Basic information
- CAS
5289-74-7- Standard SMILES
CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C- InChIKey
NKDFYOWSKOHCCO-YPVLXUMRSA-N- Molecular formula
- C27H44O7
- Average molar mass
- 480.6 g/mol
- Monoisotopic mass
- 480.30870375
Overview
20-hydroxyecdysone is an ecdysteroid that is ecdysone substituted by a hydroxy group at position 20. It has a role as an animal metabolite and a plant metabolite. It is an ecdysteroid, a phytoecdysteroid, a 3beta-sterol, a 20-hydroxy steroid, a 2beta-hydroxy steroid, a 14alpha-hydroxy steroid, a 22-hydroxy steroid and a 25-hydroxy steroid. It is functionally related to an ecdysone.
Names & identifiers
- Preferred name
- 20-Hydroxyecdysone
- IUPAC
- (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
- English name
- Hydroxyecdysone
- Molecular formula
- C27H44O7
- Molecular weight
- 480.64
Names & synonyms
20-HYDROXYECDYSONE5289-74-7Crustecdysonebeta-EcdysoneIsoinokosteroneCommisteroneCrustecdysonEcdysteronViticosteroneTHE-7Ekdistenbeta-ECDYSTERONE
Show more names
ECDYSTERONEβ-Ecdysteroneβ-EcdysoneB-ECDYSONEEcdysteroid
20-OH ecdysoneEcdystenBIO101779A7KPL0YBIO-101NSC-629484Bio 101DTXSID5040388
Database identifiers
- CAS
5289-74-7- PubChem CID
- 5459840
- DTXSID
DTXSID5040388- ChEMBL
CHEMBL224128- ChEBI
CHEBI:16587- UNII
- 779A7KPL0Y
- EC Number
- 811-097-1
- Nikkaji
- J13.425B
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 869
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Melting Point237.5 - 239.5 °C
Physical DescriptionSolid
Collision Cross Section
221.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
217.64 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 242 · 242-244 °C
- Boiling point
- 498.63 °C · 498.63°C (rough estimate)
- Density
- 1.076 · 1.0760 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- alcohol: soluble
- form
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 3.1% (1 of 32) of reports.
Warning
H400 (90.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 32 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAquatic Acute 1 (90.6%)
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- FZ8060000
- hs_code
- 29372900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H410
- Precautionary statements
- P501-P273-P391
Chemistry & industry
Pharmacology
Mechanism of Action
Sarconeos activates MAS receptors in muscle cells involved in the Renin-Angiotensin System which results in activation of the P13K/AKT/mTOR pathway. This activation increases protein production and helps preserve muscle mass and strength. In addition, Sarconeos also stimulates the AMPK/ACC pathway, which increases energy production and supports muscle strength and mobility.
Cellular LocationsExtracellular
Applications
Description20-Hydroxyecdysone (also known as Ecdysterone) is a hormone-like substance widely found in animals and plants, with a steroid ring at the core of its structure. It has the function of promoting arthropod molting and protecting plants from insects. Studies have shown that when used as a supplement, ecdysterone has a positive effect on human measurements and performance parameters, and is included in the World Anti-Doping Agency's banned list, but it has recently been found that there is a lack of scientific evidence to support WADA's ban on this substance.
Uses20-Hydroxyecdysone has been used:in Leibovitz′s dissecting medium for culturing sorting zone and neuropil-associated glia and antennal lobes of Manduca sextain Schneider′s medium to reproduce ex-vivo imaginal disc eversionas a supplement in Mcl8 medium for culturing Drosophila wing imaginal discsas an insect molting hormone
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
3 records
Compound notes
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