ecdysone (CHEBI:16688)

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CHEBI:16688 - ecdysone

ChEBI ID	CHEBI:16688
ChEBI Name	ecdysone
Stars
Definition	A 6-oxo steroid that is 5β-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 22 and 25 respectively (the 2β, 3β, 22R stereoisomer). It is a steroid prohormone of the major insect moulting hormone 20-hydroxyecdysone.
Secondary ChEBI IDs	CHEBI:4741, CHEBI:14205, CHEBI:23889
Last Modified	8 April 2025
Downloads	Molfile

Formula	C27H44O6
Net Charge	0
Average Mass	464.643
Monoisotopic Mass	464.31379
SMILES	[H][C@@]12C[C@@H](O)[C@@H](O)C[C@]1(C)[C@@]1([H])CC[C@@]3(C)[C@@](O)(CC[C@]3([H])[C@H](C)[C@H](O)CCC(C)(C)O)C1=CC2=O
InChI	InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1
InChIKey	UPEZCKBFRMILAV-JMZLNJERSA-N

Wikipedia

Roles Classification

Biological Roles:

prohormone Any intra-glandular substance that acts as a precursor of a hormone, usually having minimal hormonal effect itself. Prohormones generally help in amplifying the effect of existing hormones.

hormone Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.

ChEBI Ontology

Outgoing Relation(s)
	ecdysone (CHEBI:16688) has parent hydride 5β-cholestane (CHEBI:35517)
	ecdysone (CHEBI:16688) has role prohormone (CHEBI:71212)
	ecdysone (CHEBI:16688) is a 14α-hydroxy steroid (CHEBI:36861)
	ecdysone (CHEBI:16688) is a 22-hydroxy steroid (CHEBI:36863)
	ecdysone (CHEBI:16688) is a 25-hydroxy steroid (CHEBI:36864)
	ecdysone (CHEBI:16688) is a 2β-hydroxy steroid (CHEBI:36859)
	ecdysone (CHEBI:16688) is a 3β-sterol (CHEBI:35348)
	ecdysone (CHEBI:16688) is a 6-oxo steroid (CHEBI:36883)
	ecdysone (CHEBI:16688) is a ecdysteroid (CHEBI:23897)
Incoming Relation(s)
	(24R)-11α,20,24-trihydroxyecdysone (CHEBI:18531) has functional parent ecdysone (CHEBI:16688)
	(25R)-11α,20,26-trihydroxyecdysone (CHEBI:18532) has functional parent ecdysone (CHEBI:16688)
	(25S)-11α,20,26-trihydroxyecdysone (CHEBI:46739) has functional parent ecdysone (CHEBI:16688)
	2-dehydroecdysone (CHEBI:19544) has functional parent ecdysone (CHEBI:16688)
	2-deoxyecdysone (CHEBI:19566) has functional parent ecdysone (CHEBI:16688)
	2,22,25-trideoxyecdysone (CHEBI:19290) has functional parent ecdysone (CHEBI:16688)
	20-hydroxyecdysone (CHEBI:16587) has functional parent ecdysone (CHEBI:16688)
	20,26-dihydroxyecdysone (CHEBI:19793) has functional parent ecdysone (CHEBI:16688)
	22-deoxy-20,21-dihydroxyecdysone (CHEBI:19804) has functional parent ecdysone (CHEBI:16688)
	22-deoxyecdysone (CHEBI:232767) has functional parent ecdysone (CHEBI:16688)
	25-deoxyecdysone (CHEBI:19814) has functional parent ecdysone (CHEBI:16688)
	3-dehydroecdysone (CHEBI:17058) has functional parent ecdysone (CHEBI:16688)
	ecdysone 25-O-D-glucopyranoside (CHEBI:23890) has functional parent ecdysone (CHEBI:16688)
	ecdysteroid ester (CHEBI:23895) has functional parent ecdysone (CHEBI:16688)

IUPAC Name
(2β,3β,5β,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one

Synonyms	Source
(22R)-2β,3β,14,22,25-pentahydroxy-5β-cholest-7-en-6-one	IUPAC
(22R)-2beta,3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-one	ChEBI
Ecdysone	KEGG COMPOUND

UniProt Name	Source
ecdysone	UniProt

Manual Xrefs	Databases
C00003651	KNApSAcK
C00477	KEGG COMPOUND
C00477	KEGG COMPOUND
Ecdysone	Wikipedia
LMST01010210	LIPID MAPS

Registry Numbers	Sources
Reaxys:2422986	Reaxys
CAS:3604-87-3	KEGG COMPOUND

Citations