α-ergocryptine

Also known as 12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)ergotaman-3',6',18-trione, 12'-hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione

Ergocryptine is an ergopeptine and one of the ergoline alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine. Two isomers of ergocryptine exist, α-ergocryptine and β-ergocryptine. The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine. β-Ergocryptine was first identified in 1967 by Albert Hofmann. Ergot from different sources have different ratios of the two isomers.

In the Vinony graph

Within Vinony's link graph, α-ergocryptine is referenced by 223 other articles, and connects out to ergoline, Claviceps and lysergamides.

Vinony files it under Carboxamides, Chembox image size set and Chemical pages without DrugBank identifier.

Its subject is documented across 4 Wikipedia language editions.

Chemical data

Formula: C32H41N5O5
Molecular weight: 575.7 g/mol
IUPAC name: (6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-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[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
InChIKey: YDOTUXAWKBPQJW-NSLWYYNWSA-N
XLogP: 2.7
Polar surface area: 118 Å²
H-bond donors: 3
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

470 papers

Therapeutic potential of Xihuang Pill in colorectal cancer: Metabolomic and microbiome-driven approaches.Frontiers in pharmacology · 2024
Inhibition of lactation.Drugs · 1975
Ergocryptine and other ergot alkaloids stimulate the release of [3H]dopamine from rat striatal synaptosomes.Journal of animal science · 1999
An ergocryptine as a lactation inhibitor.Gynecologic investigation · 1974
Impacts of Cereal Ergot in Food Animal Production.Frontiers in veterinary science · 2016

via PubMed

Wikidata facts

Mass: 575.310769

Show 6 more facts

chemical formula: C₃₂H₄₁N₅O₅
canonical SMILES: CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
isomeric SMILES: CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O
subject has role: dopamine agonist
found in taxon: Festuca rubra
Commons category: Ergocryptine

Sources (2)

via Wikidata · CC0

~4 min read

Encyclopedic overview

3 sections

Contents

Biosynthesis
See also
References

==Biosynthesis== The biosynthetic pathways to ergocryptine starts with the prenylation of L-tryptophan in an SN1 fashion with dimethylallyl pyrophosphate (DMAPP). DMAPP is derived from mevalonic acid. This reaction is catalyzed by a prenyltransferase enzyme (Prenyltransferase 4-dimethylallyltryptophan synthase) named FgaPT2 in Aspergillus fumigatus. An X-ray structure of the prenyltransferase FgaPT2 and tryptophan has been reported, and used to propose a three step mechanism: (1) formation of allylic carbocation; (2) nucleophile attack of tryptophan on the carbocation; (3) deprotonation to restore aromaticity and generate the product, 4-dimethylallyltryptophan (DMAT). DMAT is then N-methylated at the amino of the tryptophan backbone with the EasF enzyme, named FgaMT in A. fumigatus. S-adenosylmethionine (SAM) being the methyl source.

Excerpted from Wikipedia’s “α-ergocryptine” article, available under the CC BY-SA 4.0 licence.