CHEBI:66177 - scalusamide A

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ChEBI Name scalusamide A
ChEBI ID CHEBI:66177
Definition A pyrrolidine alkaloid that is a monocarboxylic acid amide obtained by the formal condensation of (8E)-2-methyl-3-oxodec-8-enoic acid with (2R)-pyrrolidin-2-ylmethanol. Isolated from the the cultured broth of the fungus Penicillium citrinum, it exhibits anti-fungal and antibacterial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H27NO3
Net Charge 0
Average Mass 281.39050
Monoisotopic Mass 281.19909
InChI InChI=1S/C16H27NO3/c1-3-4-5-6-7-10-15(19)13(2)16(20)17-11-8-9-14(17)12-18/h3-4,13-14,18H,5-12H2,1-2H3/b4-3+/t13?,14-/m1/s1
InChIKey LCDBRGPJMWXDGF-RTEOAJGCSA-N
SMILES C\C=C\CCCCC(=O)C(C)C(=O)N1CCC[C@@H]1CO
Metabolite of Species Details
Penicillium citrinum (NCBI:txid5077) of strain N055 See: PubMed
Roles Classification
Biological Role(s): Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing scalusamide A (CHEBI:66177) has role Penicillium metabolite (CHEBI:76964)
scalusamide A (CHEBI:66177) has role antibacterial agent (CHEBI:33282)
scalusamide A (CHEBI:66177) has role antifungal agent (CHEBI:35718)
scalusamide A (CHEBI:66177) is a monocarboxylic acid amide (CHEBI:29347)
scalusamide A (CHEBI:66177) is a primary alcohol (CHEBI:15734)
scalusamide A (CHEBI:66177) is a pyrrolidine alkaloid (CHEBI:26456)
IUPAC Name
(8E)-1-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyldec-8-ene-1,3-dione
Registry Number Type Source
15768979 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15730261 PubMed citation Europe PMC
Last Modified
13 January 2014
General Comment
2013-04-26 scalusamide A has been isolated as a mixture of epimers at C-7