MiMeDB: Showing metabocard for S-ethyl-L-cysteine (MMDBc0054660)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:23:05 UTC

Update Date

2025-10-07 16:04:19 UTC

Metabolite ID

MMDBc0054660

Metabolite Identification

Common Name

S-ethyl-L-cysteine

Description

S-ethyl-L-cysteine is a member of the organosulfur compounds class, characterized by the presence of a sulfur atom bonded to an ethyl group and an amino acid backbone. Its chemical structure features a thiol group (-SH) that is crucial for its reactivity and biological interactions. S-ethyl-L-cysteine is involved in various biochemical pathways, including the modulation of nitric oxide signaling and the regulation of lipid metabolism, particularly through its interaction with the PCSK-9/LDL receptor axis, which is significant in managing metabolic syndrome induced by high carbohydrate and high-fat diets (PMID:39225240 ). Additionally, it has been studied for its protective effects against endoplasmic reticulum stress-induced neurotoxicity, demonstrating greater potency than its analogs in neuronal cultures (PMID:32010340 ). Furthermore, S-ethyl-L-cysteine has been utilized in chemical modification approaches, indicating its versatility in synthetic chemistry (PMID:35532550 ). Its role as a substrate in enzymatic reactions has also been highlighted, suggesting its importance in metabolic pathways (PMID:30082510 ). Overall, S-ethyl-L-cysteine serves as a significant compound in both chemical and biological contexts.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Amino-3-(ethylsulfanyl)propanoate	Generator
(2R)-2-Amino-3-(ethylsulphanyl)propanoate	Generator
(2R)-2-Amino-3-(ethylsulphanyl)propanoic acid	Generator
3-(ethylthio)Alanine	MeSH
S-Ethylcysteine	MeSH
S-Ethylcysteine, (L)-isomer	MeSH

Molecular Formula

C₅H₁₁NO₂S

Average Mass

149.211

Monoisotopic Mass

149.051049291

IUPAC Name

(2R)-2-amino-3-(ethylsulfanyl)propanoic acid

Traditional Name

(2R)-2-amino-3-(ethylsulfanyl)propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C5H11NO2S/c1-2-9-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

InChI Key

ULXKXLZEOGLCRJ-BYPYZUCNSA-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
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Sulfenyl compound
Dialkylthioether
Carbonyl group
Amine
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	30.4 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.2	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	37.67 m³·mol⁻¹	ChemAxon
Polarizability	15.59 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	465.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	315.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	157.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	289.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	279.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	342.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	935.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	624.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	795.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	186.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	355.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	200.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	52.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	270.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	510.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	57.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	218.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (void)	2025-10-24	848.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	677.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	S-ethyl-L-cysteine_TMS_1	CCSC[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1860.0
Gas Chromatography	S-ethyl-L-cysteine_TMS_2	CCSC[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1688.79
Gas Chromatography	S-ethyl-L-cysteine_TMS_3	CCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1814.67
Gas Chromatography	S-ethyl-L-cysteine_TMS_4	CCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1620.46
Gas Chromatography	S-ethyl-L-cysteine_TMS_5	CCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1407.89
Gas Chromatography	S-ethyl-L-cysteine_TMS_1	CCSC[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1766.79
Gas Chromatography	S-ethyl-L-cysteine_TMS_2	CCSC[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2199.8
Gas Chromatography	S-ethyl-L-cysteine_TMS_3	CCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1796.4
Gas Chromatography	S-ethyl-L-cysteine_TMS_4	CCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2448.44
Gas Chromatography	S-ethyl-L-cysteine_TMS_5	CCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2437.32

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for S-ethyl-L-cysteine (MMDBc0054660)

MOL for #<Metabolite:0x00007f9a9534a120>

3D MOL for #<Metabolite:0x00007f9a9534a120>

3D SDF for #<Metabolite:0x00007f9a9534a120>

3D-SDF for #<Metabolite:0x00007f9a9534a120>

PDB for #<Metabolite:0x00007f9a9534a120>

3D PDB for #<Metabolite:0x00007f9a9534a120>

SMILES for #<Metabolite:0x00007f9a9534a120>

INCHI for #<Metabolite:0x00007f9a9534a120>

Structure for #<Metabolite:0x00007f9a9534a120>

3D Structure for #<Metabolite:0x00007f9a9534a120>