L-cystathionine (CHEBI:17482)

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ChEBI Name	L-cystathionine

ChEBI ID	CHEBI:17482

ChEBI ASCII Name	L-cystathionine

Definition	A modified amino acid generated by enzymic means from L-homocysteine and L-serine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:21259, CHEBI:6205, CHEBI:13093

Supplier Information	ChemicalBook:CB6446239, eMolecules:484172, ZINC000001532680

Download	Molfile XML SDF

Wikipedia	License
Cystathionine is an intermediate in the synthesis of cysteine from homocysteine. It is produced by the transsulfuration pathway and is converted into cysteine by cystathionine gamma-lyase (CTH). Biosynthetically, cystathionine is generated from homocysteine and serine by cystathionine beta synthase (upper reaction in the diagram below). It is then cleaved into cysteine and α-ketobutyrate by cystathionine gamma-lyase (lower reaction). An excess of cystathionine in the urine is called cystathioninuria . Cysteine dioxygenase (CDO), and sulfinoalanine decarboxylase can turn cysteine into hypotaurine and then taurine. Alternately, the cysteine from the cystathionine gamma-lyase can be used by the enzymes glutamate–cysteine ligase (GCL) and glutathione synthetase (GSS) to produce glutathione.
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Formula

C7H14N2O4S

Net Charge

Average Mass

222.26314

Monoisotopic Mass

222.06743

InChI

InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1

InChIKey

ILRYLPWNYFXEMH-WHFBIAKZSA-N

SMILES

N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via cystathionine )

ChEBI Ontology
Outgoing	L-cystathionine (CHEBI:17482) has role Escherichia coli metabolite (CHEBI:76971) L-cystathionine (CHEBI:17482) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-cystathionine (CHEBI:17482) has role human metabolite (CHEBI:77746) L-cystathionine (CHEBI:17482) has role mouse metabolite (CHEBI:75771) L-cystathionine (CHEBI:17482) is a cystathionine (CHEBI:17755) L-cystathionine (CHEBI:17482) is tautomer of L-cystathionine dizwitterion (CHEBI:58161)

Incoming	L-cystathionine dizwitterion (CHEBI:58161) is tautomer of L-cystathionine (CHEBI:17482)

IUPAC Names

(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid

L-cystathionine

Synonyms	Sources
(R)-S-(2-amino-2-carboxyethyl)-L-Homocysteine	HMDB
L-(+)-Cystathionine	ChemIDplus
L-Cystathionine	KEGG COMPOUND
S-(beta-amino-beta-carboxyethyl)homocysteine	ChEBI

Citation

Last Modified

27 January 2016