Select a section from the left sidebar
Alpha-thujone
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene
| Canonical Smiles | O=C1C[C@]2([C@@H]([C@H]1C)C2)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 |
| InChIKey | USMNOWBWPHYOEA-MRTMQBJTSA-N |
| Formula | C10H16O |
| HBA | 1 |
| HBD | 0 |
| MW | 152.24 |
| Rotatable Bonds | 1 |
| TPSA | 17.07 |
| LogP | 2.26 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 152.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia herba-alba | Asteraceae | Plantae | 72329 |
| 2 | Artemisia arborescens | Asteraceae | Plantae | 72386 |
| 3 | Artemisia herba | Asteraceae | Plantae | 268028 |
| 4 | Tetraclinis articulata | Cupressaceae | Plantae | 13717 |
| 5 | Tetradenia riparia | Lamiaceae | Plantae | 992795 |
Showing of synonyms
Alpha-thujone
(-)-alpha-thujone
THUJONE
Thujon
L-Thujone
(-)-3-Isothujone
(-)-3-thujanone
Absinthol
UNII-R0SQ9G0DU5
EINECS 208-912-2
NSC 93742
BRN 4660369
CCRIS 8582
CHEBI:9577
(1S,4R,5R)-thujan-3-one
3-Thujanone, (-)-
(1S,4R,5R)-(-)-3-thujanone
(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
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
(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
(-)-alpha,beta-Thujone
BICYCLO(3.1.0)HEXAN-3-ONE, 4-METHYL-1-(1-METHYLETHYL)-, (1S,5R)-
4-methyl-1-(propan-2-yl)bicyclo(3.1.0)hexan-3-one
546-80-5
Alpha-(-)-Thujone
(+-)-Isothujone
MFCD00001313
59573-80-7
R0SQ9G0DU5
3-Thujanone, (1S,4R,5R)-(-)-
Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-
DTXSID3026148
(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,4R,5R)-
(-)-Thujone
(1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
Dl-Thujone
Racemic 3-Isothujone
.alpha.-Thujone
(-)-|A-Thujone
3-Thujanone, (+-)-
NSC-93742
L-alpha-Thujone
??-Thujone
(-)-trans-Thujone
(-)-a-Thujone
ALFA-THUJONE
(?)-|A-Thujone
(-)- alpha -Thujone
A-(-)-THUJONE
THUJONE, .ALPHA.-
MLS001065588
SCHEMBL122447
.ALPHA.-THUJONE [MI]
DTXCID206148
GTPL5344
CHEMBL1444078
USMNOWBWPHYOEA-MRTMQBJTSA-N
HMS3039B05
(1R,2R,5S)-5-isopropyl-2-methyl-bicyclo[3.1.0]hexan-3-one
Tox21_200868
(-)-Thujone ((-)-alpha-Thujone)
MSK163943
(1S,4R,5R)- 3-THUJANONE
AKOS040759330
LMPR0102120019
Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1-alpha,4-alpha,5-alpha)-(+-)-
NCGC00091438-01
NCGC00091438-02
NCGC00164360-01
NCGC00258422-01
CAS-546-80-5
MS-22862
SMR000568469
(-)-alpha-Thujone, >=96.0% (GC)
1ST163943
HY-121618
CS-0082886
NS00003614
C09906
Q421838
(-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
- Abderrahim A, Belhamel K, et al. (2010). Chemical composition of the essential oil from Artemisia arborescens L. growing wild in Algeria.. Records of Natural Products,2010,4(1),87-90. [View]
- Giordani R, Hadef Y, et al. (2008). Compositions and antifungal activities of essential oils of some Algerian aromatic plants.. Fitoterapia,2008,79,199 -203. [View] [PubMed]
- Belhattab R, Amor L, et al. (2014). Essential oil from Artemisia herba-alba Asso grown wild in Algeria: variability assessment and comparison with an updated literature survey.. Arabian Journal of Chemistry,2014,7,243-251. [View]
- Zidane A, Tits M, et al. (2014). Phytochemical analysis of Tetraclinis articula in relation to its vasorelaxant property. Journal of Materials and Environmental Sciences,2014,5(5),1368-1375. [View]
- Omolo MO, Okinyo D, et al. (2004). Repellency of essential oils of some Kenyan plants against Anopheles gambiae. Phytochemistry,2004,65(20),2797-2802. [View] [PubMed]
Pubchem:
261491
Cas:
546-80-5
Zinc:
ZINC000004098408
Kegg Ligand:
C09906
Chebi:
9577
Nmrshiftdb2:
40265319
Metabolights:
MTBLC9577
Chembl:
CHEMBL1444078
Comptox:
DTXSID3026148
CPRiL:
70650
SMILES: C12C(C1)CC(=O)C2
Level: 0
Mol. Weight: 152.24 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.5
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.240
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.430
- Plasma Protein Binding
- 39.68
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 13.050
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.040
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.370
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.450
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 1.580
- Rat (Acute)
- 2.360
- Rat (Chronic Oral)
- 1.250
- Fathead Minnow
- 3.560
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 218.490
- Hydration Free Energy
- -3.720
- Log(D) at pH=7.4
- 1.620
- Log(P)
- 2.39
- Log S
- -1.98
- Log(Vapor Pressure)
- -0.87
- Melting Point
- 52.6
- pKa Acid
- 9.61
- pKa Basic
- 8.43
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8648 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8648 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7752 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7752 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7683 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7683 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7564 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7564 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7544 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7544 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7371 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7371 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7332 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7332 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7272 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7272 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 2 | 0.7225 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 2 | 0.7225 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7202 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7202 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7180 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7180 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7177 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7177 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7102 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7102 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7032 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7032 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7016 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7016 |