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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:09:48 UTC

Update Date

2023-02-21 17:24:41 UTC

HMDB ID

HMDB0035213

Secondary Accession Numbers

HMDB35213

Metabolite Identification

Common Name

beta-Thujaplicin

Description

beta-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.933   4.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.265   4.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.986   1.877   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.211   1.877   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.161  -2.216   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.633   0.032   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3    9                                                       
CONECT    6    8   10                                                       
CONECT    7    1    2    8                                                  
CONECT    8    4    6    7                                                  
CONECT    9    5   10   11                                                  
CONECT   10    6    9   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-4-isopropyl-cyclohepta2,4,6-trien-1-one	ChEBI
4-Isopropyltropolone	ChEBI
Hinokitiol	ChEBI
b-Thujaplicin	Generator
Β-thujaplicin	Generator
2-Hydroxy-4-isopropyl- 2,4,6-cycloheptatriene-1-one	MeSH
beta-Thujaplicin, sodium salt	MeSH
2-Hydroxy-4(6)-(1-methylethyl)-2,4,6-cycloheptatrien-1-one, 9ci	HMDB
2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one	HMDB
2-Hydroxy-4-isopropyl-2,4, 6-cycloheptatrien-1-one	HMDB
2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-one	HMDB
2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one	HMDB
2-Hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-one	HMDB
4(6)-Isopropyltropolone	HMDB
4-Isopropyl-tropolone	HMDB
alpha-Thujaplicin	HMDB
beta -Isopropyltropolon	HMDB
beta -Thujaplicin	HMDB
beta -Thujaplicine	HMDB
beta-Isopropyltropolon	HMDB
beta-Isopropyltropolone	HMDB
beta-Thujaplicine	HMDB
Hinokitiol 4-isopropyltropolone	HMDB
Hinokitol	HMDB
Isopropyltropolone	HMDB
Thujaplicin, beta	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

2-hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one

Traditional Name

hinokitiol

CAS Registry Number

499-44-5

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 Key

FUWUEFKEXZQKKA-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.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Tropolones

Direct Parent

Tropolones

Alternative Parents

Substituents

Tropolone
Cyclic ketone
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cyclic ketone (CHEBI:10447 )
enol (CHEBI:10447 )
monoterpenoid (CHEBI:10447 )
Cyclic monoterpenes (C09904 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0035213)
Cytoplasm (HMDB: HMDB0035213)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035213)

Source

Exogenous

Exogenous (HMDB: HMDB0035213)

Food

Food (HMDB: HMDB0035213)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0035213)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035213)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	52 - 52.5 °C	Not Available
Boiling Point	140.00 °C. @ 10.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.2 mg/mL at 25 °C	Not Available
LogP	1.137 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	1.8	ALOGPS
logP	2.06	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.44	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.55 m³·mol⁻¹	ChemAxon
Polarizability	17.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.067	31661259
DarkChem	[M-H]-	134.514	31661259
DeepCCS	[M+H]+	137.819	30932474
DeepCCS	[M-H]-	135.206	30932474
DeepCCS	[M-2H]-	171.277	30932474
DeepCCS	[M+Na]+	146.79	30932474
AllCCS	[M+H]+	133.2	32859911
AllCCS	[M+H-H2O]+	128.7	32859911
AllCCS	[M+NH4]+	137.4	32859911
AllCCS	[M+Na]+	138.6	32859911
AllCCS	[M-H]-	135.0	32859911
AllCCS	[M+Na-2H]-	136.1	32859911
AllCCS	[M+HCOO]-	137.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.55 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8954 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.4 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1987.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	364.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	155.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	221.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	570.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	496.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1052.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	405.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1135.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	345.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	237.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	40.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Thujaplicin	CC(C)C1=CC(=O)C(O)=CC=C1	1981.0	Standard polar	33892256
beta-Thujaplicin	CC(C)C1=CC(=O)C(O)=CC=C1	1526.9	Standard non polar	33892256
beta-Thujaplicin	CC(C)C1=CC(=O)C(O)=CC=C1	1527.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-Thujaplicin,1TMS,isomer #1	CC(C)C1=CC(=O)C(O[Si](C)(C)C)=CC=C1	1634.2	Semi standard non polar	33892256
beta-Thujaplicin,1TBDMS,isomer #1	CC(C)C1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=CC=C1	1877.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Thujaplicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-2900000000-ff7c6eb395fa0dca0b1c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Thujaplicin GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9660000000-e6364fbc9b1f21523494	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Thujaplicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Thujaplicin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Thujaplicin LC-ESI-QTOF , negative-QTOF	splash10-03di-0900000000-0a83b777d47c5cb70fe7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Thujaplicin LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-fb7ac03eae1dde57ce15	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Thujaplicin LC-ESI-QTOF , positive-QTOF	splash10-0002-9600000000-60f1209a7a4a3d467962	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Thujaplicin 30V, Negative-QTOF	splash10-0002-0900000000-fb7ac03eae1dde57ce15	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Positive-QTOF	splash10-014i-0900000000-2cf3a59cab7a65c95fdd	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Positive-QTOF	splash10-014i-1900000000-602677c1a8ab9f590697	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Positive-QTOF	splash10-00l5-8900000000-a8967686dff6bf46df57	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Negative-QTOF	splash10-03di-0900000000-1825467fa9ff0e5c1aa2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Negative-QTOF	splash10-03di-0900000000-fe86bc056d5218edfcca	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Negative-QTOF	splash10-053u-5900000000-4f1700d7e2571d2c2548	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Positive-QTOF	splash10-014l-2900000000-478708776defcf78466a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Positive-QTOF	splash10-006t-1900000000-2060bea741e6c07954f9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Positive-QTOF	splash10-002f-9200000000-b596582d3b5b13942499	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 10V, Negative-QTOF	splash10-03di-0900000000-8db47caa9667c101bd0f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 20V, Negative-QTOF	splash10-03di-0900000000-8475534962693d08c77e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Thujaplicin 40V, Negative-QTOF	splash10-014l-9200000000-bb82c060a8ef6dee087c	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hinokitiol

METLIN ID

Not Available

PubChem Compound

3611

PDB ID

Not Available

ChEBI ID

10447

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1044801

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for beta-Thujaplicin (HMDB0035213)

MOL for HMDB0035213 (beta-Thujaplicin)

3D MOL for HMDB0035213 (beta-Thujaplicin)

3D SDF for HMDB0035213 (beta-Thujaplicin)

3D-SDF for HMDB0035213 (beta-Thujaplicin)

PDB for HMDB0035213 (beta-Thujaplicin)

3D PDB for HMDB0035213 (beta-Thujaplicin)

SMILES for HMDB0035213 (beta-Thujaplicin)

INCHI for HMDB0035213 (beta-Thujaplicin)

Structure for HMDB0035213 (beta-Thujaplicin)

3D Structure for HMDB0035213 (beta-Thujaplicin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra