CHEBI:16688 - ecdysone

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ChEBI Name ecdysone
ChEBI ID CHEBI:16688
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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4741, CHEBI:14205, CHEBI:23889
Supplier Information ChemicalBook:CB8113524, eMolecules:508943, eMolecules:36516801, Selleckchem:Ecdysone, ZINC000004228274
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Formula C27H44O6
Net Charge 0
Average Mass 464.63466
Monoisotopic Mass 464.31379
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
SMILES [H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](O)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@H](O)CCC(C)(C)O
Roles Classification
Biological Role(s): 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.
(via ecdysteroid )
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ChEBI Ontology
Outgoing 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 2β-hydroxy steroid (CHEBI:36859)
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 3β-sterol (CHEBI:35348)
ecdysone (CHEBI:16688) is a 6-oxo steroid (CHEBI:36883)
ecdysone (CHEBI:16688) is a ecdysteroid (CHEBI:23897)
Incoming (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)
2,22,25-trideoxyecdysone (CHEBI:19290) 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)
20,26-dihydroxyecdysone (CHEBI:19793) has functional parent ecdysone (CHEBI:16688)
20-hydroxyecdysone (CHEBI:16587) 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 Sources
(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
ecdysone UniProt
Manual Xrefs Databases
C00003651 KNApSAcK
C00477 KEGG COMPOUND
Ecdysone Wikipedia
LMST01010210 LIPID MAPS
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Registry Numbers Types Sources
2422986 Reaxys Registry Number Reaxys
3604-87-3 CAS Registry Number KEGG COMPOUND
Citations Waiting for Citations Types Sources
19342482 PubMed citation Europe PMC
22310011 PubMed citation Europe PMC
22828514 PubMed citation Europe PMC
23017214 PubMed citation Europe PMC
23072462 PubMed citation Europe PMC
Last Modified
20 April 2015