اکدیسون

Also known as (22R)-2beta,3beta,14,22,25-pentahydroxy-5beta-cholest-7-en-6-one

Ecdysone is a prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. It is of steroidal structure. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. In Drosophila melanogaster, an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires. It causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Recen

Chemical data

Formula: C27H44O6
Molecular weight: 464.6 g/mol
IUPAC name: (2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
SMILES: C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)O)O
InChIKey: UPEZCKBFRMILAV-JMZLNJERSA-N
XLogP: 1.7
Polar surface area: 118 Å²
H-bond donors: 5
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

4,279 papers

Ecdysone controlled cell and tissue deletion.Cell death and differentiation · 2020
Ecdysone-mediated programmed cell death in Drosophila.The International journal of developmental biology · 2015
Regulation of ecdysone production in Drosophila by neuropeptides and peptide hormones.Open biology · 2021
An update on ecdysone signaling during insect oogenesis.Current opinion in insect science · 2019
Ecdysone receptors and their biological actions.Vitamins and hormones · 2000

via PubMed

Wikidata facts

Subclass of: sterol
Has part: carbon
Mass: 464.313789

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chemical formula: C₂₇H₄₄O₆
canonical SMILES: CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O
isomeric SMILES: C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)[C@@H](CCC(C)(C)O)O
discoverer or inventor: Adolf Butenandt
Commons category: Ecdysone

Sources (4)

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via Wikidata sitelinks · CC0