CHEBI:65415 - antroquinonol

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ChEBI Name antroquinonol
ChEBI ID CHEBI:65415
Definition An enone that is cyclohex-2-en-1-one substituted by a hydroxy group at position 4, methoxy groups at positions 2 and 3, a methyl group at position 6 and a (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl group at position 5 (the 4R,5R,6R stereoisomer). It is isolated from the solid-state fermented mycelium of the fungus Antrodia camphorata and has been found to exhibit potent cytotoxicity against a number of human cancer cell lines. However, a synthesis-enabled biological re-examination published in 2016, revealed minimal in vitro and in vivo antitumour activity in preclinical models.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H38O4
Net Charge 0
Average Mass 390.55610
Monoisotopic Mass 390.27701
InChI InChI=1S/C24H38O4/c1-16(2)10-8-11-17(3)12-9-13-18(4)14-15-20-19(5)21(25)23(27-6)24(28-7)22(20)26/h10,12,14,19-20,22,26H,8-9,11,13,15H2,1-7H3/b17-12+,18-14+/t19-,20-,22-/m1/s1
InChIKey LJTSIMVOOOLKOL-FNRDIUJOSA-N
SMILES COC1=C(OC)C(=O)[C@H](C)[C@@H](C\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H]1O
Metabolite of Species Details
Taiwanofungus camphoratus (NCBI:txid196114) Found in mycelium (BTO:0001436). Fermented Mycelium See: PubMed
Roles Classification
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing antroquinonol (CHEBI:65415) has role antineoplastic agent (CHEBI:35610)
antroquinonol (CHEBI:65415) has role fungal metabolite (CHEBI:76946)
antroquinonol (CHEBI:65415) is a enol ether (CHEBI:47985)
antroquinonol (CHEBI:65415) is a enone (CHEBI:51689)
antroquinonol (CHEBI:65415) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(4R,5R,6R)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]cyclohex-2-en-1-one
Registry Number Type Source
11257757 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17932820 PubMed citation Europe PMC
19723512 PubMed citation Europe PMC
21540101 PubMed citation Europe PMC
21840189 PubMed citation Europe PMC
21905011 PubMed citation Europe PMC
25679542 PubMed citation Europe PMC
25875221 PubMed citation Europe PMC
26039178 PubMed citation Europe PMC
27163023 PubMed citation Europe PMC
27997180 PubMed citation Europe PMC
Last Modified
07 June 2017