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Verruculogen information


Verruculogen
Names
Preferred IUPAC name
(5R,10S,10aR,14aS,15bS)-10,10a-Dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,12,13,14,14a,15b-octahydro-5H,15H-3,4-dioxa-5a,11a,15a-triazacycloocta[lm]indeno[5,6-b]fluorene-11,15(2H)-dione
Identifiers
CAS Number
  • 12771-72-1
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10405461
ECHA InfoCard 100.162.193 Edit this at Wikidata
KEGG
  • C20045
PubChem CID
  • 104862
CompTox Dashboard (EPA)
  • DTXSID30894030 Edit this at Wikidata
SMILES
  • CC(=CC1N2C3=C(C=CC(=C3)OC)C4=C2C(CC(OO1)(C)C)N5C(=O)C6CCCN6C(=O)C5(C4O)O)C
Properties
Chemical formula
C27H33N3O7
Molar mass 511.575 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Verruculogen is a mycotoxin produced by certain strains of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines.[1] It is an annulated analogue of cyclo(L-Trp-L-Pro) which belongs to the most abundant and structurally diverse class of tryptophan-proline 2,5-diketopiperazine natural products. It produces tremors in mice due to its neurotoxic properties. It also tested positive in a Salmonella/mammalian microsome assay and was shown to be genotoxic. It is a potent blocker of calcium-activated potassium channels.[2]

  1. ^ Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  2. ^ "Verruculogen from Penicillium verruculosum". sigmaaldrich.com. Retrieved 25 September 2023.

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Verruculogen

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Verruculogen is a mycotoxin produced by certain strains of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines. It is an annulated...

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Penicillium estinogenum

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estinogenum is an anamorph species of the genus of Penicillium which produces verruculogen. List of Penicillium species MycoBank Straininfo of Penicillium estinogenum...

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Foodborne illness

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These are fumitremorgen B, paxilline, penitrem A, verrucosidin, and verruculogen. Trichothecenes – sourced from Cephalosporium, Fusarium, Myrothecium...

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Penicillium raistrickii

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fungus in the genus Penicillium which produces griseofulvin, patulin and verruculogen. MycoBank Straininfo of Penicillium raistrickii Sarah De Saeger (2011)...

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Penicillium verruculosum

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Penicillium which was isolated from soil in the United States. It produces verruculogen, verrucosidin, verruculotoxin, decalpenic acid, dehydroaltenusin, cyciooctasulfur...

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List of biomolecules

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Uric acid – C5H4N4O3 Uridine Valine Valinomycin Vanabins Vasopressin Verruculogen Vitamins (in general) Vitamin A (retinol) Vitamin B Vitamin B1 (thiamine)...

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Fumitremorgin

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Gallagher, RT; Latch, GC (1977). "Production of the Tremorgenic Mycotoxins Verruculogen and Fumitremorgin B by Penicillium piscarium Westling". Applied and Environmental...

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