EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66177 - scalusamide A

ChEBI IDCHEBI:66177
ChEBI Namescalusamide A
Stars
DefinitionA 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.
Last Modified13 January 2014
DownloadsMolfile
FormulaC16H27NO3
Net Charge0
Average Mass281.396
Monoisotopic Mass281.19909
SMILESC/C=C/CCCCC(=O)C(C)C(=O)N1CCC[C@@H]1CO
InChIInChI=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
InChIKeyLCDBRGPJMWXDGF-RTEOAJGCSA-N
Species of MetaboliteComponentSourceComments
Penicillium citrinum (ncbitaxon:5077) - PubMed (15730261) Strain: N055
Roles Classification
Biological Roles:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
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.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:15768979Reaxys
Citations