CCC2C(C)(C)CCCC12C)C=C
InChI Identifier
InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3
InChI KeyXVULBTBTFGYVRC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Labdane diterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point105.5 - 106 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP4.39ALOGPS
logP4.34ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)18.25ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.98 m³·mol⁻¹ChemAxon
Polarizability37.63 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-3290000000-f9ddd13ff0c9310704c7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-6302900000-625e7a58372c1b4541a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0092000000-2d33d9349017ace099c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-3190000000-de701adb29576c259657View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kur-9870000000-4b30f5fc6d71b9a7f341View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0092000000-2d33d9349017ace099c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-3190000000-de701adb29576c259657View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kur-9870000000-4b30f5fc6d71b9a7f341View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0049000000-f1667e5bf276e46930cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0096000000-64ed7fe3eed1d6617ae3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-5090000000-5625e7493ab215e16688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0049000000-f1667e5bf276e46930cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0096000000-64ed7fe3eed1d6617ae3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-5090000000-5625e7493ab215e16688View in MoNA
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
FoodDB IDFDB015776
KNApSAcK IDC00000894
Chemspider ID454751
KEGG Compound IDC09183
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521332
PDB IDNot Available
ChEBI ID9053
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hayet E, Fatma B, Souhir I, Waheb FA, Abderaouf K, Mahjoub A, Maha M: Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products. Pak J Pharm Sci. 2007 Apr;20(2):146-8. [PubMed:17416571 ]
  2. Patel NR, Hatziantoniou S, Georgopoulos A, Demetzos C, Torchilin VP, Weissig V, D'Souza GG: Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol. J Liposome Res. 2010 Sep;20(3):244-9. doi: 10.3109/08982100903347931. [PubMed:19883213 ]
  3. van den Brule S, Muller A, Fleming AJ, Smart CC: The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol. Plant J. 2002 Jun;30(6):649-62. [PubMed:12061897 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.