CHEBI:195528 - NPD6433

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ChEBI Name NPD6433
ChEBI ID CHEBI:195528
Definition An indolyl carboxylate ester that is 1H-indole substituted by methoxycarbonyl and (E)-(8-oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(4H)-yl)diazenyl groups at positions 2 and 3, respectively. It targets the enoyl reductase domain of fungal fatty acid synthase, exhibits broad-spectrum antifungal activity, is bioactive against the filamentous mold, Aspergillus fumigatus and has minimal mammalian cytotoxicity.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Rob Nash
Supplier Information
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Formula C21H21N5O3
Net Charge 0
Average Mass 391.431
Monoisotopic Mass 391.16444
InChI InChI=1S/C21H21N5O3/c1-29-21(28)20-19(15-5-2-3-6-16(15)22-20)23-24-25-10-13-9-14(12-25)17-7-4-8-18(27)26(17)11-13/h2-8,13-14,22H,9-12H2,1H3/b24-23+
InChIKey IXWNPEOFLGJGLY-WCWDXBQESA-N
SMILES COC(=O)C1=C(\N=N\N2CC3C[C@H](C2)C2=CC=CC(=O)N2C3)C2=C(N1)C=CC=C2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 2.3.1.85 (fatty acid synthase) inhibitor
An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of fatty acid synthase (EC 2.3.1.85), a multi-enzyme protein involved in fatty acid synthesis.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing NPD6433 (CHEBI:195528) has role antifungal agent (CHEBI:35718)
NPD6433 (CHEBI:195528) has role EC 2.3.1.85 (fatty acid synthase) inhibitor (CHEBI:71476)
NPD6433 (CHEBI:195528) is a bridged compound (CHEBI:35990)
NPD6433 (CHEBI:195528) is a indolyl carboxylate ester (CHEBI:46939)
NPD6433 (CHEBI:195528) is a methyl ester (CHEBI:25248)
NPD6433 (CHEBI:195528) is a organic heterocyclic compound (CHEBI:24532)
NPD6433 (CHEBI:195528) is a tertiary amino compound (CHEBI:50996)
NPD6433 (CHEBI:195528) is a triazene derivative (CHEBI:72573)
IUPAC Name
methyl 3-[(E)-(8-oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(4H)-yl)diazenyl]-1H-indole-2-carboxylate
Citation Waiting for Citations Type Source
37369212 PubMed citation SUBMITTER
Last Modified
09 August 2023