P. aeruginosa Metabolome Database: Cysteic acid (PAMDB000464)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000464

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 View Structure

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

Average Molecular Weight:

169.156

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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
Alkanesulfonic acid
Sulfonyl
Sulfonic acid derivative
Sulfonic acid
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	73.6 mg/mL	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

Pathways:

Cysteine and methionine metabolism pae00270
Taurine and hypotaurine metabolism pae00430

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
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

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

• 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
Locus Tag:: PA3443
Molecular weight:: 28.5 kDa

Transporters

Protein Details

• 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
Locus Tag:: PA3443
Molecular weight:: 28.5 kDa

Cysteic acid (PAMDB000464)

Structure for Cysteic acid (PAMDB000464)

Enzymes

Transporters