CHEBI:17482 - L-cystathionine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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:CB2127503, eMolecules:29913760, eMolecules:474683, Selleckchem:Acetylcysteine, ZINC000003589203
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N-acetylcysteine, also known as Acetylcysteine and NAC, is a medication that is used to treat paracetamol (acetaminophen) overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders, such as pneumonia and bronchitis. It has been used to treat lactobezoar in infants. It can be taken intravenously, orally (swallowed by mouth), or inhaled as a mist by use of a nebulizer. It is also sometimes used as a dietary supplement. Common side effects include nausea and vomiting when taken orally. The skin may occasionally become red and itchy with any route of administration. A non-immune type of anaphylaxis may also occur. It appears to be safe in pregnancy. For paracetamol overdose, it works by increasing the level of glutathione, an antioxidant that can neutralize the toxic breakdown products of paracetamol. When inhaled, it acts as a mucolytic by decreasing the thickness of mucus. Acetylcysteine was initially patented in 1960 and came into medical use in 1968. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids.
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Formula C7H14N2O4S
Net Charge 0
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 )
View more via ChEBI Ontology
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
Manual Xrefs Databases
C00007498 KNApSAcK
C02291 KEGG COMPOUND
Cystathionine Wikipedia
CYSTATHIONINE MetaCyc
HMDB0000099 HMDB
View more database links
Registry Numbers Types Sources
2331423 Reaxys Registry Number Reaxys
56-88-2 CAS Registry Number KEGG COMPOUND
Citation Type Source
1025897 PubMed citation Europe PMC
Last Modified
27 January 2016