Page last updated: 2024-11-06

alpha-thujaplicin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Alpha-thujaplicin, also known as hinokitiol, is a tropolone derivative found in the heartwood of several coniferous trees, including Western red cedar (Thuja plicata) and Japanese cypress (Chamaecyparis obtusa). It exhibits a wide range of biological activities, including antibacterial, antifungal, antiviral, antioxidant, and anti-inflammatory properties. Alpha-thujaplicin has been shown to inhibit the growth of various bacteria, including Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. It also possesses antifungal activity against Candida albicans and Aspergillus niger. Additionally, alpha-thujaplicin has demonstrated antiviral activity against influenza virus and herpes simplex virus. The compound's antioxidant properties are attributed to its ability to scavenge free radicals, while its anti-inflammatory effects are thought to be mediated through the inhibition of pro-inflammatory cytokines. Research into alpha-thujaplicin is ongoing to explore its potential as a therapeutic agent for various diseases, including infections, inflammation, and cancer. Its natural origin, wide range of bioactivities, and low toxicity make it an attractive candidate for the development of novel drugs.'

alpha-thujaplicin: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID80297
CHEMBL ID1275969
SCHEMBL ID355645
MeSH IDM0554911

Synonyms (20)

Synonym
6tu33pgy8a ,
1946-74-3
unii-6tu33pgy8a
alpha-thujaplicin
2,4,6-cycloheptatrien-1-one, 2-hydroxy-3-(1-methylethyl)-
.alpha.-thujaplicin
2-hydroxy-3-isopropyl-cyclohepta-2,4,6-trien-1-one
2-hydroxy-3-propan-2-ylcyclohepta-2,4,6-trien-1-one
2-hydroxy-3-isopropyl-2,4,6-cycloheptatrien-1-one
CHEMBL1275969 ,
bdbm50330793
SCHEMBL355645
thujaplicin
TUFYVOCKVJOUIR-UHFFFAOYSA-N
3it ,
DTXSID70173098
AKOS025402371
AC-8489
3-isopropyltropolone
2-hydroxy-3-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)9.53000.03403.987110.0000AID1167964; AID1611942; AID537590
Polyphenol oxidase 2Agaricus bisporusKi3.30000.00063.28838.8900AID537591
TyrosinaseHomo sapiens (human)IC50 (µMol)1,000.00000.02304.459310.0000AID1167965
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
melanin biosynthetic process from tyrosineTyrosinaseHomo sapiens (human)
eye pigment biosynthetic processTyrosinaseHomo sapiens (human)
visual perceptionTyrosinaseHomo sapiens (human)
cell population proliferationTyrosinaseHomo sapiens (human)
response to UVTyrosinaseHomo sapiens (human)
response to blue lightTyrosinaseHomo sapiens (human)
response to vitamin DTyrosinaseHomo sapiens (human)
melanin biosynthetic processTyrosinaseHomo sapiens (human)
thymus developmentTyrosinaseHomo sapiens (human)
response to cAMPTyrosinaseHomo sapiens (human)
pigmentationTyrosinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
tyrosinase activityTyrosinaseHomo sapiens (human)
copper ion bindingTyrosinaseHomo sapiens (human)
protein bindingTyrosinaseHomo sapiens (human)
identical protein bindingTyrosinaseHomo sapiens (human)
protein homodimerization activityTyrosinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
cytoplasmTyrosinaseHomo sapiens (human)
lysosomeTyrosinaseHomo sapiens (human)
Golgi-associated vesicleTyrosinaseHomo sapiens (human)
melanosome membraneTyrosinaseHomo sapiens (human)
melanosomeTyrosinaseHomo sapiens (human)
intracellular membrane-bounded organelleTyrosinaseHomo sapiens (human)
perinuclear region of cytoplasmTyrosinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (49)

Assay IDTitleYearJournalArticle
AID1103251Acaricidal activity against Dermatophagoides farinae after 24 hr2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID537591Competitive inhibition of mushroom tyrosinase after 15 mins by Lineweaver-Burke plot analysis2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.
AID1232069Inhibition of Escherichia coli ribonuclease H2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1103250Acaricidal activity against Tyrophagus putrescentiae at high concentration2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103256Acaricidal activity against Dermatophagoides farinae assessed as mortality at 0.01 g/m'2 after 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1167967Ratio of kojic acid IC50 to compound IC50 for human tyrosinase2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.
AID1103289Antifungal activity against Thanatephorus cucumeris IFO 30455 after 15 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103284Antifungal activity against Colletotrichum lagenaria after 15 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103248Growth inhibition of Mus musculus (mouse) P388 cells at >1.25 ug/ml after 24 hr by MTT assay2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1611942Inhibition of mushroom tyrosinase2018Journal of medicinal chemistry, 09-13, Volume: 61, Issue:17
Inhibitors of Melanogenesis: An Updated Review.
AID1167969Ratio of IC50 for tyrosinase in human G-361 cells to IC50 for mushroom tyrosinase2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.
AID1103283Antifungal activity against Colletotrichum orbiculare MAFF 306518 after 15 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1232067Inhibition of HIV1 reverse transcriptase RNase H2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1103285Antifungal activity against Phomopsis obscurans MAFF 744018 after 15 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103287Antifungal activity against Fusarium solani IFO 9955 after 15 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID537592Inhibition of mushroom tyrosinase at 3 uM after 15 mins by Michaelis-Menten constant analysis2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.
AID1103278Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.1 g/m'2 at 48 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103275Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.04 g/m'2 at 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103245Growth inhibition of Mus musculus (mouse) P388 cells at >1.25 ug/ml after 48 hr by MTT assay2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID537593Inhibition of mushroom tyrosinase at 6 uM after 15 mins by Michaelis-Menten constant analysis2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.
AID1103272Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.02 g/m'2 at 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103273Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.03 g/m'2 at 48 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103279Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.05 g/m'2 at 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103286Antifungal activity against Botryotinia fuckeliana IFO 30915 after 15 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103276Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.04 g/m'2 at 48 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103288Antifungal activity against Pythium aphanidermatum IFO 32440 after 15 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103246Growth inhibition of Mus musculus (mouse) P388 cells at 0.63 ug/ml after 48 hr by MTT assay2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103269Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.01 g/m'2 at 48 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103274Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.03 g/m'2 at 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103281Antibacterial activity against Legionella pneumophila SG 3 after 7 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103252Insecticidal activity against Reticulitermes speratus at 48 hr2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103271Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.01 g/m'2 at 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1167965Competitive inhibition of tyrosinase in human G-361 cells incubated for 10 mins measured for 2 hrs by MBTH-based spectrophotometry2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.
AID1611944Selectivity ratio of IC50 for human tyrosinase to IC50 for mushroom tyrosinase2018Journal of medicinal chemistry, 09-13, Volume: 61, Issue:17
Inhibitors of Melanogenesis: An Updated Review.
AID1167964Non-competitive inhibition of mushroom tyrosinase2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.
AID1103259Acaricidal activity against Dermatophagoides farinae assessed as mortality at 1 g/m'2 after 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103277Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.05 g/m'2 at 48 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1167966Inhibition of tyrosinase in human G-361 cells at >200 uM incubated for 10 mins measured for 2 hrs by MBTH-based spectrophotometry2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.
AID1103282Antibacterial activity against Legionella pneumophila SG 1 after 7 days by agar dilution method2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103249Growth inhibition of Mus musculus (mouse) P388 cells after 24 to 48 hr by MTT assay2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103247Growth inhibition of Mus musculus (mouse) P388 cells at 0.63 ug/ml after 24 hr by MTT assay2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1232068Inhibition of HIV2 reverse transcriptase RNase H2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID537590Inhibition of mushroom tyrosinase after 15 mins2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.
AID1103244Toxicity against ip dosed Mus musculus Slc:ddY (mouse) after 8 days2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1232070Inhibition of human ribonuclease H2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1103257Acaricidal activity against Dermatophagoides farinae assessed as mortality at 0.1 g/m'2 after 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103270Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.02 g/m'2 at 48 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103258Acaricidal activity against Dermatophagoides farinae assessed as mortality at 0.5 g/m'2 after 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
AID1103280Insecticidal activity against Reticulitermes speratus assessed as mortality at 0.1 g/m'2 at 24 hr relative to control2004Biological & pharmaceutical bulletin, Jun, Volume: 27, Issue:6
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (16.67)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's4 (66.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.52

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.52 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]