Structure via PubChem · Public domain (PubChem)
ecdysone
Sign in to saveAlso 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 Ų
- H-bond donors
- 5
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
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
- Mass
- 464.313789
Show 4 more facts
- 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
- Commons category
- Ecdysone
via Wikidata · CC0
~2 min read
Article
3 sectionsContents
- See also
- References
- External links
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. Recent findings in the laboratory of Chris Q. Doe have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells of the fruit fly.
Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. Some phytoecdysteroids may be bioactive in human contexts such as n ecdysteroid precursor from Stachyurus himalaicus, which exhibits cytotoxicity Ecdysones from insects have also exhibited antioxidant properties on lipid peroxidation.. Ecdysteroids are also found in the purport adaptogen Cordyceps militaris .