Ilimaquinone

• CAT Number: R064979
• CAS Number: 71678-03-0
• Molecular Formula: C22H30O4
• Molecular Weight: 358.478
• Purity: ≥95%
• Synonyms: 3-[[(1R,2S,4aS,8aS)-decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione
• Storage: -20°C
• IUPAC Name: 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
• InChI: InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18+,21+,22+/m0/s1
• InChIKey: JJWITJNSXCXULM-YVUMSICPSA-N
• SMILES: CC1CCC2(C(C1(C)CC3=C(C(=O)C=C(C3=O)OC)O)CCCC2=C)C

Ilimaquinone is a natural sesquiterpene quinone that has antimicrobial, anti-<wbr></wbr>HIV, anti-<wbr></wbr>mitotic, and anti-<wbr></wbr>inflammatory properties. In mammalian cells, 25 µM ilimaquinone reversibly induces vesiculation of Golgi membranes, blocking the secretory pathway. It inhibits the conversion of S-<wbr></wbr>adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase (IC50 = 40 µM). Ilimaquinone also inhibits DNA polymerase β and dual specificity phosphatase Cdc25B (IC50 = 45.2 and 92 µM, respectively) and, at 10 µM, activates gene expression through hypoxia-<wbr></wbr>inducible factor-<wbr></wbr>1.

Reference

1.Radeke, H.S.,Digits, C.A.,Casaubon, R.L., et al. Interactions of (−)-ilimaquinone with methylation enzymes: Implications for vesicular-mediated secretion. Chemistry & Biology 6(9), 639-647 (1999).