CHEBI:66636 - 14-norpseurotin A

ChEBI IDCHEBI:66636
ChEBI Name14-norpseurotin A
Stars
DefinitionAn alkaloid that is the 14-nor derivative of pseurotin A. Isolated from Aspergillus sydowii, it exhibits antibacterial, antileishmanial and anticancer activities.
Last Modified27 October 2016
DownloadsMolfile
FormulaC21H23NO8
Net Charge0
Average Mass417.414
Monoisotopic Mass417.14237
SMILESC/C=C\[C@H](O)[C@H](O)C1=C(C)C(=O)[C@]2(O1)C(=O)N[C@@](OC)(C(=O)c1ccccc1)[C@@H]2O
InChIInChI=1S/C21H23NO8/c1-4-8-13(23)14(24)15-11(2)16(25)20(30-15)18(27)21(29-3,22-19(20)28)17(26)12-9-6-5-7-10-12/h4-10,13-14,18,23-24,27H,1-3H3,(H,22,28)/b8-4-/t13-,14-,18+,20+,21+/m0/s1
InChIKeyFCGCMRDADMTJIM-LFDIKFNASA-N
Species of MetaboliteComponentSourceComments
Aspergillus sydowii (ncbitaxon:75750) - PubMed (18505285) Strain: PFW1-13
Roles Classification
Biological Roles:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
14-norpseurotin A (CHEBI:66636) has functional parent pseurotin A (CHEBI:64535)
14-norpseurotin A (CHEBI:66636) has role Aspergillus metabolite (CHEBI:76956)
14-norpseurotin A (CHEBI:66636) has role antibacterial agent (CHEBI:33282)
14-norpseurotin A (CHEBI:66636) has role antileishmanial agent (CHEBI:70868)
14-norpseurotin A (CHEBI:66636) has role antineoplastic agent (CHEBI:35610)
14-norpseurotin A (CHEBI:66636) is a alkaloid (CHEBI:22315)
14-norpseurotin A (CHEBI:66636) is a azaspiro compound (CHEBI:35624)
14-norpseurotin A (CHEBI:66636) is a lactam (CHEBI:24995)
14-norpseurotin A (CHEBI:66636) is a oxaspiro compound (CHEBI:37948)
14-norpseurotin A (CHEBI:66636) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxypent-3-en-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Manual XrefsDatabases
23329509ChemSpider
Registry NumbersSources
Reaxys:18842462Reaxys
Citations