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CHEBI:65415 - antroquinonol

ChEBI IDCHEBI:65415
ChEBI Nameantroquinonol
Stars
DefinitionAn 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.
Last Modified7 June 2017
DownloadsMolfile
FormulaC24H38O4
Net Charge0
Average Mass390.564
Monoisotopic Mass390.27701
SMILESCOC1=C(OC)[C@H](O)[C@H](C/C=C(\C)CC/C=C(\C)CCC=C(C)C)[C@@H](C)C1=O
InChIInChI=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
InChIKeyLJTSIMVOOOLKOL-FNRDIUJOSA-N
Species of MetaboliteComponentSourceComments
Taiwanofungus camphoratus (ncbitaxon:196114) mycelium (BTO:0001436) PubMed (17932820) Fermented Mycelium
Roles Classification
Biological Role:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:11257757Reaxys
Citations