(2R)-2-amino-3-sulfopropanoic acid hydrate

• ChemBase ID: 102384
• Molecular Formular: C3H9NO6S
• Molecular Mass: 187.17166
• Monoisotopic Mass: 187.01505801
• SMILES: O=C(O)[C@@H](N)CS(=O)(=O)O.O
• Canonical SMILES: OC(=O)[C@H](CS(=O)(=O)O)N.O
• InChI: InChI=1S/C3H7NO5S.H2O/c4-2(3(5)6)1-10(7,8)9;/h2H,1,4H2,(H,5,6)(H,7,8,9);1H2/t2-;/m0./s1
• InChIKey: PCPIXZZGBZWHJO-DKWTVANSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-sulfopropanoic acid hydrate
• IUPAC Traditional name: cysteinesulfonic acid hydrate
• Synonyms: β-Sulfo-L-alanine; L-2-Amino-3-sulfopropionic acid; L-CYSTEIC ACID MONOHYDRATE; 3-Sulfo-L-alanine Monohydrate; (R)-2-Amino-3-sulfopropionic acid; L-Cysteic acid monohydrate; L-氧化半胱氨酸; L-磺基丙氨酸 一水合物

Database IDs

• CAS Number: 23537-25-9
• EC Number: 207-861-3
• MDL Number: MFCD00149544
• Beilstein Number: 3714036
• PubChem SID: 24858207; 162089938
• PubChem CID: 12308854

CALCULATED PROPERTIES

• Acid pKa: -1.7161957
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -6.462623
• LogD (pH = 7.4): -6.5690074
• Log P: -2.9572992
• Molar Refractivity: 30.435 cm^3
• Polarizability: 13.2867 Å^3
• Polar Surface Area: 117.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 267 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +7.5±0.5°, c = 5% in H2O; [α]24/D +8.2°, c = 7.5 in H2O

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (T); 98%
• Linear Formula: HO3SCH2CH(NH2)CO2H·H2O

DETAILS

MP Biomedicals - 02101437

Monohydrate
Crystalline

Sigma Aldrich - 30170

Application
Internal standard for amino acid analysis.1
Biochem/physiol Actions
L-Cysteic acid is a sulfur containing aspartate analogue that may be used as a competitive inhibitor of the bacterial aspartate:alanine antiporter (AspT) exchange of aspartate and in other aspartate biological systems. L-Cysteic acid is used in monomeric surfactant development.
L-cysteic acid is an oxidation product of L-cysteine. L-Cysteic acid, an analogue of cysteine sulfinic acid, may be used in studies of excitatory amino acids in the brain, such as those that bind to cysteine sulfinic acid receptors. L-Cysteic acid is a useful agonist at several rat metabotropic glutamate receptors (mGluRs).

Toronto Research Chemicals - C994500

A major metabolite of non-essential amino acid L-Cysteine.

REFERENCES

• Parsons, R.B. et al.: Neurotoxicol., 19, 599 (1998)