CHEBI:66913 - ingenol mebutate

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ChEBI Name ingenol mebutate
ChEBI ID CHEBI:66913
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H34O6
Net Charge 0
Average Mass 430.53390
Monoisotopic Mass 430.236
InChI InChI=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
InChIKey VDJHFHXMUKFKET-UXMMOKKRSA-N
SMILES [H][C@@]12C=C(CO)[C@@H](O)[C@]3(O)[C@@H](OC(=O)C(\C)=C/C)C(C)=C[C@]3([C@H](C)C[C@]3([H])[C@@]1([H])C3(C)C)C2=O
Roles Classification
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 Sources
ingenol mebutate WHO MedNet
ingenoli mebutas WHO MedNet
mébutate d'ingénol WHO MedNet
mebutato de ingenol WHO MedNet
Synonyms Sources
3-Angeloylingenol ChemIDplus
3-Ingenyl angelate ChemIDplus
Ingenol 3-angelate ChemIDplus
PEP-005 ChemIDplus
Brand Name Source
Picato ChemIDplus
Database Links Databases
D09393 KEGG DRUG
Ingenol_mebutate Wikipedia
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Registry Numbers Types Sources
6452385 Reaxys Registry Number Reaxys
75567-37-2 CAS Registry Number ChemIDplus
75567-37-2 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017