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CHEBI:66913 - ingenol mebutate

Default Structure
ChEBI IDCHEBI:66913
ChEBI Nameingenol mebutate
Stars
DefinitionA tetracyclic diterpenoid ester obtained by formal condensation of the carboxy group of (2Z)-2-methylbut-2-enoic (angelic) acid with the 3-hydroxy group of ingenol. Used for the topical treatment of actinic keratosis.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC25H34O6
Net Charge0
Average Mass430.541
Monoisotopic Mass430.23554
SMILES[H][C@@]12C(C)(C)[C@]1([H])C[C@@H](C)[C@]13C=C(C)[C@H](OC(=O)/C(C)=C\C)[C@@]1(O)[C@H](O)C(CO)=C[C@@]2([H])C3=O
InChIInChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16-,17-,18+,19-,21+,24+,25+/m1/s1
InChIKeyVDJHFHXMUKFKET-UXMMOKKRSA-N
Wikipedia
Roles Classification
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
ingenol mebutate (CHEBI:66913) has functional parent angelic acid (CHEBI:36431)
ingenol mebutate (CHEBI:66913) has functional parent ingenol (CHEBI:5922)
ingenol mebutate (CHEBI:66913) has role antineoplastic agent (CHEBI:35610)
ingenol mebutate (CHEBI:66913) is a carboxylic ester (CHEBI:33308)
ingenol mebutate (CHEBI:66913) is a cyclic terpene ketone (CHEBI:36130)
ingenol mebutate (CHEBI:66913) is a tetracyclic diterpenoid (CHEBI:52557)
IUPAC Name 
(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[E][10]annulen-6-yl (2Z)-2-methylbut-2-enoate
INNs  Source
ingenoli mebutasWHO MedNet
ingenol mebutateWHO MedNet
mébutate d'ingénolWHO MedNet
mebutato de ingenolWHO MedNet
Synonyms  Source
3-AngeloylingenolChemIDplus
3-Ingenyl angelateChemIDplus
Ingenol 3-angelateChemIDplus
PEP-005ChemIDplus
Brand Name  Source
PicatoChemIDplus
Manual XrefsDatabases
D09393KEGG DRUG
Ingenol_mebutateWikipedia
Registry NumbersSources
Reaxys:6452385Reaxys
CAS:75567-37-2ChemIDplus
CAS:75567-37-2KEGG DRUG
Citations