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Beta-thujone
- Family: Plantae - Asteraceae
- 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-KHQFGBGNSA-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 |
Showing of synonyms
Beta-thujone
(-)-beta-thujone
(-)-Isothujone
Isothujone, (-)-
33766-30-2
0871SY94RA
UNII-0871SY94RA
(1R,4R,5S)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
(-)-.BETA.-THUJONE
CHEBI:50046
DTXSID50424914
Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1R,4R,5S)-
(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one (1R,4R,5S)-thujan-3-one
(1R,4R,5S)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
(1R,4R,5S)-1-Isopropyl-4-methylbicyclo(3.1.0)hexan-3-one
(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo(3.1.0)hexan-3-one
(1R,4R,5S)-4-methyl-1-propan-2-ylbicyclo(3.1.0)hexan-3-one
(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo(3.1.0)hexan-3-one (1R,4R,5S)-thujan-3-one
DTXCID80375748
(1s,4r,5s)-4-methyl-1-propan-2-ylbicyclo(3.1.0)hexan-3-one
(1s,4r,5s)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
Trans-thujone
L-Isothujone
(-)-cis-Thujone
(-)-3-Thujone
(1R,4R,5S)-thujan-3-one
LMPR0102120040
Q27121870
- 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]
Pubchem:
6553876
Cas:
33766-30-2
Zinc:
ZINC000001694437
Chebi:
50046
Nmrshiftdb2:
60031186
Metabolights:
MTBLC50046
Comptox:
DTXSID50424914
CPRiL:
70650
SMILES: C12C(C1)CC(=O)C2
Level: 0
Mol. Weight: 152.24 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.51
- 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
- -2.46
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.430
- Plasma Protein Binding
- 39.84
- 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
- 13.060
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.990
- 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
- 3.420
- 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
- 1.550
- Rat (Acute)
- 2.350
- 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
- 217.560
- Hydration Free Energy
- -3.730
- Log(D) at pH=7.4
- 1.620
- Log(P)
- 2.38
- Log S
- -2.01
- Log(Vapor Pressure)
- -0.88
- Melting Point
- 49.37
- pKa Acid
- 9.59
- pKa Basic
- 8.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8427 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8427 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7950 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7950 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7752 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7752 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7727 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7727 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7650 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7650 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7420 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7420 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7409 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7409 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7408 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7408 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7407 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7407 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7245 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7245 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7236 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7236 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7085 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7085 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7058 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7058 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7024 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7024 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7017 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7017 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7013 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7013 |