MiMeDB: Showing metabocard for S-Carboxymethyl-L-cysteine (MMDBc0031758)

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:48:07 UTC

Update Date

2024-10-09 23:38:44 UTC

Metabolite ID

MMDBc0031758

Metabolite Identification

Common Name

S-Carboxymethyl-L-cysteine

Description

S-Carboxymethyl-L-cysteine is the side-chain carboxymethyl derivative of cysteine. It is produced during the metabolism of 3-chloro-L-alanine via the enzyme Cysteine synthase A. The reaction is 3-chloro-alanine + thioglycolate = S-carboxymethyl-L-cysteine + chloride.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(L)-2-Amino-3-(carboxymethylthio)propionic acid	ChEBI
(R)-S-(Carboxymethyl)cysteine	ChEBI
Carbocisteina	ChEBI
Carbocisteinum	ChEBI
Carbocysteine	ChEBI
L-3-((Carboxymethyl)thio)alanine	ChEBI
L-Carbocisteine	ChEBI
Mucodyne	ChEBI
S-(Carboxymethyl)-(R)-cysteine	ChEBI
S-Carboxymethylcysteine	ChEBI
(L)-2-Amino-3-(carboxymethylthio)propionate	Generator
Carbocisteine	ChEBI
L-Isomer carbocysteine	MeSH
Mucodine	MeSH
3-(carboxymethylthio)Alanine	MeSH
Carbocysteine, L isomer	MeSH
Mukodin	MeSH
S-(Carboxymethyl)-L-cysteine	MeSH
Carbocysteine, L-isomer	MeSH
Rhinathiol	MeSH
S Carboxymethylcysteine	MeSH
Thiodril	MeSH

Molecular Formula

C₅H₉NO₄S

Average Mass

179.194

Monoisotopic Mass

179.025228471

IUPAC Name

(2R)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid

Traditional Name

carbocisteine

CAS Registry Number

2387-59-9

SMILES

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

InChI Identifier

InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:16163 )
L-cysteine thioether (CHEBI:16163 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	21.6 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-3.3	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	1.84	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	39.11 m³·mol⁻¹	ChemAxon
Polarizability	16.69 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9530000000-8e6125018eb1d194853b	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-4900000000-be70a21dba38823e65e0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-4938b5336a3e3dd8ef9d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-2e03758abd92fb012326	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-14a74cb7928bcc5929f0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0005-9000000000-c17875b6b7ae40cc59f7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0006-9000000000-c4d5bc66488a8c749f2c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-0900000000-a9d785fbb33e2697f96a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-1900000000-2819ca720ebc627de3cd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ir9-9400000000-4b365357562747ccc151	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0229-9000000000-dd36050965c88158d31b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03k9-9000000000-dc423269c034eeee7369	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01p9-9800000000-667bc6a74e6ab57aec38	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-01p9-4900000000-643ad96ca5ded235eff4	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-2900000000-3125c68407eed34d9654	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9500000000-ae4a2feb1a0541a5f6f0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-9100000000-611fe19d8bc07f2ccc36	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01tc-4900000000-ea145a8cbe7b28667330	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-3da087ea0d68c7cacd26	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007c-9000000000-c648cd0af81d99915af5	2015-09-15	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)	2025-10-23	447.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	239.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	78.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	345.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	302.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	354.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	943.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	670.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	1080.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	187.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	280.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	210.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	46.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	427.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	741.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	102.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	232.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1006.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	683.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_1	C[Si](C)(C)OC(=O)CSC[C@H](N)C(=O)O	standard non polar	2025-10-24	1876.21
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CSCC(=O)O	standard non polar	2025-10-24	1731.8
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_3	C[Si](C)(C)N[C@@H](CSCC(=O)O)C(=O)O	standard non polar	2025-10-24	1891.02
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_4	C[Si](C)(C)OC(=O)CSC[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2511.17
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_5	C[Si](C)(C)N[C@@H](CSCC(=O)O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1796.16
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_6	C[Si](C)(C)N[C@@H](CSCC(=O)O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2194.77
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_7	C[Si](C)(C)N([C@@H](CSCC(=O)O)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1685.39
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_8	C[Si](C)(C)N[C@@H](CSCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1438.43
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_9	C[Si](C)(C)OC(=O)CSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1748.8
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_10	C[Si](C)(C)OC(=O)[C@H](CSCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2122.22
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_11	C[Si](C)(C)OC(=O)CSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1886.46
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_1	C[Si](C)(C)OC(=O)CSC[C@H](N)C(=O)O	standard polar	2025-10-24	2408.88
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_2	C[Si](C)(C)OC(=O)[C@@H](N)CSCC(=O)O	standard polar	2025-10-24	1908.91
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_3	C[Si](C)(C)N[C@@H](CSCC(=O)O)C(=O)O	standard polar	2025-10-24	2065.04
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_4	C[Si](C)(C)OC(=O)CSC[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2271.29
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_5	C[Si](C)(C)N[C@@H](CSCC(=O)O[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2082.68
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_6	C[Si](C)(C)N[C@@H](CSCC(=O)O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2543.7
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_7	C[Si](C)(C)N([C@@H](CSCC(=O)O)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2202.83
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_8	C[Si](C)(C)N[C@@H](CSCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1208.29
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_9	C[Si](C)(C)OC(=O)CSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1222.79
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_10	C[Si](C)(C)OC(=O)[C@H](CSCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2006.07
Gas Chromatography	S-Carboxymethyl-L-cysteine_TMS_11	C[Si](C)(C)OC(=O)CSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1728.42

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Name	SMPDB/PathBank	Species
Valine Biosynthesis

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	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620

External Links

HMDB ID

Not Available

DrugBank ID

DB04339

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03727

BioCyc ID

CPD-44

BiGG ID

Not Available

Wikipedia Link

Carbocisteine

METLIN ID

Not Available

PubChem Compound

193653

PDB ID

Not Available

ChEBI ID

16163

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-Carboxymethyl-L-cysteine (MMDBc0031758)

MOL for #<Metabolite:0x00007f9ab898d488>

3D MOL for #<Metabolite:0x00007f9ab898d488>

3D SDF for #<Metabolite:0x00007f9ab898d488>

3D-SDF for #<Metabolite:0x00007f9ab898d488>

PDB for #<Metabolite:0x00007f9ab898d488>

3D PDB for #<Metabolite:0x00007f9ab898d488>

SMILES for #<Metabolite:0x00007f9ab898d488>

INCHI for #<Metabolite:0x00007f9ab898d488>

Structure for #<Metabolite:0x00007f9ab898d488>

3D Structure for #<Metabolite:0x00007f9ab898d488>