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CHEBI:5922 - ingenol

ChEBI IDCHEBI:5922
ChEBI Nameingenol
Stars
DefinitionA tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastereomer).
Last Modified28 July 2014
DownloadsMolfile
FormulaC20H28O5
Net Charge0
Average Mass348.439
Monoisotopic Mass348.19367
SMILES[H][C@@]12C[C@@H](C)[C@]34C=C(C)[C@H](O)[C@@]3(O)[C@H](O)C(CO)=C[C@H](C4=O)[C@]1([H])C2(C)C
InChIInChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-,19+,20-/m1/s1
InChIKeyVEBVPUXQAPLADL-POYOOMFHSA-N
ChEBI Ontology
Outgoing Relation(s)
ingenol (CHEBI:5922) is a cyclic terpene ketone (CHEBI:36130)
ingenol (CHEBI:5922) is a tetracyclic diterpenoid (CHEBI:52557)
Incoming Relation(s)
ingenol mebutate (CHEBI:66913) has functional parent ingenol (CHEBI:5922)
kansuiphorin A (CHEBI:66138) has functional parent ingenol (CHEBI:5922)
kansuiphorin B (CHEBI:66139) has functional parent ingenol (CHEBI:5922)
IUPAC Name 
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one
Manual XrefsDatabases
C09112KEGG COMPOUND
C00003439KNApSAcK
Registry NumbersSources
Reaxys:2017351Reaxys
CAS:30220-46-3KEGG COMPOUND
CAS:30220-46-3ChemIDplus