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Antiviral API
- Arenavirus
- Cytomegalovirus (CMV)
- Dengue virus
- Endogenous Metabolite
- Enterovirus (EV)
- Epstein-Barr virus (EBV)
- Filovirus
- Flavivirus
- HCV Protease
- Hepatitis B Virus (HBV)
- Hepatitis C Virus (HCV)
- Herpes simplex Virus (HSV)
- HIF/HIF Prolyl-Hydroxylase
- HIV Integrase
- HIV Protease
- Human immunodeficiency Virus (HIV)
- Human papillomavirus (HPV)
- Influenza Virus
- Nipah virus
- Orthopoxvirus
- Others
- Rabies virus (RABV)
- Respiratory syncytial Virus (RSV)
- Reverse Transcriptases (RTs)
- SARS-CoV
- Tobacco mosaic virus (TMV)
- Vesicular stomatitis virus (VSV)
- Virus Protease
- West Nile virus
- Antiviral intermediates
Ilimaquinone
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. |
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 |