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

• ChemBase ID: 61729
• Molecular Formular: C6H11NO4S
• Molecular Mass: 193.22084
• Monoisotopic Mass: 193.04087884
• SMILES: C(=O)([C@@H](N)CSCCC(=O)O)O
• Canonical SMILES: OC(=O)CCSC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H11NO4S/c7-4(6(10)11)3-12-2-1-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1
• InChIKey: FBPINGSGHKXIQA-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-[(2-carboxyethyl)sulfanyl]propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-[(2-carboxyethyl)sulfanyl]propanoic acid
• Synonyms: (2R)-2-amino-3-[(2-carboxyethyl)sulfanyl]propanoic acid; L-3-[(2-Carboxyethyl)thio]alanine; 2-Amino-4-thiaheptanedioic Acid; S-(2-Carboxyethyl)cysteine; CEC:; S-(2-Carboxyethyl)-L-cysteine; (2R)-2-Amino-3-[(2-carboxyethyl)sulfanyl]-propanoic acid

Database IDs

• CAS Number: 100429-59-2; 4033-46-9
• MDL Number: MFCD03424208
• PubChem SID: 162027470
• PubChem CID: 23618202

CALCULATED PROPERTIES

• Acid pKa: 1.9763474
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.991082
• LogD (pH = 7.4): -5.742659
• Log P: -2.8446074
• Molar Refractivity: 43.7078 cm^3
• Polarizability: 17.551321 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 191-193°C (dec.); 218 dec °C; 218°C(dec)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: >95%

DETAILS

Toronto Research Chemicals - C178055

An advanced glycation end product, found in elevated concentrations within Diabetes Mellitus patients.

REFERENCES

• Chatton, J., et al.: J. Pharmacol. Exper. Thera., 299, 1161 (2001)
• Mostafa, A., et al.: Mol. Cell. Biochem., 302, 35 (2001)