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CHEBI:16688 - ecdysone

ChEBI IDCHEBI:16688
ChEBI Nameecdysone
Stars
DefinitionA 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 IDsCHEBI:4741, CHEBI:14205, CHEBI:23889
Last Modified8 April 2025
DownloadsMolfile
FormulaC27H44O6
Net Charge0
Average Mass464.643
Monoisotopic Mass464.31379
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
InChIInChI=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
InChIKeyUPEZCKBFRMILAV-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
EcdysoneKEGG COMPOUND
(22R)-2beta,3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-oneChEBI
(22R)-2β,3β,14,22,25-pentahydroxy-5β-cholest-7-en-6-oneIUPAC
UniProt Name  Source
ecdysoneUniProt
Manual XrefsDatabases
C00477KEGG COMPOUND
C00477KEGG COMPOUND
EcdysoneWikipedia
LMST01010210LIPID MAPS
C00003651KNApSAcK
Registry NumbersSources
Reaxys:2422986Reaxys
CAS:3604-87-3KEGG COMPOUND
Citations