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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:09:48 UTC
Update Date2022-03-07 02:54:24 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. beta-Thujaplicin is a phenolic and woody tasting compound. beta-Thujaplicin has been detected, but not quantified in, fruits. This could make beta-thujaplicin a potential biomarker for the consumption of these foods. beta-Thujaplicin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on beta-Thujaplicin.
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-isopropyl- 2,4,6-cycloheptatriene-1-oneMeSH
beta-Thujaplicin, sodium saltMeSH
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-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
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

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point52 - 52.5 °CNot Available
Boiling Point140.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility1.2 mg/mL at 25 °CNot Available
LogP1.137 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.06731661259
DarkChem[M-H]-134.51431661259
DeepCCS[M+H]+137.81930932474
DeepCCS[M-H]-135.20630932474
DeepCCS[M-2H]-171.27730932474
DeepCCS[M+Na]+146.7930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-ThujaplicinCC(C)C1=CC(=O)C(O)=CC=C11981.0Standard polar33892256
beta-ThujaplicinCC(C)C1=CC(=O)C(O)=CC=C11526.9Standard non polar33892256
beta-ThujaplicinCC(C)C1=CC(=O)C(O)=CC=C11527.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Thujaplicin,1TMS,isomer #1CC(C)C1=CC(=O)C(O[Si](C)(C)C)=CC=C11634.2Semi standard non polar33892256
beta-Thujaplicin,1TBDMS,isomer #1CC(C)C1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=CC=C11877.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Thujaplicin GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-2900000000-ff7c6eb395fa0dca0b1c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Thujaplicin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9660000000-e6364fbc9b1f215234942017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Thujaplicin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Thujaplicin 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 - beta-Thujaplicin LC-ESI-QTOF , negative-QTOFsplash10-03di-0900000000-0a83b777d47c5cb70fe72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Thujaplicin LC-ESI-QTOF , negative-QTOFsplash10-0002-0900000000-fb7ac03eae1dde57ce152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Thujaplicin LC-ESI-QTOF , positive-QTOFsplash10-0002-9600000000-60f1209a7a4a3d4679622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Thujaplicin 30V, Negative-QTOFsplash10-0002-0900000000-fb7ac03eae1dde57ce152021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Positive-QTOFsplash10-014i-0900000000-2cf3a59cab7a65c95fdd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Positive-QTOFsplash10-014i-1900000000-602677c1a8ab9f5906972016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Positive-QTOFsplash10-00l5-8900000000-a8967686dff6bf46df572016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Negative-QTOFsplash10-03di-0900000000-1825467fa9ff0e5c1aa22016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Negative-QTOFsplash10-03di-0900000000-fe86bc056d5218edfcca2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Negative-QTOFsplash10-053u-5900000000-4f1700d7e2571d2c25482016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Positive-QTOFsplash10-014l-2900000000-478708776defcf78466a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Positive-QTOFsplash10-006t-1900000000-2060bea741e6c07954f92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Positive-QTOFsplash10-002f-9200000000-b596582d3b5b139424992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Negative-QTOFsplash10-03di-0900000000-8db47caa9667c101bd0f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Negative-QTOFsplash10-03di-0900000000-8475534962693d08c77e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Negative-QTOFsplash10-014l-9200000000-bb82c060a8ef6dee087c2021-09-24Wishart 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 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
MarkerDB IDNot Available
Good Scents IDrw1044801
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.. .