(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethanesulfonyl]sulfanyl}propanoic acid

• ChemBase ID: 165323
• Molecular Formular: C6H12N2O6S2
• Molecular Mass: 272.29928
• Monoisotopic Mass: 272.01367811
• SMILES: [C@@H](CSS(=O)(=O)C[C@H](N)C(=O)O)(N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CSS(=O)(=O)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H12N2O6S2/c7-3(5(9)10)1-15-16(13,14)2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
• InChIKey: RXQXJZDPDXVIEN-IMJSIDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethanesulfonyl]sulfanyl}propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethanesulfonyl]sulfanyl}propanoic acid
• Synonyms: L-Cysteine S,S-Dioxide; Cystine S-Dioxide; Cystine Dioxide; Cystine Disulfoxide; 3-(Thiosulfo)-L-alanine S-Ester with L-Cysteine; L-Cysteine S-Ester with 3-(Thiosulfo)-L-alanine; Sacsyl-cysteine; L-Cysteine Sulfone

Database IDs

• CAS Number: 30452-69-8
• PubChem SID: 162259456
• PubChem CID: 36689204

CALCULATED PROPERTIES

• Acid pKa: 0.9671286
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -6.9031825
• LogD (pH = 7.4): -6.946924
• Log P: -6.9028997
• Molar Refractivity: 55.3063 cm^3
• Polarizability: 23.486668 Å^3
• Polar Surface Area: 160.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - C997825

L-Cysteine Sulfone is a metabolite of L-Cystine.

REFERENCES

• Toennies, G., et al.: J. Biol. Chem., 113, 571 (1936)