ChemFOnt: Showing chemical card for 3-Mercaptolactate-cysteine disulfide (CFc000002782)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:44 UTC

Chemfont ID

CFc000002782

Molecule Identification

Common Name

3-Mercaptolactate-cysteine disulfide

Definition

3-mercaptolactate-cysteine disulfide is a compound analog of cysteine excreted in the urine of patients affected by Mercaptolactate-cysteine disulfiduria (MCDU, OMIM 249650 ), the product of disorder of sulfur amino acid metabolism and a reduced activity of the enzyme mercaptopyruvate sulfurtransferase (MST, EC 2.8.1.2). Reduction of protein in the diet, addition of pyridoxine or of neomycin did not affect the urinary excretion of beta-mercaptolactate-cysteine disulfide of a mentally defective patient who was excreting this mixed disulfide. Addition of cysteine to the diet did increase the excretion of this disulfide (PMID: 3888441 , 527218 , 6945862 , 5644041 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Mercaptolactate-cysteine disulphide	Generator
3-Mercaptolactic acid-cysteine disulfide	Generator
3-Mercaptolactic acid-cysteine disulphide	Generator
S-(2-Hydroxy-2-carboxyethylthio)cysteine	MeSH
beta-Mercaptolactate cysteine disulfide	MeSH
3-((2-Carboxy-2-hydroxyethyl)dithio)-L-alanine	HMDB
Hcetc	HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-hydroxypropanoate	Generator, HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulphanyl}-2-hydroxypropanoate	Generator, HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulphanyl}-2-hydroxypropanoic acid	Generator, HMDB
3-Mercaptolactate-cysteine disulfide	MeSH

Chemical Formula

C₆H₁₁NO₅S₂

Average Molecular Weight

241.285

Monoisotopic Molecular Weight

241.007863847

IUPAC Name

3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-hydroxypropanoic acid

Traditional Name

hcetc

CAS Registry Number

18841-42-4

SMILES

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

InChI Identifier

InChI=1S/C6H11NO5S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4,8H,1-2,7H2,(H,9,10)(H,11,12)/t3-,4?/m0/s1

InChI Key

MAFDYIDMXCXBRB-WUCPZUCCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-cysteine-S-conjugates

Alternative Parents

Substituents

L-cysteine-s-conjugate
Alpha-amino acid
L-alpha-amino acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Amino acid
Dialkyldisulfide
Organic disulfide
Secondary alcohol
Carboxylic acid
Sulfenyl compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0006512)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Beta-Mercaptolactate-Cysteine Disulfiduria (HMDB: HMDB0006512)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	28.3 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.6	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.68	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.85 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	53.21 m³·mol⁻¹	ChemAxon
Polarizability	22.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006512

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023951

KNApSAcK ID

Not Available

Chemspider ID

167948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2742951

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193536

PDB ID

Not Available

ChEBI ID

140723

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kobayashi, Kanji; Ikegami, Takuma; Ubuka, Toshihiko. New metabolites of cystine. II. Chemical and biochemical properties of S-(2-oxo-2-carboxyethylthio)cysteine. Physiological Chemistry and Physics (1973), 5(2), 167-71.

Showing chemical card for 3-Mercaptolactate-cysteine disulfide (CFc000002782)

MOL for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

3D MOL for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

3D SDF for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

3D-SDF for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

PDB for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

3D PDB for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

SMILES for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

INCHI for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

Structure for CFc000002782 (3-Mercaptolactate-cysteine disulfide)

3D Structure for CFc000002782 (3-Mercaptolactate-cysteine disulfide)