CHEBI:65599 - cathestatin A

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ChEBI Name cathestatin A
ChEBI ID CHEBI:65599
Definition A dicarboxylic acid monoamide obtained by the formal condensation of the carboxylic group of oxirane-2,3-dicarboxylic acid with the amino group of N-(4-aminobutyl)-L-phenylalaninamide (the 2S,3S stereoisomer). An antibiotic isolated from the fermentation broth of Penicillium citrinum, it acts as a potent inhibitor of cysteine protease.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H23N3O5
Net Charge 0
Average Mass 349.38160
Monoisotopic Mass 349.16377
InChI InChI=1S/C17H23N3O5/c18-8-4-5-9-19-15(21)12(10-11-6-2-1-3-7-11)20-16(22)13-14(25-13)17(23)24/h1-3,6-7,12-14H,4-5,8-10,18H2,(H,19,21)(H,20,22)(H,23,24)/t12-,13-,14-/m0/s1
InChIKey ZERGYHMBBZCBJM-IHRRRGAJSA-N
SMILES NCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H]1O[C@@H]1C(O)=O
Metabolite of Species Details
Penicillium citrinum (NCBI:txid5077) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
cysteine protease inhibitor
Any protease inhibitor that restricts the action of a cysteine protease.
Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cathestatin A (CHEBI:65599) has role Penicillium metabolite (CHEBI:76964)
cathestatin A (CHEBI:65599) has role antimicrobial agent (CHEBI:33281)
cathestatin A (CHEBI:65599) has role cysteine protease inhibitor (CHEBI:64152)
cathestatin A (CHEBI:65599) is a dicarboxylic acid monoamide (CHEBI:35735)
cathestatin A (CHEBI:65599) is a epoxide (CHEBI:32955)
cathestatin A (CHEBI:65599) is a monocarboxylic acid (CHEBI:25384)
cathestatin A (CHEBI:65599) is a primary amino compound (CHEBI:50994)
IUPAC Name
(2S,3S)-3-({(2S)-1-[(4-aminobutyl)amino]-1-oxo-3-phenylpropan-2-yl}carbamoyl)oxirane-2-carboxylic acid
Manual Xref Database
8103948 ChemSpider
View more database links
Registry Number Type Source
7229726 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
7766039 PubMed citation Europe PMC
8642005 PubMed citation Europe PMC
Last Modified
05 March 2014