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CHEBI:195528 - NPD6433

ChEBI IDCHEBI:195528
ChEBI NameNPD6433
Stars
DefinitionAn 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.
Last Modified9 August 2023
Submitterrnash
DownloadsMolfile
FormulaC21H21N5O3
Net Charge0
Average Mass391.431
Monoisotopic Mass391.16444
SMILESCOC(=O)c1nc2ccccc2c1/N=N/N1C[C@@H]2C[C@H](C1)c1cccc(=O)n1C2
InChIInChI=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+
InChIKeyIXWNPEOFLGJGLY-WCWDXBQESA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
ChEBI Ontology
Outgoing Relation(s)
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
Citations