CHEBI:10447 - β-thujaplicin

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ChEBI Name β-thujaplicin
ChEBI ID CHEBI:10447
ChEBI ASCII Name beta-thujaplicin
Definition A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:66015
Supplier Information ChemicalBook:CB8714323, eMolecules:1934753, ZINC000095911093
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Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.
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Formula C10H12O2
Net Charge 0
Average Mass 164.20110
Monoisotopic Mass 164.08373
InChI InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
InChIKey FUWUEFKEXZQKKA-UHFFFAOYSA-N
SMILES CC(C)c1cccc(=O)c(O)c1
Metabolite of Species Details
Chamaecyparis obtusa (NCBI:txid13415) See: PubMed
Thujopsis dolabrata (NCBI:txid13727) See: PubMed
Thuja plicata (NCBI:txid3316) See: PubMed
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antiplasmodial drug
An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing β-thujaplicin (CHEBI:10447) has parent hydride cyclohepta-1,3,5-triene (CHEBI:37519)
β-thujaplicin (CHEBI:10447) has role antibacterial agent (CHEBI:33282)
β-thujaplicin (CHEBI:10447) has role antifungal agent (CHEBI:35718)
β-thujaplicin (CHEBI:10447) has role antineoplastic agent (CHEBI:35610)
β-thujaplicin (CHEBI:10447) has role antiplasmodial drug (CHEBI:64915)
β-thujaplicin (CHEBI:10447) has role plant metabolite (CHEBI:76924)
β-thujaplicin (CHEBI:10447) is a cyclic ketone (CHEBI:3992)
β-thujaplicin (CHEBI:10447) is a enol (CHEBI:33823)
β-thujaplicin (CHEBI:10447) is a monoterpenoid (CHEBI:25409)
IUPAC Name
2-hydroxy-4-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
Synonyms Sources
2-hydroxy-4-isopropyl-cyclohepta2,4,6-trien-1-one ChEBI
4-Isopropyltropolone KEGG COMPOUND
beta-Thujaplicin KEGG COMPOUND
Hinokitiol KEGG COMPOUND
Manual Xrefs Databases
C00003062 KNApSAcK
C09904 KEGG COMPOUND
D04876 KEGG DRUG
Hinokitiol Wikipedia
HMDB0035213 HMDB
LSM-2835 LINCS
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Registry Numbers Types Sources
2045206 Reaxys Registry Number Reaxys
499-44-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
25 February 2016