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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:09:48 UTC
Update Date2019-07-23 06:18:03 UTC
HMDB IDHMDB0035213
Secondary Accession Numbers
  • HMDB35213
Metabolite Identification
Common Namebeta-Thujaplicin
Descriptionbeta-Thujaplicin, also known as hinokitiol or β-thujaplicin, belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. beta-Thujaplicin is an extremely weak basic (essentially neutral) compound (based on its pKa). beta-Thujaplicin is a phenolic and woody. Outside of the human body, beta-thujaplicin has been detected, but not quantified in, fruits. This could make beta-thujaplicin a potential biomarker for the consumption of these foods.
Structure
Data?1563862683
Synonyms
ValueSource
2-Hydroxy-4-isopropyl-cyclohepta2,4,6-trien-1-oneChEBI
4-IsopropyltropoloneChEBI
HinokitiolChEBI
b-ThujaplicinGenerator
Β-thujaplicinGenerator
2-Hydroxy-4(6)-(1-methylethyl)-2,4,6-cycloheptatrien-1-one, 9ciHMDB
2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropyl- 2,4,6-cycloheptatriene-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4, 6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-oneHMDB
4(6)-IsopropyltropoloneHMDB
4-Isopropyl-tropoloneHMDB
alpha-ThujaplicinHMDB
beta -IsopropyltropolonHMDB
beta -ThujaplicinHMDB
beta -ThujaplicineHMDB
beta-IsopropyltropolonHMDB
beta-IsopropyltropoloneHMDB
beta-ThujaplicineHMDB
Hinokitiol 4-isopropyltropoloneHMDB
HinokitolHMDB
IsopropyltropoloneHMDB
Thujaplicin, betaHMDB
beta-Thujaplicin, sodium saltHMDB
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
Traditional Namehinokitiol
CAS Registry Number499-44-5
SMILES
CC(C)C1=CC(=O)C(O)=CC=C1
InChI Identifier
InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
InChI KeyFUWUEFKEXZQKKA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.
KingdomOrganic compounds
Super ClassHydrocarbon derivatives
ClassTropones
Sub ClassTropolones
Direct ParentTropolones
Alternative Parents
Substituents
  • Tropolone
  • Cyclic ketone
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point52 - 52.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.2 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP1.8ALOGPS
logP2.06ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)11.44ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.55 m³·mol⁻¹ChemAxon
Polarizability17.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-2900000000-ff7c6eb395fa0dca0b1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9660000000-e6364fbc9b1f21523494Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-0a83b777d47c5cb70fe7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-fb7ac03eae1dde57ce15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9600000000-60f1209a7a4a3d467962Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-2cf3a59cab7a65c95fddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-602677c1a8ab9f590697Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l5-8900000000-a8967686dff6bf46df57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-1825467fa9ff0e5c1aa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-fe86bc056d5218edfccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-5900000000-4f1700d7e2571d2c2548Spectrum
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 IDFDB013860
KNApSAcK IDC00003062
Chemspider ID3485
KEGG Compound IDC09904
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHinokitiol
METLIN IDNot Available
PubChem Compound3611
PDB IDNot Available
ChEBI ID10447
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhao J, Sakai K: Multiple signalling pathways mediate fungal elicitor-induced beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures. J Exp Bot. 2003 Feb;54(383):647-56. [PubMed:12554707 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .