cathestatin A (CHEBI:65599)

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CHEBI:65599 - cathestatin A

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ChEBI ID	CHEBI:65599
ChEBI Name	cathestatin A
Stars
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.
Last Modified	5 March 2014
Downloads	Molfile

Formula	C17H23N3O5
Net Charge	0
Average Mass	349.387
Monoisotopic Mass	349.16377
SMILES	NCCCCNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H]1O[C@@H]1C(=O)O
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

Species of Metabolite	Component	Source	Comments
Penicillium citrinum (ncbitaxon:5077)	-	PubMed (7766039)

Roles Classification

Chemical Roles:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium. cysteine protease inhibitor Any protease inhibitor that restricts the action of a cysteine protease. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

ChEBI Ontology

Outgoing Relation(s)
	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 Xrefs	Databases
8103948	ChemSpider

Registry Numbers	Sources
Reaxys:7229726	Reaxys

Citations