| Identification | Back Directory | [Name]
ECHINULIN | [CAS]
1859-87-6 | [Synonyms]
ECHINULIN
echinuline
2-(1,1-Dimethyl-2-propenyl)-5,7-diisopentenylcyclo(L-Trp-L-Ala-)
(3S,6S)-3-[[2-(1,1-dimethylallyl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-6-methyl-piperazine-2,5-quinone
(3S,6S)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
(3S,6S)-3-[[2-(1,1-Dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione
2,5-Piperazinedione,3-[[2-(1,1-dimethyl-2-propen-1-yl)-5,7-bis(3-methyl-2-buten-1-yl)-1H-indol-3-yl]methyl]-6-methyl-,(3S,6S)- | [Molecular Formula]
C29H39N3O2 | [MDL Number]
MFCD08274573 | [MOL File]
1859-87-6.mol | [Molecular Weight]
461.64 |
| Chemical Properties | Back Directory | [Melting point ]
242-243° | [alpha ]
D20 -26.0° (chloroform) | [Boiling point ]
695.3±55.0 °C(Predicted) | [density ]
1.068±0.06 g/cm3(Predicted) | [solubility ]
Methanol: soluble | [form ]
A solid | [pka]
13.05±0.60(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
Echinulin is a diketopiperazine metabolite found in fungi that, when administered to rabbits, at a dose of 10 mg/kg, leads to liver and lung damage.1 It has no activity at the δ, κ, or μ-opioid receptors or the cannabinoid CB1 and CB2 receptors.2 | [Uses]
Echinulin is a metabolite of diketopiperazine. | [Definition]
ChEBI: Echinulin is an indole alkaloid with formula C29H39N3O2. It is a fungal metabolite found in several Aspergillus species. It has a role as an Aspergillus metabolite, a marine metabolite and a plant metabolite. It is a member of indoles, a member of 2,5-diketopiperazines, an olefinic compound and an indole alkaloid. | [IC 50]
NF-κB | [References]
[1] MUSLIM ALI . Toxicity of echinulin from Aspergillus chevalieri in rabbits[J]. Toxicology letters, 1989, 48 3: Pages 235-241. DOI: 10.1016/0378-4274(89)90049-0
[2] JIANGTAO GAO. Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens[J]. Journal of Natural Products , 2011, 74 7: 1636-1639. DOI: 10.1021/np200147c |
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