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Ilimaquinone

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Category Human immunodeficiency Virus (HIV)
CAS 71678-03-0
Description Ilimaquinone is a marine sponge metabolite with antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties. Ilimaquinone significantly enhanced TRAIL-induced apoptosis in HCT 116 cells and sensitized colon cancer cells to TRAIL-induced apoptosis through increased caspase-8, -3 activation, PARP cleavage, and DNA damage. Ilimaquinone also reduced the cell survival proteins Bcl2 and Bcl-xL, while strongly up-regulating death receptor (DR) 4 and DR5 expression.
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Product Information

Synonyms ilimaquinone; 71678-03-0; Illimaquinone; UNII-5U0WAN3N8Q5U0WAN3N8Q
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
Molecular Weight 358.5
Molecular Formula C22H30O4
Canonical SMILES CC1CCC2(C(C1(C)CC3=C(C(=O)C=C(C3=O)OC)O)CCCC2=C)C
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
Boiling Point 478.4±45.0 °C at 760 mmHg
Flash Point 159.9±22.2 °C
Purity ≥98%
Density 1.1±0.1 g/cm3
Solubility In vitro:
10 mM in DMSO
Appearance Solid Powder
Storage Powder:
-20°C: 3 years
4°C: 2 years
In solvent:
-80°C: 6 months
-20°C: 1 month
Complexity 728
Exact Mass 358.21440943
Index Of Refraction 1.549
In Vitro Ilimaquinone induces a concentration-dependent anti-proliferative effect in several types of cancer cell lines, including prostate cancer PC-3 and LNCaP, non-small cell lung cancer A549 and hepatocellular carcinoma Hep3B cells. Ilimaquinone (0.3-30 μM; 48 hours) inhibits the proliferation of PC-3 cells, DU145, LNCaP, MG63, A549, Hep3B cells with GI50s of 2.6 μM, 5.8, 4.6, 4.9, 4.1, 12.0μM, respectively.
PSA 63.60000
Target HIV; Bacterial
Vapor Pressure 0.0±2.7 mmHg at 25°C
XLogP3-AA 5.1

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