Structure via PubChem · Public domain (PubChem)
20-hydroxyecdysone
Sign in to saveAlso known as ecdysterone, crustecdysone, beta-ecdysterone, beta-ecdysone
20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. A phytoecdysteroid produced by and extracted from various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides, it is thought to be a plant defense against herbivory that disrupts the reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals (including humans) lack this recep
Chemical data
- Formula
- C27H44O7
- Molecular weight
- 480.6 g/mol
- IUPAC name
- (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- giardiasis, sarcopenia, COVID-19, muscular disease
via ChEMBL · EBI
Research
3,277 papers- 20-Hydroxyecdysone-responsive microRNAs of insects.RNA biology · 2020
- The potential of 20-hydroxyecdysone to accelerate termite baiting programs.Journal of economic entomology · 2025
- 20-Hydroxyecdysone inhibits inflammation via SIRT6-mediated NF-κB signaling in endothelial cells.Biochimica et biophysica acta. Molecular cell research · 2023
- [20-Hydroxyecdysone--plant adaptogen: an anabolic effect, possible use in sports nutrition].Voprosy pitaniia · 2013
- 20-hydroxyecdysone Upregulates Ecdysone Receptor (ECR) Gene to Promote Pupation in the Honeybee, Apis mellifera Ligustica.Integrative and comparative biology · 2023
via PubMed
Wikidata facts
- Mass
- 480.309
Show 4 more facts
- chemical formula
- C₂₇H₄₄O₇
- canonical SMILES
- CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
- isomeric SMILES
- C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O
- Commons category
- Hydroxyecdysone
via Wikidata · CC0
~4 min read
Article
8 sectionsContents
- Sources in arthropods
- Ecdysteroid activity in arthropods
- In humans and other mammals
- Use as research tool
- Use as supplement
- Drug development
- References
- External links
20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. A phytoecdysteroid produced by and extracted from various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides, it is thought to be a plant defense against herbivory that disrupts the reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals (including humans) lack this receptor, 20-hydroxyecdysone affects mammalian biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In mammals, it is hypothesized to bind to the estrogen receptor beta (ERβ) protein.
==Sources in arthropods== The primary sources of 20-hydroxyecdysone in larvae are the prothoracic gland, ring gland, gut, and fat bodies. These tissues convert dietary cholesterol into the mature forms of the hormone 20-hydroxyecdysone. For the most part, these glandular tissues are lost in the adult, with exception of the fat body, which is retained as a sheath of lipid tissue surrounding the brain and organs of the abdomen. In the adult female, the ovary is a substantial source of 20-hydroxyecdysone production. Adult males are left with, so far as is currently known, one source of 20-hydroxyecdysone, which is the fat body tissue. These hormone-producing tissues express the ecdysone receptor throughout development, possibly indicating a functional feedback mechanism.