Alpha-Ecdysone

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Alpha-Ecdysone
Systematic (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
Identifiers
CAS number	3604-87-3
ATC code	?
PubChem	19212
Chemical data
Formula	C27H44O6
Mol. mass	464.63
SMILES	eMolecules & PubChem
Synonyms	Ecdysone
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

A steroid hormone that regulates the processes of MOLTING or ecdysis in insects.

Ecdysone is a steroidal prohormone of the major insect molting hormone 20-hydroxyecdysone, which is secreted from the prothoracic glands. 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, and it causes chromosome puffs (sites of high expression) to form. Ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. These phytoecdysteroids have medicinal valueTemplate:Fact and are part of herbal adaptogenic remedies like Cordyceps. A pesticide sold with the name MIMIC has ecdysteroid activity, although its chemical structure has little resemblance to the ecdysteroids.

General Properties

*Molecular Weight

464.63

*Molecular Formula

C₂₇H₄₄O₆

*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

*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

External Links

• [1]Pubchem
• [2]KEGG Compound