CHEBI:63459 - shionone

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name shionone
ChEBI ID CHEBI:63459
Definition A tetracyclic triterpenoid that is perhydrochrysene which is substituted by methyl groups at positions 1, 4bβ, 6aα, 8β, 10aβ and 12a positions, by a 4-methylpent-3-enyl group at the 8α position, and with an oxo group at position 2.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
Download Molfile XML SDF
Formula C30H50O
Net Charge 0
Average Mass 426.71740
Monoisotopic Mass 426.38617
InChI InChI=1S/C30H50O/c1-21(2)10-9-14-26(4)16-19-30(8)25-13-15-28(6)22(3)23(31)11-12-24(28)29(25,7)18-17-27(30,5)20-26/h10,22,24-25H,9,11-20H2,1-8H3/t22-,24+,25-,26+,27-,28+,29-,30+/m0/s1
InChIKey HXPXUNQUXCHJLL-LZQQOHPBSA-N
SMILES [H][C@@]12CCC(=O)[C@H](C)[C@@]1(C)CC[C@@]1([H])[C@@]2(C)CC[C@@]2(C)C[C@](C)(CCC=C(C)C)CC[C@]12C
ChEBI Ontology
Outgoing shionone (CHEBI:63459) is a cyclic terpene ketone (CHEBI:36130)
shionone (CHEBI:63459) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name
(1R,4aS,4bS,6aS,8R,10aR,10bS,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methylpent-3-en-1-yl)hexadecahydrochrysen-2(1H)-one
Synonyms Sources
D:A-friedo-18,19-secolup-19-en-3-one ChemIDplus
shionone UniProt
Manual Xref Database
C17966 KEGG COMPOUND
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Registry Number Type Source
10376-48-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14191440 PubMed citation Europe PMC
21377465 PubMed citation SUBMITTER
Last Modified
28 July 2014
General Comment
2011-12-22 Needed for the new IUBMB reaction (3S)-2,3-epoxy-2,3-dihydrosqualene = shionone.