CHEBI:193028 - okaramine C

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ChEBI Name okaramine C
ChEBI ID CHEBI:193028
Definition An indole alkaloid isolated from Penicillium simplicissimum. It exhibits insecticidal activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C32H36N4O3
Net Charge 0
Average Mass 524.665
Monoisotopic Mass 524.27874
InChI InChI=1S/C32H36N4O3/c1-7-30(3,4)26-20(19-13-9-11-15-22(19)33-26)17-23-28(38)35-25(27(37)34-23)18-32(39)21-14-10-12-16-24(21)36(29(32)35)31(5,6)8-2/h7-16,23,25,29,33,39H,1-2,17-18H2,3-6H3,(H,34,37)/t23-,25-,29-,32-/m0/s1
InChIKey YWLAQSLUIQTZON-FQPFCCRUSA-N
SMILES [H][C@@]12C[C@]3(O)C4=CC=CC=C4N([C@]3([H])N1C(=O)[C@H](CC1=C(NC3=C1C=CC=C3)C(C)(C)C=C)NC2=O)C(C)(C)C=C
Metabolite of Species Details
Penicillium simplicissimum (NCBI:txid69488) of strain AHU 8402 See: DOI
Roles Classification
Biological Role(s): Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing okaramine C (CHEBI:193028) has role Penicillium metabolite (CHEBI:76964)
okaramine C (CHEBI:193028) has role insecticide (CHEBI:24852)
okaramine C (CHEBI:193028) is a indole alkaloid (CHEBI:38958)
okaramine C (CHEBI:193028) is a olefinic compound (CHEBI:78840)
okaramine C (CHEBI:193028) is a organic heterotetracyclic compound (CHEBI:38163)
okaramine C (CHEBI:193028) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(3S,5aR,10bS,11aS)-10b-hydroxy-6-(2-methylbut-3-en-2-yl)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
Synonym Source
(+)-okaramine C ChEBI
Manual Xref Database
C00026640 KNApSAcK
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Registry Number Type Source
142677-16-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15326519 PubMed citation Europe PMC
29168781 PubMed citation Europe PMC
32153648 PubMed citation Europe PMC
Last Modified
24 August 2022