FComEx: L-Cystathionine (PC000266)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:35 UTC

Update date

2017-01-19 02:36:18 UTC

FoodComEx ID

PC000266

FoodDB Record

FDB001976

Chemical Information

Name

L-Cystathionine

Description

Isolated from Phallus impudicus (common stinkhorn) Cystathionine is a dipeptide formed by serine and homocysteine. Cystathioninuria is a prominent manifestation of vitamin-B6 deficiency. The transsulfuration of methionine yields homocysteine, which combines with serine to form cystathionine, the proximate precursor of cysteine through the enzymatic activity of cystathionase. In conditions in which cystathionine gamma-synthase or cystathionase is deficient, for example, there is cystathioninuria. Although cystathionine has not been detected in normal human serum or plasma by most conventional methods, gas chromatographic/mass spectrometric methodology detected a mean concentration of cystathionine in normal human serum of 140 nM, with a range of 65 to 301 nM.567 Cystathionine concentrations in CSF have been 10, 1, and 0.5 uM, and "not detected." Only traces (i.e., <1 uM) of cystathionine are present in normal CSF.587. gamma-Cystathionase deficiency provided the first instance in which, in a human, the major biochemical abnormality due to a defined enzyme defect was clearly shown to be alleviated by administration of large doses of pyridoxine. The response in gamma-cystathionase-deficient patients is not attributable to correction of a preexisting deficiency of this vitamin. (OMMBID, Chap. 88); Cystathionine is an intermediate in the synthesis of cysteine. L-Cystathionine is found in many foods, some of which are spirulina, greenthread tea, gooseberry, and quinoa.

CAS Number

56-88-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(R)-S-(2-amino-2-carboxyethyl)-L-Homocysteine	biospider
[R-(R,s)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoate	HMDB
[R-(R,s)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoic acid	HMDB
Cystathionine	biospider
Cystathionine (6CI,7CI)	biospider
Cystathionine, l-	biospider
Cystathionine, L- (8CI)	biospider
L-(+)-cystathionine	biospider
L-Cystathionine	db_source
L-Homocysteine, S-((2R)-2-amino-2-carboxyethyl)-	biospider
L-Homocysteine, S-(2-amino-2-carboxyethyl)-, (R)-	biospider
L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]-	biospider
L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]- (9CI)	biospider
S-(b-amino-b-Carboxyethyl)homocysteine	Generator
S-(beta-amino-beta-carboxyethyl)homocysteine	biospider
S-(β-amino-β-carboxyethyl)homocysteine	Generator
S-[(2R)-2-amino-2-carboxyethyl]-L-Homocysteine	biospider

Chemical Formula

C7H14N2O4S

IUPAC name

2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

InChI Identifier

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)

InChI Key

ILRYLPWNYFXEMH-UHFFFAOYSA-N

Isomeric SMILES

NC(CCSCC(N)C(O)=O)C(O)=O

Average Molecular Weight

222.262

Monoisotopic Molecular Weight

222.067427636

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents