ContaminantDB: Carbocysteine

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

Record Information

Version

1.0

Creation Date

2016-05-22 03:38:19 UTC

Update Date

2016-11-09 01:15:26 UTC

Accession Number

CHEM016606

Identification

Common Name

Carbocysteine

Class

Small Molecule

Description

S-carboxymethylcysteine (carbocisteine) is the most frequently prescribed mucoactive agent for long-term COPD (chronic obstructive pulmonary disease) use in a number of countries. In addition to its mucoregulatory activity, carbocisteine exhibits free-radical scavenging and anti-inflammatory properties. S-Carboxymethyl-L-cysteine can be found in root vegetables and has been isolated from radish seedlings. S-carboxymethyl-L-cysteine can be detectable in urine especially after the processing of chlorinated compounds by gut microlfora.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Carbocisteine	Kegg
Mucofan	Kegg
(L)-2-Amino-3-(carboxymethylthio)propionic acid	HMDB
(R)-S-(Carboxymethyl)cysteine	HMDB
1-Carboxymethylcysteine	HMDB
2-Amino-3-(carboxymethylthio)propionic acid	HMDB
2-Amino-3-[(carboxymethyl)sulfanyl]propanoic acid	HMDB
3-((Carboxymethyl)thio)alanine	HMDB
3-(Carboxymethylthio)-L-alanine	HMDB
3-(Carboxymethylthio)alanine	HMDB
3-[(Carboxymethyl)thio]-L-alanine	HMDB
3-[(Carboxymethyl)thio]alanine	HMDB
5-Amino-3-thiadihexanoic acid	HMDB
Carboxymethylated cysteine	HMDB
Carboxymethylcysteine	HMDB
Carboxymethylenecysteine	HMDB
L-3-((Carboxymethyl)thio)alanine	HMDB
L-Carboxymethylcysteine	HMDB
Loviscol	HMDB
Muciclar	HMDB
Mucocis	HMDB
Mucodine	HMDB
Mucodyne	HMDB
Reomucil	HMDB
Rhinathiol	HMDB
S-(Carboxymethyl)-(R)-cysteine	HMDB
S-(Carboxymethyl)-L-cysteine	HMDB
S-(Carboxymethyl)cysteine	HMDB
S-Carboxylmethyl-L-cysteine	HMDB
S-Carboxymethylcysteine	HMDB
Thiodril	HMDB
Carbocysteine, L-isomer	HMDB
S Carboxymethylcysteine	HMDB
Mukodin	HMDB
Carbocysteine, L isomer	HMDB
L-Isomer carbocysteine	HMDB

Chemical Formula

C₅H₉NO₄S

Average Molecular Mass

179.194 g/mol

Monoisotopic Mass

179.025 g/mol

CAS Registry Number

2387-59-9

IUPAC Name

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

Traditional Name

carbocystein

SMILES

NC(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)

InChI Key

GBFLZEXEOZUWRN-UHFFFAOYSA-N

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

Substituents

Cysteine or derivatives
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
Hydrocarbon derivative
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

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

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	16.66 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05mk-1920000000-1bfde05bf74ad952988c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gba-0950000000-3deefa0cf048f58da5b7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05mk-1920000000-1bfde05bf74ad952988c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0gba-0950000000-3deefa0cf048f58da5b7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-c20980f00a00f1e6e180	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05g4-9650000000-0aed012631a77de5b93a	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	splash10-001i-3900000000-33a818ac062af18410a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9500000000-c7b2a3062072d67fbc4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-9100000000-0e0a6581889fafc8e6d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004l-6900000000-ee309c95fd84852db457	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-396c0c726a8b135b8da4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-5243edfeeee8b8e7df3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-2205efc680b90ef8e86d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-9000000000-c2902dceba4c5c456423	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-9000000000-95016c8505c678c2d2ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-8900000000-5572c3ac9193ded60872	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-9100000000-f93524089b1962d1a05c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-3faa3225eb4898645240	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)

Not Available

Uses/Sources

Not Available

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

HMDB0029415

FooDB ID

FDB000507

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Carbocysteine (CHEM016606)

Structure for CHEM016606: Carbocysteine