CHEBI:66636 - 14-norpseurotin A

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ChEBI Name 14-norpseurotin A
ChEBI ID CHEBI:66636
Definition An alkaloid that is the 14-nor derivative of pseurotin A. Isolated from Aspergillus sydowii, it exhibits antibacterial, antileishmanial and anticancer activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H23NO8
Net Charge 0
Average Mass 417.40920
Monoisotopic Mass 417.14237
InChI InChI=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
InChIKey FCGCMRDADMTJIM-LFDIKFNASA-N
SMILES CO[C@]1(NC(=O)[C@]2(OC([C@@H](O)[C@@H](O)\C=C/C)=C(C)C2=O)[C@H]1O)C(=O)c1ccccc1
Metabolite of Species Details
Aspergillus sydowii (NCBI:txid75750) of strain PFW1-13 See: PubMed
Roles Classification
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
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.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Xref Database
23329509 ChemSpider
View more database links
Registry Number Type Source
18842462 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18505285 PubMed citation Europe PMC
22474943 PubMed citation Europe PMC
Last Modified
27 October 2016