ContaminantDB: 3-Mercaptolactate-cysteine disulfide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:50:59 UTC

Update Date

2026-04-06 12:17:21 UTC

Accession Number

CHEM003363

Identification

Common Name

3-Mercaptolactate-cysteine disulfide

Class

Small Molecule

Description

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 (1, 2, 3, 4).

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 Mass

241.285 g/mol

Monoisotopic Mass

241.008 g/mol

CAS Registry Number

18841-42-4

IUPAC Name

Not Available

Traditional Name

hcetc

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

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Beta-mercaptolactate-cysteine disulfiduria	SMP00499	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9300000000-68e01abf228e831fed45	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-9533100000-d4f0ecb6cd097f65b9dd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006w-1960000000-f56bf92526e8f726becf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ds-3910000000-c2b2312a5af041580ab5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-7900000000-a49dadf9d375535e0dce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-4950000000-6b12c4c4f730b800e73b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xr-6900000000-ec3b44873b06061157f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-9200000000-c80fb1c7de58ac714124	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0g4i-2900000000-368301025d75cd74dd85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0230-9500000000-6b2727915ff92bbf8cf0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-047m-9100000000-3c559c5d78dfba6464a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0890000000-8babd75cca365d589ef6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6900000000-6b7f3b667ac4477205d0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-e35fd1cdef28827b87aa	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0006512

FooDB ID

FDB023951

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

2742951

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

167948

ChEBI ID

140723

PubChem Compound ID

193536

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

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.

MSDS

Not Available

General References

1. 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.

2. Crawhall JC: A review of the clinical presentation and laboratory findings in two uncommon hereditary disorders of sulfur amino acid metabolism, beta-mercaptolactate cysteine disulfideuria and sulfite oxidase deficiency. Clin Biochem. 1985 Jun;18(3):139-42.

3. Hannestad U, Sorbo B: Determination of 3-mercaptolactate, mercaptoacetate and N-acetylcysteine in urine by gas chromatography. Clin Chim Acta. 1979 Jul 16;95(2):189-200.

4. Hannestad U, Martensson J, Sjodahl R, Sorbo B: 3-mercaptolactate cysteine disulfiduria: biochemical studies on affected and unaffected members of a family. Biochem Med. 1981 Aug;26(1):106-14.

5. Crawhall JC, Parker R, Sneddon W, Young EP, Ampola MG, Efron ML, Bixby EM: Beta mercaptolactate-cysteine disulfide: analog of cystine in the urine of a mentally retarded patient. Science. 1968 Apr 26;160(3826):419-20.

6. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.

3-Mercaptolactate-cysteine disulfide (CHEM003363)

Structure for CHEM003363: 3-Mercaptolactate-cysteine disulfide