Antroquinonol
(4R,5R,6R)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]cyclohex-2-en-1-one
Molecular Identity
Antroquinonol
(4R,5R,6R)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]cyclohex-2-en-1-one
PubChem CID: 24875259
Antroquinonol is 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. It has a role as an antineoplastic agent and a fungal metabolite. It is a secondary alcohol, an enol ether and an enone.
2D Structure
Properties
C24H38O4
Molecular Formula
390.60
Molecular Weight
g/mol
390.2770
Exact Mass
Da
5.8
XLogP
Above Lipinski threshold
55.8
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
4
H-Bond Acceptors
648
Complexity
SMILES
Canonical SMILES
SMILES: CC1C(C(C(=C(C1=O)OC)OC)O)CC=C(C)CCC=C(C)CCC=C(C)CIsomeric SMILES
SMILES: C[C@@H]1[C@H]([C@H](C(=C(C1=O)OC)OC)O)C/C=C(\C)/CC/C=C(\C)/CCC=C(C)CSynonyms(20)
antroquinonol1010081-09-0HocenaAntroquinonol A(+)-Antroquinonol A(+)-AntroquinonolAX9P92T7JZJ3.387.174KCHEBI:65415(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(4R,5R,6R)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]cyclohex-2-en-1-one(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-one2-Cyclohexen-1-one, 4-hydroxy-2,3-dimethoxy-6-methyl-5-((2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)-, (4R,5R,6R)-(4R)-2,3-Dimethoxy-4alpha-hydroxy-5alpha-((2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl)-6beta-methyl-2-cyclohexene-1-one(4R,5R,6R)-4-hydroxy-2,3-dimethoxy-6-methyl-5-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)cyclohex-2-en-1-one
Data from PubChem (NCBI)
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