ECMDB: Cysteic acid (ECMDB02757) (M2MDB000464)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)Transporters (1)XML

Proteins (523)

Record Information

Version

2.0

Creation Date

2012-05-31 13:57:02 -0600

Update Date

2015-09-13 12:56:12 -0600

Secondary Accession Numbers

ECMDB02757

Identification

Name:

Cysteic acid

Description

Cysteic acid is an amino acid formed in the oxidation of cysteine; it is a precursor of taurine.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2R)-2-amino-3-sulfopropanoate
(2R)-2-amino-3-sulfopropanoic acid
(2R)-2-amino-3-sulphopropanoate
(2R)-2-amino-3-sulphopropanoic acid
2-Amino-3-sulfopropanoate
2-Amino-3-sulfopropanoic acid
2-Amino-3-sulfopropionate
2-Amino-3-sulfopropionic acid
2-Amino-3-sulphopropanoate
2-Amino-3-sulphopropanoic acid
2-Amino-3-sulphopropionate
2-Amino-3-sulphopropionic acid
3-Sulfo-L-alanine
3-Sulfoalanine
3-Sulpho-L-alanine
3-Sulphoalanine
b-Sulfoalanine
b-Sulphoalanine
Beta-Sulfoalanine
Beta-Sulphoalanine
Cepteate
Cepteic acid
Cipteate
Cipteic acid
Cysteate
Cysteic acid
Cysteinate
Cysteinesulfonate
Cysteinesulfonic acid
Cysteinesulphonate
Cysteinesulphonic acid
Cysteinic acid
Cysterate
Cysteric acid
L-Cysteate
L-Cysteic acid
β-Sulfoalanine
β-Sulphoalanine

Chemical Formula:

C₃H₇NO₅S

Weight:

Average: 169.156
Monoisotopic: 169.004493029

InChI Key:

XVOYSCVBGLVSOL-UHFFFAOYSA-N

InChI:

InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)

CAS number:

498-40-8

IUPAC Name:

2-amino-3-sulfopropanoic acid

Traditional IUPAC Name:

cysteic acid

SMILES:

NC(CS(O)(=O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:21260 )
amino sulfonic acid (CHEBI:21260 )
alanine derivative (CHEBI:21260 )
carboxyalkanesulfonic acid (CHEBI:21260 )
cysteine derivative (CHEBI:21260 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	73.6 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3	ChemAxon
logS	-0.36	ALOGPS
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.43 m³·mol⁻¹	ChemAxon
Polarizability	13.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Cysteic acid <> Taurine + Carbon dioxide
Cysteic acid + alpha-Ketoglutarate <> 3-Sulfopyruvic acid + L-Glutamate
Cysteic acid + Cysteic acid > Taurine + Carbon dioxide
Cysteic acid + Oxoglutaric acid <> L-Glutamate + 3-Sulfopyruvic acid

SMPDB Pathways:

Collection of Reactions without pathways

PW001891

KEGG Pathways:

Cysteine and methionine metabolism ec00270
Taurine and hypotaurine metabolism ec00430

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-4987d9a40ecc2c214dc3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9200000000-63aac0a32cfc85b50ddd	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-e495810d64e3e38da2bd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uxr-0900000000-02df293f7975b82ac3b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-47bca80f8407522228fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9100000000-45eccf44b0be54ef5703	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-9800000000-32b77b0eb11d32fe32bd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-47bca80f8407522228fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-6103b341ba1eeaf705ef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-b3cbcae68d66f83d26cc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0159-9800000000-c9f345d26f9e3b45c607	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-e31af2162892af224283	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-d763c2e7d917148c530c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-0158ea55e5c9dfde9dc7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0089-9000000000-510d6054b2f3b09e2920	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-cfa2835cc0b2b29ec110	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-aa53bbb90f5cdd3a6d83	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0abc-3900000000-0626b1961d0517861451	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-29ef424c41f3119ec633	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-cc1dd155bb25f8c9a20f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-2900000000-8fc583c963f43919bf50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-1900000000-00b8a4b9bbedfa9bf252	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9800000000-18c40d4b99159222b563	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-7a313e5ca76d5a55eb56	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-5900000000-967c249c15d798909745	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9200000000-c02c1daafa3bc2cec519	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-80973e7856292311a36d	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Jasin HE: Oxidative modification of inflammatory synovial fluid immunoglobulin G. Inflammation. 1993 Apr;17(2):167-81. Pubmed: 8387962
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Paroni R, De Vecchi E, Fermo I, Arcelloni C, Diomede L, Magni F, Bonini PA: Total urinary hydroxyproline determined with rapid and simple high-performance liquid chromatography. Clin Chem. 1992 Mar;38(3):407-11. Pubmed: 1547560
Sarwar G, Botting HG, Peace RW: Complete amino acid analysis in hydrolysates of foods and feces by liquid chromatography of precolumn phenylisothiocyanate derivatives. J Assoc Off Anal Chem. 1988 Nov-Dec;71(6):1172-5. Pubmed: 3240976

Synthesis Reference:

Zhao, Chong-tao; Wang, Qing-ping; Lin, Wan-zhen; Chen, Ping. Synthesis of L-cysteic acid by indirect electrooxidation. Jingxi Huagong (2003), 20(4), 237-238, 253.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	17285
HMDB ID	HMDB02757
Pubchem Compound ID	25701
Kegg ID	C00506
ChemSpider ID	23942
Wikipedia ID	Cysteic_acid
BioCyc ID	L-CYSTEATE
EcoCyc ID	L-CYSTEATE

Enzymes

Protein Details

1. Aspartate aminotransferase

General function:: Involved in transferase activity
Specific function:: L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
Gene Name:: aspC
Uniprot ID:: P00509
Molecular weight:: 43573

Reactions

L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate.

Protein Details

2. Glutamate decarboxylase alpha

General function:: Involved in glutamate decarboxylase activity
Specific function:: Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:: gadA
Uniprot ID:: P69908
Molecular weight:: 52685

Reactions

L-glutamate = 4-aminobutanoate + CO(2).

Protein Details

3. Glutamate decarboxylase beta

General function:: Involved in glutamate decarboxylase activity
Specific function:: Converts glutamate to gamma-aminobutyrate (GABA), consuming one intracellular proton in the reaction. The gad system helps to maintain a near-neutral intracellular pH when cells are exposed to extremely acidic conditions. The ability to survive transit through the acidic conditions of the stomach is essential for successful colonization of the mammalian host by commensal and pathogenic bacteria
Gene Name:: gadB
Uniprot ID:: P69910
Molecular weight:: 52668

Reactions

L-glutamate = 4-aminobutanoate + CO(2).

Protein Details

4. Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Uniprot ID:: P75851
Molecular weight:: 28925

Transporters

Protein Details

1. Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Uniprot ID:: P75851
Molecular weight:: 28925

Cysteic acid (ECMDB02757) (M2MDB000464)

Structure for #<Compound:0xac36809c>

Enzymes

Reactions

Reactions

Reactions

Transporters