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| Names | |
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| Preferred IUPAC name
(3Z,6S)-3-{[5-(2-Methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}-6-(propan-2-yl)piperazine-2,5-dione | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C16H22N4O2 | |
| Molar mass | 302.378 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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(−)-Aurantiamine is a blue fluorescence metabolite produced by the fungus Penicillium aurantiogriseum, the most common fungi found in cereals.[2] (−)-Aurantiamine belongs to a class of naturally occurring 2,5-diketopiperazines featuring a dehydrohistidine residue that exhibit important biological activities, such as anti-cancer or neurotoxic effects.[3] It is the isopropyl analog of the microtubule binding agent (−)-phenylahistin but is 40 times less active than the latter on P388 cell proliferation.[4] The total asymmetric synthesis of (−)-aurantiamine has been described.[5]
