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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:10:50 UTC

Update Date

2022-03-07 02:54:47 UTC

HMDB ID

HMDB0036114

Secondary Accession Numbers

HMDB36114

Metabolite Identification

Common Name

(-)-3-Thujone

Description

(-)-3-Thujone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (-)-3-thujone is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on (-)-3-Thujone.

Structure

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

COMPND    HMDB0036114
HETATM    1  C1  UNL     1       2.366   1.147   0.849  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.687   0.375  -0.266  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.414  -0.935  -0.485  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.225   0.172   0.016  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.597   1.404   0.178  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.879   1.209  -0.524  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.679   2.082  -0.743  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.986  -0.231  -0.894  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.863  -0.896   0.148  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.604  -0.776  -0.719  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.234  -1.038   0.730  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.081   0.810   1.849  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.456   1.092   0.750  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.104   2.239   0.798  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.820   0.979  -1.188  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.825  -1.263   0.492  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.306  -0.802  -1.161  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.784  -1.700  -0.967  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.068   2.247  -0.356  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.709   1.750   1.219  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.385  -0.364  -1.918  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.893  -1.076  -0.243  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.954  -0.281   1.073  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.421  -1.877   0.491  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.234  -1.446  -1.506  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.404  -1.930   0.853  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.964  -0.893   1.525  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   10   11
CONECT    5    6   19   20
CONECT    6    7    7    8
CONECT    8    9   10   21
CONECT    9   22   23   24
CONECT   10   11   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,4R,5S)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one	ChEBI
(-)-beta-Thujone	HMDB
(-)-cis-Thujone	HMDB
(-)-Isothujone	HMDB
L-Isothujone	HMDB
(-)-b-Thujone	Generator
(-)-Β-thujone	Generator

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

Traditional Name

(-)-β-thujone

CAS Registry Number

Not Available

SMILES

CC(C)[C@]12C[C@H]1[C@@H](C)C(=O)C2

InChI Identifier

InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8+,10-/m1/s1

InChI Key

USMNOWBWPHYOEA-KHQFGBGNSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Thujane monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

beta-thujone (CHEBI:50046 )
Bicyclic monoterpenoids (LMPR0102120040 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036114)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036114)

Source

Endogenous

Endogenous (HMDB: HMDB0036114)

Animal

Animal (HMDB: HMDB0036114)

Exogenous

Food

Food (HMDB: HMDB0036114)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036114)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036114)

Cellular process

Cell signaling (HMDB: HMDB0036114)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036114)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036114)

Nutrient

Nutrient (HMDB: HMDB0036114)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036114)

Emulsifier (HMDB: HMDB0036114)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	1.74	ALOGPS
logP	2.28	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.54 m³·mol⁻¹	ChemAxon
Polarizability	18.02 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	137.344	31661259
DarkChem	[M-H]-	135.953	31661259
DeepCCS	[M-2H]-	172.996	30932474
DeepCCS	[M+Na]+	147.996	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	137.9	32859911
AllCCS	[M+Na-2H]-	139.1	32859911
AllCCS	[M+HCOO]-	140.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-3-Thujone	CC(C)[C@]12C[C@H]1[C@@H](C)C(=O)C2	1519.4	Standard polar	33892256
(-)-3-Thujone	CC(C)[C@]12C[C@H]1[C@@H](C)C(=O)C2	1130.1	Standard non polar	33892256
(-)-3-Thujone	CC(C)[C@]12C[C@H]1[C@@H](C)C(=O)C2	1097.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-3-Thujone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C[C@@]2(C(C)C)C[C@@H]12	1290.3	Semi standard non polar	33892256
(-)-3-Thujone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C[C@@]2(C(C)C)C[C@@H]12	1341.1	Standard non polar	33892256
(-)-3-Thujone,1TMS,isomer #2	CC(C)[C@@]12C=C(O[Si](C)(C)C)[C@H](C)[C@@H]1C2	1220.7	Semi standard non polar	33892256
(-)-3-Thujone,1TMS,isomer #2	CC(C)[C@@]12C=C(O[Si](C)(C)C)[C@H](C)[C@@H]1C2	1300.1	Standard non polar	33892256
(-)-3-Thujone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@]2(C(C)C)C[C@@H]12	1520.9	Semi standard non polar	33892256
(-)-3-Thujone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C[C@@]2(C(C)C)C[C@@H]12	1549.2	Standard non polar	33892256
(-)-3-Thujone,1TBDMS,isomer #2	CC(C)[C@@]12C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)[C@@H]1C2	1436.0	Semi standard non polar	33892256
(-)-3-Thujone,1TBDMS,isomer #2	CC(C)[C@@]12C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)[C@@H]1C2	1487.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-3-Thujone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ou-9300000000-5ac67463cc6dff4e26c5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-3-Thujone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-3-Thujone 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 10V, Positive-QTOF	splash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 20V, Positive-QTOF	splash10-0udi-7900000000-e4ab468ffb3afaf16129	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 40V, Positive-QTOF	splash10-0pe9-9000000000-960a6c7d4901afec9233	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 10V, Negative-QTOF	splash10-0udi-0900000000-07a82b9f8d15764ed904	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 20V, Negative-QTOF	splash10-0udi-0900000000-65761ceb0d88aa809b6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 40V, Negative-QTOF	splash10-0006-9500000000-4023ebf09d9995d37111	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 10V, Positive-QTOF	splash10-0006-8900000000-a32be7e7fd99fd0b8b23	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 20V, Positive-QTOF	splash10-000x-9300000000-eac02498908e1d67934a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 40V, Positive-QTOF	splash10-0006-9400000000-22a79a891aa2c60d074e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 20V, Negative-QTOF	splash10-0udi-0900000000-e8b89c21a7958e185278	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-3-Thujone 40V, Negative-QTOF	splash10-0pdl-7900000000-5c5ad8968d995b2431ac	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB014961

KNApSAcK ID

Not Available

Chemspider ID

5026861

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6553876

PDB ID

Not Available

ChEBI ID

50046

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (-)-3-Thujone (HMDB0036114)

MOL for HMDB0036114 ((-)-3-Thujone)

3D MOL for HMDB0036114 ((-)-3-Thujone)

3D SDF for HMDB0036114 ((-)-3-Thujone)

3D-SDF for HMDB0036114 ((-)-3-Thujone)

PDB for HMDB0036114 ((-)-3-Thujone)

3D PDB for HMDB0036114 ((-)-3-Thujone)

SMILES for HMDB0036114 ((-)-3-Thujone)

INCHI for HMDB0036114 ((-)-3-Thujone)

Structure for HMDB0036114 ((-)-3-Thujone)

3D Structure for HMDB0036114 ((-)-3-Thujone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra