Thujone

Details

• Internal ID: 26ee907f-4d28-4476-b146-871e7648dcf5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
• SMILES (Canonical): CC1C2CC2(CC1=O)C(C)C
• SMILES (Isomeric): C[C@@H]1[C@H]2C[C@]2(CC1=O)C(C)C
• InChI: 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-MRTMQBJTSA-N
• Popularity: 1,253 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23 g/mol
• Exact Mass: 152.120115130 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.26
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 546-80-5
• alpha-(-)-Thujone
• (-)-alpha-thujone
• THUJONE
• Thujon
• l-Thujone
• (-)-3-Isothujone
• (-)-3-thujanone
• Absinthol
• dl-Thujone
• 3-Thujanone, (-)-
• (+-)-Isothujone
• racemic 3-Isothujone
• UNII-R0SQ9G0DU5
• EINECS 208-912-2
• NSC 93742
• BRN 4660369
• CCRIS 8582
• CHEBI:9577
• (1S,4R,5R)-thujan-3-one
• (1S,4R,5R)-(-)-3-thujanone
• 3-Thujanone, (+-)-
• Isothujone, (-)-
• R0SQ9G0DU5
• 3-Thujanone, (1S,4R,5R)-(-)-
• 59573-80-7
• DTXSID3026148
• Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-
• (-)-Thujone
• (1S,4R,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
• (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
• .alpha.-Thujone
• Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-
• Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1-alpha,4-alpha,5-alpha)-(+-)-
• 86HK1QRJ4K
• CHEBI:50040
• (1S,4R,5R)-1-isopropyl-4-methylbicyclo(3.1.0)hexan-3-one
• (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo(3.1.0)hexan-3-one
• NSC-93742
• L-alpha-Thujone
• (1S-(1alpha,4alpha,5alpha))-4-methyl-1-(1-methylethyl)bicyclo(3.1.0)hexan-3-one
• [1S-(1alpha,4alpha,5alpha)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one
• ??-Thujone
• MFCD00001313
• (-)-trans-Thujone
• (-)-a-Thujone
• ALFA-THUJONE
• (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
• (-)- alpha -Thujone
• (-)-alpha,beta-Thujone
• a-(-)-THUJONE
• D0TV0V
• THUJONE, .ALPHA.-
• MLS001065588
• SCHEMBL122447
• .ALPHA.-THUJONE [MI]
• DTXCID206148
• GTPL5344
• CHEMBL1444078
• HMS3039B05
• (1R,2R,5S)-5-isopropyl-2-methyl-bicyclo[3.1.0]hexan-3-one
• (1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
• Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1.alpha.,4.alpha.,5.alpha.)]-
• Tox21_200868
• (-)-Thujone ((-)-alpha-Thujone)
• (1S,4R,5R)- 3-THUJANONE
• AKOS040759330
• LMPR0102120019
• LS-2152
• NCGC00091438-01
• NCGC00091438-02
• NCGC00164360-01
• NCGC00258422-01
• CAS-546-80-5
• MS-22862
• SMR000568469
• (-)-alpha-Thujone, >=96.0% (GC)
• HY-121618
• LS-153761
• CS-0082886
• C09906
• Q421838
• 1 - isopropyl - 4 - methylbicyclo(3.1.0)hexan - 3 - one
• (-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
• BICYCLO(3.1.0)HEXAN-3-ONE, 4-METHYL-1-(1-METHYLETHYL)-, (1S,5R)-
• Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S-(1alpha,4alpha,5alpha))-
• Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1?,4?,5?)]-
• Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1-alpha,4-alpha,5-alpha)-(+-)- (9CI)
• Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1.alpha.,4.alpha.,5.alpha.)-(.+.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	-	0.6774	67.74%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5631	56.31%
OATP2B1 inhibitior	-	0.8490	84.90%
OATP1B1 inhibitior	+	0.9491	94.91%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9031	90.31%
P-glycoprotein inhibitior	-	0.9518	95.18%
P-glycoprotein substrate	-	0.9224	92.24%
CYP3A4 substrate	-	0.5690	56.90%
CYP2C9 substrate	-	0.7813	78.13%
CYP2D6 substrate	-	0.7531	75.31%
CYP3A4 inhibition	-	0.9045	90.45%
CYP2C9 inhibition	-	0.8726	87.26%
CYP2C19 inhibition	-	0.8201	82.01%
CYP2D6 inhibition	-	0.9607	96.07%
CYP1A2 inhibition	-	0.8544	85.44%
CYP2C8 inhibition	-	0.9947	99.47%
CYP inhibitory promiscuity	-	0.9607	96.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7817	78.17%
Carcinogenicity (trinary)	Non-required	0.6220	62.20%
Eye corrosion	-	0.8039	80.39%
Eye irritation	+	0.9012	90.12%
Skin irritation	+	0.7647	76.47%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7501	75.01%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	+	0.8403	84.03%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	II	0.7356	73.56%
Estrogen receptor binding	-	0.9129	91.29%
Androgen receptor binding	-	0.5830	58.30%
Thyroid receptor binding	-	0.8753	87.53%
Glucocorticoid receptor binding	-	0.9044	90.44%
Aromatase binding	-	0.8562	85.62%
PPAR gamma	-	0.6934	69.34%
Honey bee toxicity	-	0.7995	79.95%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9150	91.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.88%	97.25%
CHEMBL299	P17252	Protein kinase C alpha	88.52%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.20%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.03%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.96%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.13%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.09%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.98%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.15%	90.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.06%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	82.05%	94.75%

Plants that contains it

• Achillea abrotanoides
• Achillea erba-rotta
• Achillea fragrantissima
• Achillea grandifolia
• Achillea millefolium
• Achillea ptarmica subsp. ptarmica
• Aloysia citrodora
• Alpinia zerumbet
• Artemisia absinthium
• Artemisia afra
• Artemisia annua
• Artemisia arborescens
• Artemisia argyi
• Artemisia campestris subsp. campestris
• Artemisia douglasiana
• Artemisia gmelinii
• Artemisia halophila
• Artemisia jacutica
• Artemisia ludoviciana
• Artemisia montana
• Artemisia princeps
• Artemisia salsoloides
• Artemisia sericea
• Artemisia thuscula
• Artemisia tridentata
• Artemisia vulgaris
• Brucea javanica
• Chrysanthemum indicum
• Cleonia lusitanica
• Clinopodium grandiflorum
• Commiphora gurreh
• Cyclotrichium niveum
• Hyssopus officinalis
• Juniperus foetidissima
• Melaleuca alternifolia
• Mentha arvensis
• Mentha canadensis
• Micromeria biflora
• Micromeria juliana
• Origanum majorana
• Origanum vulgare
• Phlomis fruticosa
• Rhododendron mucronulatum
• Salvia absconditiflora
• Salvia cuspidata subsp. gilliesii
• Salvia fruticosa
• Salvia officinalis
• Salvia pisidica
• Salvia pomifera
• Salvia sclarea
• Salvia viscida
• Seriphidium baldshuanicum
• Sideritis tragoriganum
• Tanacetum millefolium
• Tanacetum vulgare
• Taxus canadensis
• Thuja occidentalis
• Thuja plicata
• Thymus carnosus
• Thymus fedtschenkoi
• Thymus zygioides
• Vitex agnus-castus

Cross-Links

• PubChem: 261491
• NPASS: NPC83187
• ChEMBL: CHEMBL1444078
• LOTUS: LTS0197087
• wikiData: Q421838