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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 03:19:30 UTC

Update Date

2022-09-22 18:34:27 UTC

HMDB ID

HMDB0041631

Secondary Accession Numbers

HMDB41631

Metabolite Identification

Common Name

3-Thujanone

Description

3-Thujanone is found in common sage. Thujone is a ketone and a monoterpene that occurs naturally in two diastereomeric forms: (-)-alpha-thujone and (+)-beta-thujone. It has a menthol odor. In addition to (-)-alpha-thujone and (+)-beta-thujone, there are their enantiomeric forms, (+)-alpha-thujone and (-)-beta-thujone. (Wikipedia ).

Structure

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

COMPND    HMDB0041631
HETATM    1  C1  UNL     1       3.032  -0.325  -1.003  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.094   0.097   0.089  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.486   1.403  -0.214  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.044   2.341  -0.707  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.033   1.386   0.195  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.299  -0.045   0.430  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.648  -0.596   0.041  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.944  -0.471  -1.417  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.691   0.219   0.795  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.276  -0.687   1.664  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.938  -0.821   0.285  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.570  -0.378  -1.994  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.830   0.462  -1.062  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.539  -1.265  -0.792  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.686   0.111   1.040  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.098   1.929   1.173  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.516   1.847  -0.624  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.770  -1.644   0.356  1.00  0.00           H  
HETATM   19  H8  UNL     1      -3.035  -0.708  -1.548  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.832   0.572  -1.778  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.386  -1.200  -2.021  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.634   0.207   0.220  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.890  -0.213   1.798  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.344   1.259   0.828  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.154  -1.647   2.024  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.727  -0.023   2.402  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.987  -1.811  -0.179  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   11   15
CONECT    3    4    4    5
CONECT    5    6   16   17
CONECT    6    7   10   11
CONECT    7    8    9   18
CONECT    8   19   20   21
CONECT    9   22   23   24
CONECT   10   11   25   26
CONECT   11   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one	ChEBI
(+)-Thujone	MeSH
(-)-Thujone	MeSH
3-Isothujone	MeSH
alpha, beta-Thujone	MeSH
alpha-Thujone	MeSH
beta-Thujone	MeSH
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomer	MeSH
beta-Thujone, (1alpha,4alpha,5alpha)-isomer	MeSH
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomer	MeSH
cis-Thujone	MeSH
Thujone	MeSH
3-Thujanone	ChEBI
(+-)-Isothujone	HMDB
(+-)-Thujone	HMDB
1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one	HMDB
3-Sabinanone	HMDB
4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one, 9ci	HMDB
Absinthone	HMDB
Chrysanthone	HMDB
Salvone	HMDB
Tanacetone	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

IUPAC Name

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

Traditional Name

3-isothujone

CAS Registry Number

1125-12-8

SMILES

CC(C)C12CC1C(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

InChI Key

USMNOWBWPHYOEA-UHFFFAOYSA-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

cyclic terpene ketone (CHEBI:50040 )
thujane monoterpenoid (CHEBI:50040 )
a monoterpenol (CPD-13996 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	200.00 to 201.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	407.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.044 (est)	The Good Scents Company Information System

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	17.98 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]+	135.877	31661259
DarkChem	[M-H]-	129.625	31661259
DeepCCS	[M-2H]-	177.649	30932474
DeepCCS	[M+Na]+	153.116	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 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.	4.28 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0176 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.13 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Thujanone	CC(C)C12CC1C(C)C(=O)C2	1516.6	Standard polar	33892256
3-Thujanone	CC(C)C12CC1C(C)C(=O)C2	1117.3	Standard non polar	33892256
3-Thujanone	CC(C)C12CC1C(C)C(=O)C2	1104.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Thujanone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC2(C(C)C)CC12	1297.9	Semi standard non polar	33892256
3-Thujanone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC2(C(C)C)CC12	1311.5	Standard non polar	33892256
3-Thujanone,1TMS,isomer #2	CC1C(O[Si](C)(C)C)=CC2(C(C)C)CC12	1229.0	Semi standard non polar	33892256
3-Thujanone,1TMS,isomer #2	CC1C(O[Si](C)(C)C)=CC2(C(C)C)CC12	1286.8	Standard non polar	33892256
3-Thujanone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC2(C(C)C)CC12	1547.8	Semi standard non polar	33892256
3-Thujanone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC2(C(C)C)CC12	1522.3	Standard non polar	33892256
3-Thujanone,1TBDMS,isomer #2	CC1C(O[Si](C)(C)C(C)(C)C)=CC2(C(C)C)CC12	1446.4	Semi standard non polar	33892256
3-Thujanone,1TBDMS,isomer #2	CC1C(O[Si](C)(C)C(C)(C)C)=CC2(C(C)C)CC12	1487.0	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-Thujanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9300000000-eec889eda42ade9a448b	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Thujanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Thujanone 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-Thujanone 10V, Positive-QTOF	splash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 20V, Positive-QTOF	splash10-0udi-7900000000-6bfa698b489e2584c2e8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 40V, Positive-QTOF	splash10-0pe9-9000000000-c1faae6eaa2d099fe95f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 10V, Negative-QTOF	splash10-0udi-0900000000-07a82b9f8d15764ed904	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 20V, Negative-QTOF	splash10-0udi-0900000000-65761ceb0d88aa809b6a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 40V, Negative-QTOF	splash10-0006-9500000000-4023ebf09d9995d37111	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 10V, Positive-QTOF	splash10-0006-8900000000-a32be7e7fd99fd0b8b23	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 20V, Positive-QTOF	splash10-000x-9300000000-eac02498908e1d67934a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 40V, Positive-QTOF	splash10-0006-9400000000-22a79a891aa2c60d074e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 20V, Negative-QTOF	splash10-0udi-0900000000-e8b89c21a7958e185278	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Thujanone 40V, Negative-QTOF	splash10-0pdl-7900000000-5c5ad8968d995b2431ac	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB021854

KNApSAcK ID

C00024784

Chemspider ID

10561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thujone

METLIN ID

Not Available

PubChem Compound

11027

PDB ID

Not Available

ChEBI ID

50040

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1137041

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-Thujanone (HMDB0041631)

MOL for HMDB0041631 (3-Thujanone)

3D MOL for HMDB0041631 (3-Thujanone)

3D SDF for HMDB0041631 (3-Thujanone)

3D-SDF for HMDB0041631 (3-Thujanone)

PDB for HMDB0041631 (3-Thujanone)

3D PDB for HMDB0041631 (3-Thujanone)

SMILES for HMDB0041631 (3-Thujanone)

INCHI for HMDB0041631 (3-Thujanone)

Structure for HMDB0041631 (3-Thujanone)

3D Structure for HMDB0041631 (3-Thujanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra