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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:10:46 UTC

Update Date

2023-02-21 17:25:05 UTC

HMDB ID

HMDB0036113

Secondary Accession Numbers

HMDB36113

Metabolite Identification

Common Name

(+)-3-Thujone

Description

(+)-3-Thujone, also known as beta-thujone or β-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 significant number of articles have been published on (+)-3-Thujone.

Structure

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

COMPND    HMDB0036113
HETATM    1  C1  UNL     1      -2.712  -0.771  -0.041  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.682   0.352   0.095  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.099   1.578  -0.631  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.327  -0.159  -0.220  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.151  -1.289   0.672  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.615  -1.263   0.487  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.382  -2.177   0.508  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.947   0.166   0.266  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.305   0.362  -0.341  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.822   0.631  -0.606  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.192  -0.237  -1.620  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.655  -0.386   0.395  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.846  -1.083  -1.078  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.331  -1.632   0.582  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.700   0.602   1.198  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.938   1.369  -1.358  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.538   2.361   0.056  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.319   2.085  -1.202  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.105  -1.009   1.711  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.312  -2.239   0.348  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.850   0.728   1.240  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.979   0.702   0.500  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.358   1.142  -1.102  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.748  -0.611  -0.667  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.821   1.711  -0.818  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.727  -1.174  -1.955  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.335   0.243  -2.458  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
(+)-Isothujone	ChEBI
(1S,4S,5R)-(+)-3-Thujanone	ChEBI
(1S,4S,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one	ChEBI
[1S-(1alpha,4beta,5alpha)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	ChEBI
beta-Thujone	ChEBI
D-beta-Thujone	ChEBI
D-Isothujone	ChEBI
trans-Thujone	ChEBI
[1S-(1a,4b,5a)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	Generator
[1S-(1Α,4β,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	Generator
b-Thujone	Generator
Β-thujone	Generator
D-b-Thujone	Generator
D-Β-thujone	Generator
(+)-b-Thujone	HMDB, Generator
(+)-beta-Thujone	HMDB
(+)-cis-Thujone	HMDB
(+)-Thujone	HMDB
-Thujone	HMDB
D-beta	HMDB
Isothujone	HMDB
(+)-3-Thujone	ChEBI
(+)-Β-thujone	Generator
alpha-Thujone	MeSH
cis-Thujone	MeSH
Thujone	MeSH
(-)-Thujone	MeSH
3-Isothujone	MeSH
3-Thujanone	MeSH
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomer	MeSH
alpha, beta-Thujone	MeSH
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomer	MeSH
beta-Thujone, (1alpha,4alpha,5alpha)-isomer	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

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

Traditional Name

(+)-β-thujone

CAS Registry Number

471-15-8

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-/m0/s1

InChI Key

USMNOWBWPHYOEA-XKSSXDPKSA-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:50045 )
Bicyclic monoterpenoids (LMPR0102120039 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036113)

Source

Endogenous

Endogenous (HMDB: HMDB0036113)

Plant

Plant (HMDB: HMDB0036113)

Animal

Animal (HMDB: HMDB0036113)

Exogenous

Food

Food (HMDB: HMDB0036113)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Herb

Exogenous (HMDB: HMDB0036113)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036113)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036113)

Lipid metabolism pathway (HMDB: HMDB0036113)

Cellular process

Cell signaling (HMDB: HMDB0036113)

Biochemical process

Lipid transport (HMDB: HMDB0036113)

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036113)

Abortifacient (HMDB: HMDB0036113)

Agriculture

Pesticide (HMDB: HMDB0036113)

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	407.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
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]+	137.209	31661259
DarkChem	[M-H]-	136.508	31661259
DeepCCS	[M-2H]-	173.9	30932474
DeepCCS	[M+Na]+	148.958	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
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2041.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	518.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	185.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	299.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	579.8 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	674.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1121.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	408.4 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	1338.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	385.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	383.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	445.3 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	24.1 seconds	40023050

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

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91456

PDB ID

Not Available

ChEBI ID

50045

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1384741

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jug-Dujakovic M, Ristic M, Pljevljakusic D, Dajic-Stevanovic Z, Liber Z, Hancevic K, Radic T, Satovic Z: High diversity of indigenous populations of dalmatian sage (Salvia officinalis L.) in essential-oil composition. Chem Biodivers. 2012 Oct;9(10):2309-23. doi: 10.1002/cbdv.201200131. [PubMed:23081929 ]
Walch SG, Lachenmeier DW, Kuballa T, Stuhlinger W, Monakhova YB: Holistic Control of Herbal Teas and Tinctures Based on Sage (Salvia officinalis L.) for Compounds with Beneficial and Adverse Effects using NMR Spectroscopy. Anal Chem Insights. 2012;7:1-12. doi: 10.4137/ACI.S8946. Epub 2012 Mar 21. [PubMed:22493561 ]
Satyal P, Paudel P, Kafle A, Pokharel SK, Lamichhane B, Dosoky NS, Moriarity DM, Setzer WN: Bioactivities of volatile components from Nepalese Artemisia species. Nat Prod Commun. 2012 Dec;7(12):1651-8. [PubMed:23413575 ]
Rice KC, Wilson RS: (-)-3-Isothujone, a small nonnitrogenous molecule with antinociceptive activity in mice. J Med Chem. 1976 Aug;19(8):1054-7. [PubMed:966252 ]
Wise ML, Savage TJ, Katahira E, Croteau R: Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. J Biol Chem. 1998 Jun 12;273(24):14891-9. [PubMed:9614092 ]
Haider SZ, Andola HC, Mohan M: Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone. Indian J Pharm Sci. 2012 May;74(3):265-7. doi: 10.4103/0250-474X.106074. [PubMed:23439844 ]
Santos-Gomes PC, Fernandes-Ferreira M: Essential oils produced by in vitro shoots of sage (Salvia officinalis L.). J Agric Food Chem. 2003 Apr 9;51(8):2260-6. [PubMed:12670167 ]
Dehal SS, Croteau R: Metabolism of monoterpenes: specificity of the dehydrogenases responsible for the biosynthesis of camphor, 3-thujone, and 3-isothujone. Arch Biochem Biophys. 1987 Oct;258(1):287-91. [PubMed:3310901 ]
Kolassa N: Menthol differs from other terpenic essential oil constituents. Regul Toxicol Pharmacol. 2013 Feb;65(1):115-8. doi: 10.1016/j.yrtph.2012.11.009. Epub 2012 Dec 1. [PubMed:23207345 ]
Tayade AB, Dhar P, Kumar J, Sharma M, Chauhan RS, Chaurasia OP, Srivastava RB: Chemometric profile of root extracts of Rhodiola imbricata Edgew. with hyphenated gas chromatography mass spectrometric technique. PLoS One. 2013;8(1):e52797. doi: 10.1371/journal.pone.0052797. Epub 2013 Jan 10. [PubMed:23326358 ]
Raut JS, Shinde RB, Chauhan NM, Karuppayil SM: Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans. Biofouling. 2013;29(1):87-96. doi: 10.1080/08927014.2012.749398. [PubMed:23216018 ]
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 (HMDB0036113)

MOL for HMDB0036113 ((+)-3-Thujone)

3D MOL for HMDB0036113 ((+)-3-Thujone)

3D SDF for HMDB0036113 ((+)-3-Thujone)

3D-SDF for HMDB0036113 ((+)-3-Thujone)

PDB for HMDB0036113 ((+)-3-Thujone)

3D PDB for HMDB0036113 ((+)-3-Thujone)

SMILES for HMDB0036113 ((+)-3-Thujone)

INCHI for HMDB0036113 ((+)-3-Thujone)

Structure for HMDB0036113 ((+)-3-Thujone)

3D Structure for HMDB0036113 ((+)-3-Thujone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized