ergovaline

Ergovaline is an ergopeptine and one of the ergot alkaloids. It is usually found in endophyte-infected species of grass like Tall fescue or Perennial Ryegrass. It is toxic to cattle feeding on infected grass, probably because it acts as a vasoconstrictor.

In the Vinony graph

Within Vinony's link graph, ergovaline is referenced by 219 other articles, and connects out to ergoline, Claviceps and lysergamides.

It is catalogued under topics including Chemical pages without DrugBank identifier, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.

Its subject is documented across 7 Wikipedia language editions.

Chemical data

Formula: C29H35N5O5
Molecular weight: 533.6 g/mol
IUPAC name: (6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
SMILES: CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
InChIKey: BGHDUTQZGWOQIA-VQSKNWBGSA-N
XLogP: 1.4
Polar surface area: 118 Å²
H-bond donors: 3
H-bond acceptors: 6
Formal charge: 0

via PubChem

Research

217 papers

Duration of ergovaline exposure influences serotonin-mediated vasoactivity of bovine mesenteric vasculature.Journal of animal science · 2023
Equine Mycotoxins.The Veterinary clinics of North America. Equine practice · 2024
Ruminal ergovaline and volatile fatty acid dynamics: Association with poor performance and a key growth regulator in steers grazing toxic tall fescue.Environmental toxicology and pharmacology · 2024
Influence of Prolonged Serotonin and Ergovaline Pre-Exposure on Vasoconstriction Ex Vivo.Toxins · 2021
Using On-Farm Monitoring of Ergovaline and Tall Fescue Composition for Horse Pasture Management.Toxins · 2021

via PubMed

Wikidata facts

Mass: 533.264

Show 5 more facts

chemical formula: C₂₉H₃₅N₅O₅
canonical SMILES: CC(C)C1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
isomeric SMILES: CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
found in taxon: Festuca rubra
Commons category: Ergovaline

Sources (2)

via Wikidata · CC0

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